Calendar of Events for Key West

Visit Key West's historic streets and see beautiful tropical foliage in bloom all-year round.

Throughout the year Key West hosts a wide variety of events - many of which are truly unique to the island.

Depending on the time of the year, you may see walking Key West's streets: Hemingway look-alikes, Jimmy Buffet "parrotheads", pirates, motorcycle aficionados, Bahamian Junkanoo performers, world class sailors and fishermen, noted authors & writers, or scantily clad Fantasy Fest revelers. Plus, every night, is the Sunset Celebration (Key West sunset times).

Something missing?If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we'll quickly add it.

Check back frequently: more dates and details are added as the season progresses.

2013 Key West Calendar of Events

Click here to add your Key West event now.

Something missing? If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we'll quickly add it.

And check back frequently - since more dates and details will be added as the season progresses.

If you are wondering what we did last year (2012), or are trying to figure out when an event might happen again this year, here is the 2012 Key West Calendar of Events:

• January 5 - 8, 2012 - LITERATURE - 30th Annual Key West Literary Seminar - This year's theme is: Yet Another World. Features four days of readings, conversations, lectures, panel discussions, and parties. Confirmed speakers include Margaret Atwood, Billy Collins, Douglas Coupland, Michael Cunningham, Jennifer Egan, Rivka Galchen, William Gibson, James Gleick, Robert Krulwich, Jonathan Lethem, Janna Levin, Valerie Martin, China Mieville, Joyce Carol Oates, Dexter Palmer, George Saunders, Gary Shteyngart, James Tate, Colson Whitehead, and Charles Yu. Cost is $545. Advanced registration is required and is already sold out. However, there is a free session 2pm on Sunday January 8 at the San Carlos Institute at 516 Duval Street that is open to the public on a first come first served basis. For more information call 1-888-293-9291.
• January 6, 2012 - BOXING - Fight Night in the Keys - Mallory Square once again hosts an evening of professional boxing with seven bouts scheduled. This event will be broadcast live by ESPN. Tickets cost $35 for general admission, $65 for ringside, and $125 for VIP. Fighting starts at 7pm (gates open at 6pm). For more information and tickets, call 305-295-7676 between 10am and 2pm.
• January 6 - 7, 2012 - RUNNING - Ragnar Relay Florida Keys - And incredible team relay race 199 miles in length. Starts in Miami and ends in Key West with teams of twelve people competing for awards for the top three finishers in each category. Finish line is at the Southernmost Hotel at 1319 Duval Street. Registration is now closed, but call 877-83-RELAY for more information.
• January 07, 2012 - MUSIC - The Studios of Key West presents: Cheryl Wheeler in Concert  - Singer, songwriter, and storyteller whose work has been covered by Bette Middler, Dan Seals, and other noteworthy musicians. Part of TSKW's Old Town New Folk Concert Series. Tickets are $25 in advance, $30 at door. 8 p.m. 600 White Street. Call 305-296-0458 for more information.
• January 9, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Margaret Atwood - Author of many novels, collections of poetry and nonfiction works writing in the genres Romance, Historical fiction, Speculative fiction, Science fiction, and Dystopian fiction. Among her notable works are The Handmaid's Tale, Cat's Eye, Alias Grace, The Blind Assassin, Oryx and Crake, and Surfacing. 6 pm, Studios of Key West, 600 White Street. FREE.
• January 14, 2012 - SEAFOOD - 7th Annual Florida Keys Seafood Festival - Created by the local commercial fishermen association, this event features the freshest seafood served picnic style at Bayview Park in Key West. Family-friendly event improving each year, with live music and vendors. Free to attend. 11am-8pm. For more information, call 305-872-9026.
• January 15 - 20, 2012 - SAILING - 25th Annual Key West Race Week - Known locally in Key West as "race week", this world class sailing competition hosts 24 – 80 foot racing yachts from across the country and around the world as they compete for class championships in this international midwinter sailboat regatta. The view of nearly 300 sailboats underway is spectacular, and can be seen (from a distance) at Fort Zachary Taylor State Park at the end of Southard Street. Call (781) 639-9545 for more information.
• January 16, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Hal Crowther - Prolific journalist and essayist, whose most recent collection of essays, Gather at the River, was a finalist for the National Book Critics Circle and nominated for the Pulitzer Prize and the National Book Award. His collection Cathedrals of Kudzu (2000) received many awards including the Lillian Smith Book Award from the Southern Regional Council. 6pm, Studios of Key West, 600 White Street. FREE.
• January 20-22, 2012 - FISHING - Key West Harbour King Mackerel Tournament - Did you know that king mackerel (also called kingfish), is one of the fastest swimming fish in the ocean. And when hooked, they'll pull hundreds of yards of fishing line from the reel in seconds. Kingfish is also among the most competitive and rewarding fishing tournaments, with top prize of $10,000 for the biggest fish. For more information, call 305-296-0364.
• January 20 - 21, 2012 - ARCHITECTURE - 52st Annual House and Garden Tour - Visit five Key West homes and tropical gardens.  Conch Tour Train to each location is included with ticket price. Tickets are $25. Call 305-294-9501 for more information.
• January 21, 2012 - CELEBRATION - 100th Anniversary of Flagler's Railroad - Costume ball marking Henry Flagler's railroad that arrived in Key West a century ago. Cost is $100 per person. 6pm-10pm. Casa Marina Resort, 1500 Reynolds Street.
• January 22, 2012 - MUSIC - Key West Pops Orchestra Presenting Obbligato - Full sized orchestra performs music of classic greats including Mozart, Handel, and Verdi. 7:30 pm. Tennessee Williams Theater. Stock Island. For more information call 305-296-6059.
• January 22, 2012 - RUNNING - 14th Annual Key West Half Marathon Run - Runners enjoy near perfect temperatures, flat terrain, and Key West scenery in one of the most popular running races of the year. Entry fee $45, $50 day of race. Call 305-296-7182 for more information.
• January 22, 2012 - CELBERATION - Flagler Centennial Parade - A century after Henry Flagler's famous "railroad that went to the sea" arrived in Key West, a parade down Duval Street will honor the occasion. Parade starts at Higgs Beach (on the south side of the island, next to the Casa Marina), and follows Duval Street to the Custom House, which will be introducing an exhibit on the railroad.
• January 23, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Seth Bramson - Florida historian who has written many books about various aspects of Florida history including From Sandbar to Sophistication: The Story of Sunny Isles Beach (2007) and Boulevard of Dreams: A Pictorial History of El Portal, Biscayne Park, Miami Shores and North Miami (2007), but he is perhaps best known for his writings on the last railway to connect Key West with the mainland, the subject of his new book The Greatest (Railroad) Story Ever Told: Henry Flagler and the Florida East Coast Railway’s Key West Extension. 6 pm, Studios of Key West, 600 White Street. FREE.
• January 26 - 29, 2012 - FOOD - Key West Food & Wine Festival - Festival celebrating Key West's culinary delights and excellence . Offers tasting's, seminars, and island events. VIP pass cost $335. Daily events cost $40-$130. Call 800-474-4319 for more information.
• January 26 - 29, 2012 - MUSIC - Third Annual Key West Dulcimer Festival - What is a dulcimer, you say? The dulcimer is a stringed musical instrument, with origins dating back 2000 years. It has a very traditional, seafaring sort of sound. Celebrating this traditional instrument, the plucky musicians are back and ready for another year of great performances, including dulcimer, guitar, banjo, and autoharp. Thirty-one workshops are planned, and cost $15 to $20 each. The four-day festival is to be held at Hurricane Hole Marina, MM 4.5 oceanside.
• January 28, 2012 - ARTS - Anne McKee Artists Fund Auction - Bid on Key west art knowing that the proceeds benefit Keys artists and projects. You'll see work in all media - including oil painting, acrylic painting, sculpture, jewelry, and ceramics. Art Viewing: 7 PM. Art Auction: 8 PM. East Martello Museum. 3501 S. Roosevelt Blvd.
• January 28 - 29, 2012 - ARTS - The 27th Key West Craft Show - Over 100 craft artists in Old Town Key West display art and crafts from wood, clay, fabric, metal and more! Whitehead Street & Caroline Street.  10-5 daily, FREE and open to the public. For more information, call 305-294-1243.
• January 29, 2012 - FOOD - 18th Annual Key West Master Chef Classic - Key West's talented chefs compete for top honors in this annual gourmet competition. Cost $55-$80, depending on beverage choice. Weston Resort & Marina, 245 Front Street. Call 305-294-9526, ext 25 for more information.
• January 29, 2012 - SAILING - 2012 Annual Schooner Wharf Bar Wreckers Cup Race Series - Sailing vessels of all sizes race to the reef - a nod to Key West's history of wrecking. In the early 19th century, when a vessel ran aground on the reef, sailboats would race from Key West to save the crew and claim the cargo. Just like then, first one to reach the reef wins bragging rights, trophies, and prizes. Race starts at 1pm in the Key West Harbor. Vessels interested in participating must attend the Captains' meeting held at 7pm, Saturday January 28. Awards Ceremony and Party is at 7pm Sunday - which includes BBQ and video of the race. Schooner Wharf Bar is at 202 William Street. For more information, call 305-292-3302
• January 30, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: James Gleick - Writer of many books on science and related subjects, including Genius: The Life and Science of Richard Feynman and Chaos: Making a New Science. The Information (2011), his most recent work has been praised in reviews in The New York Review of Books and The New York Times Book Review. 6 pm, Studios of Key West, 600 White Street. FREE.

