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 and we'll quickly add it.

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

Here is the upcoming calendar of events:

2010 Key West Calendar of Events

January 2010:

• December 2-January 2, 2010 - THEATER - A Christmas Survival Guide- Musical by James Hindman and Ray Roderick, Musical Arrangement by John Glaudin Directed By Joy Hawkins, Red Barn Theatre - 319 Duval Street, Rear, Key West. Box Office: 305-296-9911
• January 7 - 10, 2010 - LITERARY - 28th Annual Key West Literary Seminar - This year's topic is “Clearing The Sill of the World,” a celebration of 60 years of American poetry in honor of Richard Wilbur. For more information, call (888) 293-9291.
• January 8, 2010 - THEATER - The Suitors - by Jean Racine translated, by Richard Wilbur, Directed By Joy Hawkins - Red Barn Theatre, 319 Duval Street, Rear, Key West. Box Office: 305-296-9911
• January 9 to April 24 - ART - Sculpture Key West 2010 - Outdoor sculpture exhibition at Fort Zachary Taylor State Park and West Martello Tower. Cutting edge sculptures made by artists from around the world. For more information, call 305-295-3800.
  
• January 13 & 14, 2010 - MUSIC - Key West Symphony Master Concerts Series II - Israeli Violin/Composer, Ittai Shapiro and Jin Hi Kim, Korean Drums/Composer join the Key West Symphony performing their own Compositions. Tennessee Williams Theater, 5901 College Rd, Stock Island. 8 pm. For more information and tickets, call 305-296-1520.
  
• January 13 - February 13, 2010 - THEATER -Women Who Steal by Carter W. Lewis. Director Rebecca Tomlinson - Red Barn Theatre, 319 Duval Street, Rear, Key West. Box office: 305-296-9911
• January 15-16, 2010 -- ARCHITECTURE- House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25, and include transportation on a Conch Tour Train.  Call 305-294-9501 for more information.
• January 16, 2010 - FOOD - 5th Annual Florida Keys Seafood Festival - Growing more popular each year, this festival celebrates Key West's abundant fresh seafood with music & beverages served up by many of the Florida Keys commercial fisherman and families. Crab, lobster, ceviche, conch chowder, and other local cuisine is served up in a picnic setting. Entrance is free. 11 a.m. - 9 p.m. Bayview Park at Truman Avenue and Eisenhower Drive, Key West. For more information, call 305-872-9026.
• January 16 - April 16, 2010 - ART - Sculpture Key West 2010- Each year artists from Key West and beyond install a thoughtful, inventive, and often whimsical collection of outdoor sculpture. Be sure to visit all three locations: Key West Garden Club at West Martello Tower (southern end of White Street), Key West Tropical Forest & Botanical Garden (5210 College Road, Stock Island), and Fort Zachary Taylor Historic State Park (at the end of Southard Street). For more information, call 305-295-3800.
• January 16, 2010 - ART - Sculpture Key West 2010 Opening & Reception - 3 pm - 6 pm: Free Admission to Fort Zachary Taylor, then the 5:30 - 7:30 pm: Opening Reception at West Martello (southern end of White Street).
  
• January 16, 2010 - MUSIC - Key West Symphony Master Concerts Series II - Tennessee Williams Theater, 5901 College Rd, Stock Island, 8pm. For more information and tickets, call 305-296-1520.
• January 18 - 22, 2010 - SAILING - Premier Racing Presents: Key West 2010 - Known locally in Key West as "race week", this world class sailing competition hosts nearly 300 racing yachts compete for class championships in this international midwinter sailboat regatta. Call (781) 639-9545 for more information.
• January 22 -24, 2010 - FISHING - Hog's Breath King Mackerel Tournament - Using the fastest boats in competitive saltwater fishing, highly competitive anglers seek the largest and most king mackerel for cash prizes. For more information, call (305) 296-0364.
• January 23, 2010 - ART - Anne McKee Artists Fund Auction - Nearly 100 artists are to exhibit and auction their work to raise money for the fund that provides project-based grants to Keys artists. Artwork includes original paintings, sculpture, photography, fiber art, ceramics and more. East Martello Museum, 3501 S. Roosevelt Blvd, Key West.
  