February 2012

• February 4, 2012 - FUNDRAISER - Florida Keys 5th Annual Rock 'N' Roast - Some of the best Florida Keys musicians and food will be offered at this annual benefit for the Mari Immaculate School. Line-up includes: Howard Livingston and Mile Marker 24, Paul Cotton, Bubba System, Adrienne, Libby York, Caesar & the Cajun Band, Mary Immaculate Star of the Sea Children's Choir, Zach Seemiller, 40-Foot Sharpie Band, and Robert Albury. Food is prepared by Chef John Correa from Cafe Sole and includes: traditional Cuban roast pork dinner, roasted chicken, vegetable medley, homemade desserts, and refreshments. Huge silent auction and 50/50 raffle will be held during event. Cost: $22 for adults, $12 for teenagers, $5 for 6-12 year olds, and FREE for kids 5 and under. Event location: Mary Immaculate School Grounds, 700 Truman Avenue. Event time: 2pm - 9pm. For more information, call 305-294-1031.
• February 6, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Roberta Isleib - Clinical psychologist and author of eight mysteries, including the Cassie Burdette golf mystery series and the Rebecca Butterman advice column mysteries. Her books and stories have been nominated for Agatha, Anthony, and Macavity awards. She is the past president of Sisters in Crime National and her new mystery is set in Key West. 6 pm, Studios of Key West, 600 White Street. FREE.
• February 13, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: David Garrard Lowe - Cultural historian, popular lecturer, and author of the books Stanford White's New York; Beaux Arts New York; Chicago Interiors; Lost Chicago; and Art Deco New York, in addition to many essays and lectures on as diverse subjects as Mark Twain, the fate of New York architecture, Cole Porter and the French Riviera. 6 pm, Studios of Key West, 600 White Street. FREE.
• February 14, 2012 - BENEFIT - 29th Annual Valentine's Gala - Starring Master of Ceremonies Howard Livingston, music and dancing with Raven Cooper and Honey Mouth, a world-class dinner buffet, open bar, and the island’s largest and most anticipated annual silent auction. General admission $40 in advance, $50 at the door; limited VIP seating $90. All proceeds benefit Wesley House Family Services. 6:30 pm - 9:30 pm, on the grounds of the historic Curry Mansion Inn, 511 Caroline Street. For more information call 305-809-5000.
• February 17 - 18, 2012 - ARCHITECTURE - 51st Annual House and Garden Tour - Visit five Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information.
• February 18 - 19, 2012 - GARDEN - Gardenfest Key West - Balmy Key West is bursting with tropical plants and flowers that you'll find nowhere in the US, except Hawaii. Maybe you didn't know that Key West is in Hardiness Zone 11 (you gardeners out there understand). Miami is in Hardiness Zone 10. So enjoy one of the most unique plant shows - featuring orchids, banana trees, bamboo, and other warm-loving tropical & native species. Key West Tropical Forest & Botanical Garden, 5210 College Road, Stock Island. Call 305-296-1504 for more information.
• February 20, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Roberta Marks - Visual artist who works in many genres including sculpture, construction, oil painting and collage. Her work is in the collections of more than 25 institutions in the US, France, Switzerland and England including the New Mexico Museum of Art, the Smithsonian Institution and the Victoria and Albert Museum in London. 6 pm, Studios of Key West, 600 White Street. FREE.
• February 25 - 26, 2012 - ARTS - The 47th Annual Old Island Days Art Festival - Over 100 Artists in Old Town Key West show watercolors, oil, acrylics, sculpture, art jewelry and more on Whitehead & Caroline Streets.  10-5 daily, FREE and open to the public. For more information, call 305-294-1243.
• February 25, 2012 - ODDITY - 6th Annual Sword Swallowing Show at Ripley’s Believe It or Not! - Free sword swallowing demonstrations. Watch local legend Dale Pritchard, aka D.W. Blade Master, perform a FREE show at Ripley’s Key West. Pritchard has been wowing Key West crowds with his sword swallowing skills for 31 years. 2pm, Ripley's Believe It or Not, 180 Duval Street. For more information, call 305-293-9939.
• February 26 , 2012 - SAILING - 2012 Annual Schooner Wharf Bar Wreckers Cup Race Series - Sailing vessels of all sizes race to the reef - a nod to Key West's history of wrecking. In the early 19th century, when a vessel ran aground on the reef, sailboats would race from Key West to save the crew and claim the cargo. Just like then, first one to reach the reef wins bragging rights, trophies, and prizes. Race starts at 1pm in the Key West Harbor. Vessels interested in participating must attend the Captains' meeting held at 7pm, Saturday February 25. Awards Ceremony and Party is at 7pm Sunday - which includes BBQ and video of the race. Schooner Wharf Bar is at 202 William Street. For more information, call 305-292-3302
• February 27, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Les Standiford - South Florida author of several novels including Spill (1991); Deal to Die For (1995); Presidential Deal (1998); and Black Mountain (2000); and non-fiction books including The Last Train to Paradise: Henry Flagler and the Building of the Overseas Railroad to Key West (2002). His most recent book is Bringing Adam Home: The Abduction that Changed America (2011). 6 pm, Studios of Key West, 600 White Street. FREE.

March 2012

• March 3, 3012 - MUSIC - 12th Annual Open Air Art & Music Festival - Local artists and musicians present their art and music. Free event to attend, and a good opportunity to see some authentic Florida Keys creativity on display. 10am until midnight. Schooner Wharf Bar, 201 William Street. For more information, call 305-292-3302.
• March 5, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Paul Hendrickson - Former staff writer for the Washington Post and currently professor at the University of Pennsylvania, he is the author of Sons of Mississippi: A Story of Race and its Legacy (2003) and The Living and the Dead: Robert McNamara and Five Lives of a Lost War (1997) among other books. His new book is Hemingway’s Boat: Everything He Loved in Life, and Lost, 1934-1961. 6 pm, Studios of Key West, 600 White Street. FREE.
• March 10, 2012 - ECO - Mangrove Cleanup - Help marine life and improve nearshore water quality by attending this mangrove cleanup event. Sponsored by Reef Relief, the Key West non-profit organization dedicated to protecting our coral reef and seas. 9:30am - 1:00pm. Following cleanup will be a bar-b-que and music at 1:00pm - 3:30pm. Meet at Stock Island Village Marina, 7009 Shrimp Road, Stock Island. For more information and to RSVP, call 305-294-3100.
• March 12, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Lou Harris - Internationally known political pollster and pundit that has for many years offered standing-room-only audiences for his annual political summary and prognosis. He plans to do so again this year. 6 pm, Studios of Key West, 600 White Street. FREE.
• March 18, 2012 - ARTS - 22nd Annual AIDS Help Art Auction - Forty artists donate works to be auctioned off at the Casa Marina hotel, all for the benefit of AIDS Help. Preview the artwork beginning at 4:30 pm at the Casa Marina Resort at 1500 Reynolds Street. FREE to attend. Call 305-296-6196 for more information.
• March 19, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Joy Williams - The well-known author of fiction and nonfiction who has written novels (The Quick and the Dead, 2002, and State of Grace, 1990), short stories (Honored Guests, 2005) and travel literature (The Florida Keys, which has gone through many revised editions). 6 pm, Studios of Key West, 600 White Street. FREE.
• March 25 , 2012 - SAILING - 2012 Annual Schooner Wharf Bar Wreckers Cup Race Series - Sailing vessels of all sizes race to the reef - a nod to Key West's history of wrecking. In the early 19th century, when a vessel ran aground on the reef, sailboats would race from Key West to save the crew and claim the cargo. Just like then, first one to reach the reef wins bragging rights, trophies, and prizes. Race starts at 1pm in the Key West Harbor. Vessels interested in participating must attend the Captains' meeting held at 7pm, Saturday March 24. Awards Ceremony and Party is at 7pm Sunday - which includes BBQ and video of the race. Schooner Wharf Bar is at 202 William Street. For more information, call 305-292-3302
• March 26, 2012 - LITERATURE - Friends of the Key West Library Lecture Series: Arlo Haskell - The publisher of Sand Paper Press and media director of the Key West Literary Seminar. He is the author of Joker, a collection of poems, and currently at work on two historical projects: a transcription of Charles Olson’s previously-unpublished Key West Notebooks, which illuminate a seminal period of the influential poet’s life; and a pictorial history of Key West’s Jewish community from 1883 to the present. 6 pm, Studios of Key West, 600 White Street. FREE.
• March 31, 2012 - BENEFIT - Reef Relief's 25th Anniversary Party - Celebrating 25 years of dedication to improving our coral reef ecosystem. Beachside party with food provided by Salute restaurant and cash bar. Tickets cost $15 in advance and $20 at the door. Music by Howard Livingston and the Mile Marker 24 Band. 6pm-10pm. 1000 Atlantic Blvd, Key West (at Higgs Beach, just east of the Casa Marina Resort). For more information, call 305-294-3100.

April 2012

• April 17-21, 2012 - FISHING - World Sailfish Championship - This tournament has been red hot for the past couple years with dozens of sailfish caught and released each day. Big dollar prizes will be awarded, including $100,000 for tournament winner. Registration is on Tuesday from 1-4pm at Mallory Square. That night is the Captain's meeting, also in Mallory Square, followed by the kick-off party. Tournament fishing is on Wednesday, Thursday, and Saturday. Awards are presented on Saturday night. For more information, call 305-395-3474
• April 20, 2012 - FUNDRAISER - 2012 Relay for Life of the Lower Keys - Benefits the fight against cancer. Festive atmosphere this night, with survivor's lap, food and music. Thirty-seven teams of participants walk sponsored laps for 24-hours. So far, $45,000+ has been raised! This year's event offers opportunity to participate in a long-term study of cancer prevention. 5pm, Bayview Park (near Truman Ave and Eisenhower Drive).
• April 20-29, 2012 - LOCAL COLOR - 30th Annual Conch Independence Celebration - Celebration of Key West's brief secession from the United States. Event highlights include drag (queen) races on Duval Street, and the infamous bloody battle in Key West harbor where Conch Republic vessels toss stale cuban bread at Coast Guard vessels and each other in a mock secession. Kick-off party at the Schooner Wharf bar on Friday April 20th, 7pm. For more information call 305-296-0213.
• April 20, 2012 - LOCAL COLOR - Conch Republic Independence Celebration Kick-Off Party & Conch Shell Blowing Contest - Prizes are awarded for contestants ability to coax sound from a conch shell by blowing into it like a trumpet. 7pm, Schooner Wharf Bar, 202 William Street. FREE to attend.
• April 21, 2012 - LOCAL COLOR - Bourbon Street Pub Drag Races - Watch the ladies fire up their high heels and race down Duval Street in this one-of-a-kind event. 1pm - 5pm. 700 and 800 blocks of Duval Street.
• April 21, 2012 - MUSIC - Howard Livingston Band Concert - Carrying forward the trop-rock musical torch first illuminated by Mr. Buffett is the Florida Keys' own Howard Livingston Band, with its breezy and bouncy tunes, beach-loving lifestyle, and margarita blender made from a boat engine. Free concert at Turtle Kraals restaurant and bar. 231 Margaret Street, 5pm-10pm.
• April 21, 2012 - RUNNING - 31st Annual 7 Mile Bridge Run - One of the most unique running races in the world. 1500 runners from around the world race across the largest bridge of the Overseas Highway. According to organizers: "If you are interested  in running this race, send in a Self Addressed Stamped Envelope (business size) to request an  application. To make it fair, all requests for applications will be mailed out exactly at the  same time early in February 2011. Do not procrastinate sending in your request. Once the  applications are mailed out, we stop the requests. We accept up to the first 1500 correctly  filled out applications that are returned. The run fills up within two days after mailing so be  ready to get your application filled out correctly with fee enclosed and mailed back ASAP. You  may want to consider sending your prepaid self-addressed USPS overnight mail to receive your  application and return it the same way.  The fee for 2011 has not been determined yet. The 7-Mile Bridge Run is put on by THE MARATHON RUNNERS CLUB, a small group of individuals who  put this event together for local youth organizations. Send your request to: Marathon Runners Club, P.O. Box 500110, Marathon, FL 33050.  For more information, call (305) 395-7040.
• April 22, 2012 - LOCAL COLOR - 21st Annual Conch Cruiser Car Show - Painted cars and other unique vehicles are exhibited at the Schooner Wharf Bar. 12pm, Schooner Wharf Bar, 202 William Street. FREE to attend.
• April 23, 2012 - FOOD - 17th Annual Taste of Key West - For the benefit of AIDS Help, more than fifty Key West restaurants offer delicious tapas-sized portions along the Truman waterfront - each taste costing between $3 - $8. Always well attended, this lively event will have you bouncing from cuisine to cuisine, all the while enjoying the generous selection of fine wines available in a collectible wine glass. Car traffic is usually heavy - so come by bike or foot and breeze on past the cars lined up. Or take the Old Town Trolley, offering free transportation for the event, starting at 5:30 pm at the Pier House (1 Duval Street), with stops at the Westin, La Concha, corner of Simonton & South Street, and the Casa Marina Resort. Trolley runs every 30 minutes until last departure from Truman Waterfront Park at 9pm. Admission to event is FREE. Food tickets sold in $1 increments. For more information, call 305-296-6196.
• April 24, 2012 - LOCAL COLOR - Pet Stroll - Bring your beloved pet(s) to this event which shows off the island's four-legged community. Route follows the Green Street sidewalk from the Mel Fisher Museum to the Conch Republic Seafood Company. Register your pet at 5pm ($10). Pet parade begins at 6pm. Viewing is FREE.
• April 25, 2012 - LOCAL COLOR - Cultural Preservation Society Street Fair - Booths set up by local Florida Keys artists offering their artwork. Greene Street between Duval Street and Whitehead Street; Fitzpatrick Lane from Greene Street to Front Street. 10am - 5 pm.
• April 26, 2011 - LOCAL COLOR - Impromptu Parade on Duval Street - Part of the Conch Republic Independence Celebration, join and view the wacky hilarity of our colorful locals. Calls itself the "Worlds Longest Parade", as it goes from the Atlantic Ocean to the Gulf of Mexico. Parade starts at Duval Street and United Street at 7pm.
• April 27, 2012 - LOCAL COLOR - Bloody Battle in the Key West Harbor - Viewable only from the Key West Harbor (try the Sunset Pier at the Ocean Key House), vessels toss stale cuban bread at Coast Guard vessels and each other re-enacting the "secession" of Key West from the United States. (boat Captains who plan on participating must attend the mandatory Captain's meeting on April 24, 9pm, at the Schooner Wharf Bar, 202 William Street). Battle begins at 7pm. Get to your viewing position by 6pm.
• April 28, 2012 - ART - Conch Republic Craft Show & Food Festival - Street fair held on Greene Street offering local arts, street food, and party atmosphere. 10am-5pm. FREE to attend.
• April 28, 2012 - LOCAL COLOR - 29th Annual Bourbon Street Pub Bed Races - Creatively decorated beds, each equipped with wheels, are pushed by contestants in a race down Duval Street. Schedule is as follows: 2pm racers line up and bed inspection, 3pm parade of beds up Duval Street, and 3:30pm racing starts. Call 305-293-9800 to sign your team up for the event (deadline is April 23). Duval Street, between Fleming Street and Olivia Street.
• April 28, 2012 - RUNNING - Mary Immaculate Star of the Sea, Mariner's March 5K Run/Walk and 1/2 Mile Children's Fun Run - 8am. For more information, call 305-304-7444.
• April 29 , 2012 - SAILING - 2012 Annual Schooner Wharf Bar Wreckers Cup Race Series - Sailing vessels of all sizes race to the reef - a nod to Key West's history of wrecking. In the early 19th century, when a vessel ran aground on the reef, sailboats would race from Key West to save the crew and claim the cargo. Just like then, first one to reach the reef wins bragging rights, trophies, and prizes. Race starts at 1pm in the Key West Harbor. Vessels interested in participating must attend the Captains' meeting held at 7pm, Saturday April 28. Awards Ceremony and Party is at 7pm Sunday - which includes BBQ and video of the race. Schooner Wharf Bar is at 202 William Street. For more information, call 305-292-3302

May 2012

• May 2 - 6, 2012 - MUSIC - 17th Annual Key West Songwriter's Festival - Features more than one-hundred top songwriters performing at a variety of venues in Key West. Wednesday (May 2) will have a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street, 6pm-8pm. Saturday night (May 5) will be a free concert at the corner of Duval & Greene Streets 7pm.
• May 5, 2012 - CELEBRATION - Cinco de Mayo - Party at the Schooner Wharf bar in celebration of May 5 (aka Cinco de Mayo). Features taco eating contest, chili pepper eating contest, and prize for best mexican hat. Starts at 7 pm, 202 William Street. Call 305-292-3302 for more information.
• May 9, 2012 -  LOCAL COLOR - 28th Annual LaTeDa Redux Queen Mother Pageant - Drag queens compete for crown. 1125 Duval Street. 7pm to 10:30 pm.
• May 12, 2012 - SPORTS - Key West Paddleboard Classic - The paddleboard is a sort of over-sized, super-stable surfboard that lets you stand and paddle across the water. Combined with Key West's calm warm water, and you can see why paddleboarding is becoming popular on the island. This 12-mile race will certainly challenge participants as they circumnavigate the island of Key West. This year will also include a 4-mile race, who's course is yet to be determined. 12-mile race starts/ends at Smather's Beach. Call 305-797-1174 for more information.
• May 14, 2012 - LOCAL COLOR - 29th Annual Queen Mother Pageant - Drag queens compete in song and dance for title of Queen Mother. Benefits AIDS Help, and offers a cash bar and hors d'ouvers. LaTeDa, 1100 block of Duval Street, 6pm-11pm. For more information, call 305-294-8812.
• May 18-19, 2012 - HISTORY - Harry S. Truman Legacy Symposium - Senator Roy Blunt of Missouri will one of the speakers, along with scholars, discussing Truman's work with Foreign Aid. Key West Marriott Beach Conference Center. Cost is $125 per person. For more information, call 305-294-9911.
• May 19, 2012 - SPORTS - Keys 100 Ultra - 100 and 50 mile ultra marathons starting near Key Largo and in Marathon FL, finishing in Key West. Cost: $150 to $300 for individuals (depending on race length and time of registration), and $480 to $810 for teams (depending on race length and time of registration). For more information, call 954-439-2800.
• May 26, 2012 - FISHING - 11th Annual Yamaha Dolphin Masters Invitational - Dolphin fish, also known as Mahi-Mahi or Dorrado, is NOT the marine mammal with the same name. They look very different too. Dolphin fish are plentiful during summer offshore of Key West, and this tournament will reward the boat that catches the biggest combined weight of three fish. Costs $715 to enter. $12,500 in prizes. Call 305-296-7511  for more information.
• May 26, 2012 - MUSIC - Reggae Moonsplash - Four bands will perform on the beach at this mini music festival. Features Julian Marley & the Uprising (a 9-piece band founded by the son of reggae legend Bob Marley), the SPAM Allstars, Suenalo, and another act. Gates open at 6:30pm. Music is from 7pm-11:30pm. Tickets cost $22 in advance, $30 at the door - and can be purchased at Stick & Stein, Neptune Designs, and Southernmost Beach Cafe. Higgs beach is located just east of the Casa Marina Resort on the south side of the island (1000 Atlantic Blvd).
• May 27, 2012 - LOCAL COLOR - 21st Annual Schooner Wharf Minimal Regatta - Hysterical race of build-your-own boats using a minimum supply of materials, including: one sheet of plywood, two 2x4s, one pound of screws/fasteners, and one roll of duct tape. Prizes awarded for fastest team, most creative design, sinker award, sportsmanship award, best costumed, and best paint job. Vessel inspection at 12pm, Schooner Wharf Bar, 202 William Street. For more information, call 305-292-3302. 
• May 28, 2012 - FUNDRAISER - 35th Annual Survivors Party - Benefiting the Sister Season Fund, dedicated to helping hospitality workers injured through no fault of their own, this fundraiser will feature live music from the Doefuls, bar-b-que, picnic, silent auction, and 50/50 raffle. Tickets cost $20 and include food. Cash bar available. 4pm-8pm at the Southernmost Beach Cafe, 1405 Duval Street.

June 2012

• June 1 - 3, 2012 - MUSIC - Verizon Summer Music Festival - Benefits Bahama Village Music Program. Features Tito Puente Jr & his band, plus four other acts. Festival hours are: June 1: 4pm-11pm; June 2: Noon-11pm; June 3: Noon-11pm. Mallory Square. FREE event.
• June 6 - 10, 2012 - GAY/LESBIAN - Pridefest Key West 2012: Key West Pride - Event honoring the diversity, openness and freedom in the city that is consistently recognized as one of the world's top gay land lesbian vacation destinations. Includes a mix of dance and cocktail parties, contests, shows, forums, activities on the water, tours, street fair and the Pride Parade along Duval Street. For more information, call (305) 292-3223.
• June 6, 2012 - SPORTS - FKCC Swim Around Key West - Swimmers race around the island of Key West, a twelve-and-half mile course, competing for awards. Cost is $100 per person, $160 per two-person relay, $240 per three-person relay, $320 for four-person relay, $400 for five-person relay, and $480 for six-person relay. Race starts at 7am. For more information, call 305-809-3562.
• June 9 - 10, 2012 - GAY/LESBIAN - Key West Pride Celebration - Features numerous events and parade on Duval Street, starting with a street fair on Saturday on the 700-800 block of Duval Street from 10am-7pm. Parade is Sunday from 5pm-7pm. Parade route starts in Truman Annex, then left on Whitehead Street, right on Duval Street, and ending at 1100 block of Duval Street. Expect food, drink, and lively celebration. FREE to attend.
• June 9, 2012 - FISHING - Florida Keys Sanctuary Classic Fishing Tournament - Sanctuary Classic Fishing and Photo Contest featuring Kids Hooked on Fishing Kick Off Event. Kids bring your parents and learn to fish with Hooked on Fishing. National Marine Sanctuary Eco-Discovery Center (by Fort Zachary Taylor State Park entrance, at the end of Southard Street). Begins at 8am and lasts 4 hours. For more information, call 805 895 3000. FREE to participate.
• June 22 - 24, 2012 - FISHING - Key West Gator Club Dolphin Derby - Fishing tournament focusing on Key West's favorite summertime offshore species: dolphin fish ( a.k.a. mahi-mahi or dorado). For more information, call 305-304-7674.
• June 23, 2012 - SPORTS - 36th Annual Swim Around Key West - Swimming race circumnavigating the island of Key West, a 12.5 mile course. Each swimmer must have a support vessel (usually a kayak) stay with them. Race begins and ends on Smathers Beach. For more information, call 305-394-5292.
• June 23, 2012 - ARTS - The 6th Annual Midsummer’s Night Dream and Spectacle - Centennial Bank presents the most magical night of summer – the Midsummer’s Night Dream and Spectacle – a night of artistic expression, music, feasting, dancing, singing, and theatrical antics celebrating the art and artists of the Keys. Co-produced by Michael Shields’ Java Studios and The Key West Tropical Forest and Botanical Garden, the event benefits the Tropical Forest and Botanical Garden and Art Behind Bars. Admission is $10 for adults; children under age 12 and Centennial Bank Customers are admitted free. 5pm-11pm, 5210 Collage Road. For more information, call 305-394-3804.

July 2012

• July 4, 2012 - INDEPENDENCE DAY - Key West Fireworks - Dazzling fireworks show is launched from the White Street pier on the south side of the island of Key West. Begins shortly after sunset. Popular tradition is to view the fireworks from the water aboard a boat. More information and reservations for boat options at Key West July 4th Fireworks Cruises.
• July 4, 2012 - INDEPENDENCE DAY - 4th Annual Fourth of July Harbor Walk Bar Stroll - Bar hopping in honor the July 4th, participants visit waterfront bars while dressed in red, white, and blue. $25 includes comemorative t-shirt, drinks, and food. 2pm, begins at the Ocean Key House pier, 0 Duval Street. For more information, call 305-766-0239.
• July 6, 2012 - MUSIC - Reggae Concert on Sunset Pier - Featuring The Original Wailers (from Bob Marley & the Wailers), Yellowman and Sagatarius Band, and DJ. 7pm-11pm, 0 Duval Street (Ocean Key House's Sunset Pier). Tickets are $25 in advance and available at Ocean Key House. Call 305-296-6353 for more information.
• July 12, 2012 - HISTORY - Kick-Off Party for Mel Fisher Days - Come celebrate the day 26 years ago when Mel’s crews found $400 million in shipwrecked gold, silver and emeralds that had been sitting on the ocean floor for more than 300 years. Throughout the night, more than $5,000 in Spanish Treasure Coins, Emeralds and Cash will be given away and live music is by C. W. Colt, the “Caribbean Country Blues Master”. All monies raised benefit the non-profit Mel Fisher Maritime Heritage Society. As Mel always said of Schooner Wharf Bar, “This place is a Treasure,” so come enjoy the evening at Mel’s favorite watering hole with the Fisher family, and treasure your own memories.  Schooner Wharf Bar, 202 William Street (Lazy Way Lane). Starts at 5pm.
• July 15 - 18, 2012 - FISHING - Del Brown Permit Tournament - Considered amongst anglers to be the hardest and most rewarding fish to catch in shallow water on fly, this tournament is named after the early innovator of the sport Del Brown, who showed that you can catch a permit on fly - more than once in a lifetime. Really, it is a feat of a lifetime, but if you have the skills, pattern, and luck, then you just may have a chance. Call 305-942-0428 for more information.
• July 18 - 21, 2012 - FISHING - Drambuie Key West Marlin Fishing Tournament - Coinciding with the Hemingway Days celebration, this fishing tournament has anglers competing for the king of all gamefish - the marlin. Large cash prizes for largest fish, including marlin, dolphin fish (mahi-mahi), wahoo, and sailfish. Cost is $1500 per vessel for early registration, or $1800 for late registration. Additional fees for fun fish, extra angler, and extra banquet tickets. For more information, call 305-292-2710.
• July 19 - 21, 2012 - HEMINGWAY - 32nd Annual Hemingway Look-Alike Contest - Held at Sloppy Joe's bar, one of Hemingway's favorite watering holes, this competition features dozens of Hemingway look alikes competing for prizes and bragging rights. Costs $35 to register. FREE to watch. 6:30pm at 201 Duval Street. For more information, call 305-294-5717.
• July 24, 2012 - MUSIC - Symphony of the Americas - Impromptu Classical Concerts again hosts a 5-star concert at 2-star prices when Symphony of the Americas brings its 2012 Summerfest performance, with the Mission Chamber Orchestra, to Key West. 8p.m, St. Paul’s Church, 401 Duval Street. $20 tickets are available at church door. All students free.
• July 25 - 26, 2012 -- FISHING - Lobster Mini-Sport Season - Two-day event draws hundreds of sometimes frenzied recreational boaters in search of Florida lobster. Many rules apply, including: Bag limit: 6 per person per day for Monroe County. Possession limit - on the water: equal to the daily bag limit. Possession limit - off the water: equal to the daily bag limit on the first day, and double the daily bag limit on the second day.  Possession limits are enforced on and off the water. Minimum size limit: must be larger than 3" carapace, measured in the water.  A reminder that possession and use of a measuring device is required at all times, and night diving is prohibited in Monroe County (only during the sport season). Florida Saltwater Fishing License plus lobster endorsement/stamp required. Please respect other boaters, stay away from shorelines, ecological reserves, no-take zones, and canals, use a dive flag, and do no harm to the sensitive coral and eco-system. Call Florida Fish & Wildlife (FWC) at 305-289-2320 for more information.

August 2012

• August 5, 2012 - LOCAL COLOR - 19th Annual Schooner Wharf Battle of the Bars - The staff of local watering holes compete for top honors in drink-making competition. This hilarious all-in-fun relay race has raised almost a quarter-million dollars for charity throughout the years. This year's entry fees and "bribes" will be donated to Womankind and Boys and Girls Club. Besides the fastest teams, there will also be trophies and prizes for the Most Outrageous Team Costume and Deepest Pockets. Schooner Wharf Bar, 202 William Street. Begins at 12:30 pm. To register your team, call 305-292-3302 by July 26. Entry fee is $35.
• August 10 - 12, 2012 - SEAFOOD - Key West Lobster Fest - Everyone will be partying on Duval Street, except the lobsters. Marking the official opening of lobster season, this crustacean-focused event features street fairs, live music, and arts & crafts. Street fair with free live concert on Saturday, noon-11pm, lower Duval Street.
• August 16 - 19, 2012 - GAY - Tropical Heat Key West - Four days of all-male parties and gatherings at the island's gay guesthouses. For more information, call 305-294-4603.
• August 30 - September 3, 2012 - PARTY - Key West Brew Fest 2012 - Labor-day weekend event featuring more than 60 different beers - including many award-winning microbrews. For more information, call 1-800-354-4455.

September 2012

• August 30 - September 3, 2012 - PARTY - Key West Brew Fest 2012 - Labor-day weekend event featuring more than 60 different beers - including many award-winning microbrews. For more information, call 1-800-354-4455.
• September 4 - 9, 2012 - GAY/LESBIAN - Womenfest Key West - Lesbians and friends converge on Key West for a week of activities, including late night dancing, pool parties, comedy shows, sunset sails, competitive bull riding, and lots of music. Call 305-294-4603 for more information.
• September 7 - 9, 2012 - FISHING -  S.L.A.M. Celebrity Tournament - In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted "flats grand slam." The event raises funds for the fight against cystic fibrosis. For more information, call 305-664-2002.
• September 13 - 16, 2012 - MOTORCYCLE - 40th Annual Key West Poker Run - Over 10,000 motorcycles ride to Key West on one of the most scenic and unique roads in North America, the Overseas Highway, while collecting poker cards. Prizes awarded for the best hand. Any make of motorcycle, car, or truck is welcome. It doesn't matter what you ride or drive. For more information, call 305-235-4023. (A couple blocks on lower Duval Street will likely be closed to traffic while lined with sparkling chrome and black leather).

October 2012

• October 21, 2012 - PARTY - 32nd Annual Goombay Fest 2012 - This street party brings out all the locals to Bahama Village and features street fair cuisine (conch ceviche made fresh is popular), vendors selling a variety of wares, and live music at the bottom of Petronia. Don't miss the Robert Albury Band at 9:30 pm - offering the best of R&B - and the party inside Blue Heaven. This is a family friendly event and NOT the time to be wearing body paint or showing too much skin. 10am - 11pm. Petronia Street starting at Duval Street. FREE to attend.
• October 22, 2012 - PARTY - 32nd Annual Goombay Fest 2012 - The party continues as Petronia Street is packed with people browsing the merchandise for sale, eating the street-fair cuisine, and dancing to the music. Don't miss the Junkanoo "rush" at 5:30 pm, followed by the Junkanoo stage show is at 6:00pm. More live music on the street and in Blue Heaven. This is a family friendly event and NOT the time to be wearing body paint or showing too much skin. 10am - 11pm. Petronia Street starting at Duval Street. FREE to attend.
• October 19 - 28, 2012 - FANTASY FEST - Fantasy Fest 2012 - Weeklong celebration and Key West's biggest party of the year - with many adult-only events. This year's theme is "A-Conch-Alypse".
  • October 21, 2012 -FANTASY FEST EVENT- 2nd Annual Wet and Wild Blue Pool Party - Benefits AIDS Help. Poolside party with a beach/water theme and featuring live music by Howard Livingston and the Mile Marker 24 Band. 3pm-6pm at Sheraton Suites, 2001 South Roosevelt Boulevard. Cost is $10 and includes snacks, cash bar, and raffle. Call 305-292-4360 for tickets.
  • October 22, 2012 -FANTASY FEST EVENT- Pinking of You - Decorated Bra Auction - Features local artists decorating bras to be auctioned off to benefit Womankind. 6pm at the Westin Resort at 245 Front Street.
  • October 23, 2012 -FANTASY FEST EVENT- Official Fantasy Fest Poster Signing Party - Meet this year's poster artist and buy a signed copy of this collector's item. Crowne Plaza La Concha Hotel, 430 Duval St, 4:30pm.
  • October 23, 2012 - FANTASY FEST EVENT - 30th Annual Headdress Ball - Dazzling headdresses, created over many months, are worn and displayed in this awe inspiring event. HUGE works of art, each more inventive and imaginative then the previous. Southernmost Hotel on the Beach, 508 South Street, Seating begins 7 pm, 8 pm. Buy tickets early as this event sells out. Call 305-294-4603 for tickets.
  • October 23, 2012 - FANTASY FEST EVENT - Finnegan's Wake Green Party - Celebrate all things green at Key West's most authentic Irish pub. 7pm, 320 Grinnell Street. Entry is free - so long as you wear green.
  • October 23, 2012 - FANTASY FEST EVENT - Captain Tony's Party in Plaid - Bar party with attendants dressed in plaid. Offers live music, rum specials, and lively atmosphere. 428 Greene Street. Free event.
  • October 23, 2012 - FANTASY FEST EVENT - Chippendale Tighty Whitey Party - Party held at local strip club featuring male dancers from Chippendale and celebrity impersonator. Attendants are encouraged to wear white underwear. 8pm at 1029 Truman Avenue (Bare Assets). Call 305-304-1188 for more information.
  • October 23, 2012 - FANTASY FEST EVENT - Wild, Wild Key West Party - Cowboy and indian themed party, with prizes for best costume. Features bull riding competition, music, and drinks. 10pm at Cowboy Bills, 610.5 Duval Street. Call 305-295-8219 for more information.
  • October 24, 2012 - FANTASY FEST EVENT - Pet Masquerade & Parade - Hilarious event that features pets and their owners in costume. Dogs, cats, snakes, ducks, and even a lobster showed up at last year's event. Event is FREE to watch. Registration is at 4:30 pm, contest starts at 5:30 pm, Casa Marina Resort, 1500 Reynolds St. Call 305-304-1026 for more information.
  • October 24, 2012 - FANTASY FEST EVENT - Redneck Party - Costume contest and party with a "redneck" theme. 7pm at Lazy Gecko bar, 200 Duval Street.
  • October 24, 2012 - FANTASY FEST EVENT - Homemade Bikini Contest - Competition featuring homemade bikinis, from coconut shells to cocktail napkins, and nearly anything else you can think up. Costs $20 to compete. Begins at 7pm at Sunset Pier, 0 Duval Street. Free to attend.
  • October 24, 2012 - FANTASY FEST EVENT - Wharfstock - Put on your best flower child, hippie inspired, psychedelic era costume and party down at the Schooner Wharf Bar. Features live music, drinks, and costume contest. Begins at 7pm at Schooner Wharf Bar, 202 William Street. Free to attend.
  • October 24, 2012 - FANTASY FEST EVENT - Wicked Hot Tuna Contest - Sexy costume contest, begins at 9pm at Smokin Tuna, 4 Charles Street. Call 305-517-6350 for more information.
  • October 24, 2012 - FANTASY FEST EVENT - Celebrity Look Alike Contest - Plenty of double takes as contestants compete for prizes. Crowne Plaza La Concha Hotel, 430 Duval St, Contestant sign up 8 pm; FREE to watch; FREE to enter.
  • October 24, 2012 - FANTASY FEST EVENT - Dungeon of Dark Secrets and Fetishes - Leather & fetish party. - 9 pm at 801 Duval Street, 801 Bourbon Bar. Call (305)294-4737 for more information.
  • October 24, 2012 - FANTASY FEST EVENT - Fogarty's Red Party - Wear red & party on down at this Duval Street bar. DJ dancing and costume contest. 227 Duval Street - 9pm. $10 per person. Call 305-294-7525 for more information.
  • October 24, 2012 - FANTASY FEST EVENT - Swing & Skin Freak Fest - Features Kristy Morgan (from Playboy), gets down and dirty at local strip club. Attendants are encouraged to join in the freakiness. 1029 Truman Ave (Bare Assets). Begins at 10pm. Call 305-304-1188 for more information.
  • October 25, 2012 - FANTASY FEST EVENT - Dante's 4rd Annual Halos & Horns Pool Party & Wet T Shirt Contest - Features prizes, live music, free body painting, and naughty-themed antics. 12pm - 6pm, 951 Caroline Street.
  • October 25, 2012 - FANTASY FEST EVENT - Blackout Glow Party - Black-light party featuring sexy costume contest, bar-top dancing, and more. Contestants sign up at 8pm, contest begins at 10pm. 218 Duval Street at the new Coyote Ugly bar. Call 305-294-8459 for more information.
  • October 25, 2012 - FANTASY FEST EVENT - Pretenders in Paradise - Like no other costume contest, ENOURMOUS costume creations fill the stage for big dollar prizes. 1 Duval Street, Pier House Resort & Caribbean Spa, 8pm. Call 305-296-4300 for more information and tickets.
  • October 25, 2012 - FANTASY FEST EVENT - Sloppy Joe's 28th Annual Toga Party - Dress in a toga (extra points for incorporating this year's Fantasy Fest theme: “A-Conch-Alypse.”) Contest at 9:30 pm. If you want to compete, free registration is at 8pm. 201 Duval St.
  • October 25, 2012 - FANTASY FEST EVENT - Exposed at Bourbon Street Pub Adult Entertainment Complex - Clothing optional party at Bourbon Street Pub. Features foam party, dancing, male and female exotic dancers, all in an outdoor setting. Begins at 9pm at 724 Duval Street. Call 305-293-9800 for more information.
  • October 25, 2012 - FANTASY FEST EVENT - 6th Annual Cowboy Bill's Wet T-Shirt Contest - Contestants compete for prizes in this eye-popping event. 610 1/2 Duval St.; 10 pm; Call 305-295-8219 for tickets and information.
  • October 25, 2012 - FANTASY FEST EVENT - Monsters Ball - Swim into a sea of marine life at Key West's famous Green Parrot Bar. Features live music, costume contest, and all night partying. Green Parrot Bar; 601 Whitehead St.; 305-294-6133; 10 pm; FREE
  • October 25, 2012 - FANTASY FEST EVENT - Pajama & Lingerie Party - Offers live music and costume contest. Purchase tickets early - event sells out. 10pm at Mangoes, 700 Duval Street, call 305-304-1188 for more information.
  • October 26, 2012 - FANTASY FEST EVENT - Hair of the Hog Leather and Lace Party - Costume contest held over "breakfast" at the Hog's Breath Saloon. Begins at 10am. 400 Front Street. Call 305-296-4222 for more information.
  • October 26, 2012 - FANTASY FEST EVENT - Masquerade March - Wander through Key West's quaint Old Town historic district with hundreds of other costumed participants. Beverage breaks along the way keep the merriment flowing. Begins at Francis Street & Key West Cemetery at 5pm. FREE.
  • October 26, 2012 - FANTASY FEST EVENT - Fantasy Fest Street Fair - From noon to 10pm, Duval Street is closed to traffic as partiers and vendors pack Key West's most famous street. Many are in costume from the Masquerade March. Duval Street.
  • October 26, 2012 - FANTASY FEST EVENT - Living Art Airbrush Expo - The wildest and wackiest in body paint is put on display at this popular and sexy event. Contestants compete for $1500 in prizes while enjoying live entertainment and drinks. 9pm, Ocean Key House, 0 Duval Street. Call 305-295-7045 for more information.
  • October 26, 2012 - FANTASY FEST EVENT - Rum Barrel's 6th Annual Pirate Bash - Dress like a pirate and shake your booty. Prepare to aaaaargh all night. 9pm, Pirate Soul Bar & Restaurant, 528 Front Street.
  • October 26, 2012 - FANTASY FEST EVENT - Fetish & Fantasy Party - Clothing optional Adults only/Men only party features costume contest & "special" dungeon. Island House, 1129 Fleming St. 10:00 p.m. to 4:00 a.m.; call 305-294-6284 for more information.
  • October 26, 2012 - FANTASY FEST EVENT - Pimp & Ho Party - Featuring mega-porn star Ron Jeremy. Costume contest and dancing. Event sells out - purchase tickets early. 10 pm at Redfish Bluefish, 407 Front Street, call 305-304-1188 for more information.
  • October 27, 2012 - FANTASY FEST EVENT - Duval Street Promenade - Show off your costume on Duval Street. 12:00 pm - 10:30 pm. FREE event.
  • October 27, 2012 - FANTASY FEST EVENT - Epidermal Arts & Torso Tapestries - Tattoo and body paint competition features unique and varied works of body art. Green Parrot Bar; 601 Whitehead St. 2 pm; Call 294-6133 for more information. FREE event.
  • October 27, 2012 - FANTASY FEST EVENT - Captain Morgan Fantasy Fest Parade - Key West's biggest party of the year is on Duval Street as creative floats, outrageous costumes, and beads beads beads are abundant. Parade starts on Southard Street in Truman Annex, turns left onto Whitehead Street, right on Front Street, and right onto Duval Street where up to 100,000 attendants will be cheering and begging for beads. 7pm. FREE
  • October 27, 2012 - FANTASY FEST EVENT - Children's Day - A family event featuring food, games, arts and crafts and a costume contest for children. Bayview Park at Truman Ave. and Eisenhower Dr. 12:00pm - 5 pm.Call 305-292-8912 for more information.
  • October 27, 2012 - FANTASY FEST EVENT - The Fat Lady Sings Tea Dance - Last official event of Fantasy Fest, 4pm - 8pm. LaTeDa, 1125 Duval Street, call (305) 296-6706 for more information. $5 per person.

November 2012

• November 1 - 4, 2012 - MUSIC - 20th Annual Meeting of the Minds 2011: Don't Stop the Carnival - Parrothead convention nirvana benefiting charity. Many events are member only. Live shows include members of Jimmy Buffett's band. Last year Mr. Buffett himself actually showed up and played a free concert on Duval Street! Check out the Margaritaville Street Fest on Friday November 4, from 1pm - 6pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public.
• November 4 - 11, 2012 - SPORTS - 31st Annual Key West World Championship - Considered the pinnacle of offshore powerboat racing. Top powerboat & superboat offshore racers compete for title of World Champion. Spectators line the Key West harbor to see the 100+ mph action. Good viewing from Fort Zachary Taylor State Park at the end of Southard Street. For more information, call 305-296-6166.
• November 17, 2012 - MUSIC - Reggae Moon Splash - Beachside reggae concert featuring the great Pato Banton and one of the Marley sons. Bar-b-que to benefit Womankind will be 5-8 pm. Concert is until 10pm. Higgs Beach.
• November 26 - December 2, 2012 - FESTIVITIES - Pirates in Paradise Festival - The organizers of this event have announced that there will not be a pirate festival this year, and that Pirates in Paradise 2012 is CANCELLED.
• November 30 - December 1, 2012 - SPORTS - 3rd Annual Key West Triathlon - After the huge sold-out success of its first year, the athletes enthusiastically return to Key West to swim, run, and bike among Key West's ideal scenery and conditions. More than 500 competitors are expected. For more information, call 305-394-3469.
• November 30 - December 8, 2012 - PIRATES - Fort Taylor Pyrate Invasion - Pirate re-enactors create an atmosphere from earlier maritime history. Features musicians, crafts, and demonstrations. Admission is FREE with your paid admission to Fort Zachary Taylor State Park. Enter at Truman Waterfront, at the end of Southart Street. 10am - 5pm.

December 2012

• November 26 - December 2, 2012 - FESTIVITIES - Pirates in Paradise Festival - Arrrrrrrrg! Nine days of pure piratical escapades celebrating Key West's rich & colorful maritime heritage. Call 305-296-9694 for more information.
• November 30 - December 1, 2012 - SPORTS - 3rd Annual Key West Triathlon - After the huge sold-out success of its first year, the athletes enthusiastically return to Key West to swim, run, and bike among Key West's ideal scenery and conditions. More than 500 competitors are expected. For more information, call 305-394-3469.
• December 1, 2012 - ARTS - Sculpture Key West 2012 - Sculptures are installed at three locations on the island - providing visitors a creative, unique, and thought-provoking display of contemporary art. The exhibits are well worth checking out. Visit West Martello Tower, Fort Zachary Taylor State Park, and the Key West Tropical Forest & Botanical Garden. For more information, call 305-295-2800.
• December 8, 2012 - HOLIDAY - Key West Holiday Parade - A favorite of local children, the Key West Holiday Parade features homespun floats and costumed participants tossing candy to the cheering crowd. Parade route begins at Truman and White Street, continues down Truman to Duval Street, and turns right onto Duval Street until Eaton Street. FREE to attend. This very family-friendly event begins at 7pm.
• December 15, 2012 - HOLIDAYS - Lighted Boat Parade - Vessels of every size and shape deck their hulls and light up the night with their creativity and originality to the delight of locals and visitors alike. Santa Claus has been spotted at the helm, ditching his sleigh for a center console or sailboat with mistletoe hanging from the mast. His first mates have included gingerbread men and the Grinch. Other times, dolphins have replaced cold-weather reindeer, ushering in Santa’s sleigh packed with lighted presents. Festivities start at 6 p.m. with the Gerald Adams Steel Your Heart Band, and the parade begins at 8 p.m. Boats will come into the Key West Bight and pass in front of the judges' stand at Schooner Wharf. Live music all evening with yuletide favorites, plus a traditional ham dinner served from our galley. Captains' meeting is Friday, December 14. Awards ceremony is Sunday, December 16. To register your boat or for more information, please call (305) 292-3302.
• December 20, 2012 - ARTS - Peace By Piece - Opening reception for art show of collage paintings by Gretchen Mills. This local artist and yoga instructor displays her stunning, fresh, original, and creative works of art which combines collage with painting. 6pm-9pm at 929a Truman Avenue (the Key West Pottery studio and gallery). For more information, call 305-900-8303.
• December 27 - 29, 2012 - ARCHITECTURE - 53rd Annual House and Garden Tour - Visit five Key West homes and tropical gardens. 4pm - 8pm. Tickets are $25. Call 305-294-9501 for more information.
  
• December 31, 2012 - CELEBRATION - Key West New Year's Eve - Celebrations include the lowering of the Conch Shell over Sloppy Joe's on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, and the lowering of the "pirate wench" from the mast of a schooner in the Historic Seaport.