• January 24 - February 9, 2010 - THEATER - Speed the Plow by David Mamet - Directed By Carole MacCartee, Red Barn Theatre, 319 Duval Street, Rear, Key West. Box office: 305-296-9911
• January 28 - 31, 2010 - MUSIC - 1st Annual Key West Dulcimer Fest - 15 of the best performers of mountain dulcimer and hammered dulcimer will be presenting concerts and teaching workshops to registrants and to the general public.  Registrations are $95 and include all concerts and classes.  Vendors will be on hand with instruments and beginner lessons are available.  Contact Bing Futch at (407) 342-1447 for more info.
• January 29 & 30, 2010 - MUSIC - Locos Por Juana Live - Grammy nominated Locos Por Juana performs live at The Green Parrot Bar. A show not to be missed. Playing new songs from the up and coming Album. 10pm, 601 Whitehead Street. FREE.
  
• January 30 - 31, 2010 - ART - 25th Annual Key West Craft Show - Open air art market and judged show offering an amazing variety of work, including sculpture, paintings, craft, and folk art. Whitehead Street and Caroline Streets, Key West. For more information, call (305) 294-1241.
• January 31, 2010 - SPORTS - 12th Annual Key West Half Marathon - 7:00 AM. Registration costs $45 by Jan. 20, 2009, $50 thereafter. Dante's Restaurant, 951 Caroline Street (The registration booth will be set up at Lands End Marina on Saturday January 24 from 5 PM till 8 PM. Race packets can be picked up at this time. Registration booth will also be open race day starting at 6 am.) Awards ceremony with great prizes distributed will follow the race. Awards will given to First thru third Male/Female three deep from 14 & Under to 70 & Over. First Place Overall Male/Female and First & Second Masters and a Military Division.
  

February 2010

• February every day - ART - Sculpture Key West 2010- Each year artists from Key West and beyond install a thoughtful, inventive, and often whimsical collection of outdoor sculpture. Be sure to visit all three locations: Key West Garden Club at West Martello Tower (southern end of White Street), Key West Tropical Forest & Botanical Garden (5210 College Road, Stock Island), and Fort Zachary Taylor Historic State Park (at the end of Southard Street). For more information, call 305-295-3800.
• February 7 - 15, 2010 - SPORTS - 19th Annual Kelly McGillis Classic - Women's flag football teams from all over the world to compete in the International Women's Flag Football Association largest tournament. Call 888-GO-IWFFA for more information.
• Monday, February 8-10, 2010 - MUSIC - Si Senorita - Dance under the stars and over the ocean to the groovy sounds of Si Senorita. Free concert presented by Sunset Pier Key West Concert Series. 0 Duval Street - 6pm to 9pm - FREE. For more information call 305-295-7047.
• February 12-13, 2010 -- ARCHITECTURE - House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information.
• Friday, February 19, 2010 - MUSIC - Stephen Marley - The son of roots-Reggae legend Bob Marley returns to Key West to play his grammy award winning music. Outdoor concert on the sunset pier overlooks the Key West harbor. $25 in advance/$35 at the door (show sold out last year). Doors open at 8pm. 0 Duval Street. Call 305-295-7047 for more information.
• February 19 - 21 - 2010 - GARDENING - Gardenfest Key West - South Florida's top nurseries will show bromeliads, orchids, fruit trees, palms, tropical flowers and natives for the Botanical Gardens' annual plant sale! Attend landscaping workshops, learn how to build your own native garden, browse through garden supplies booths, and arts and crafts. Docent tours will be offered. Plant sale is free and open to the public. Gates open 9 a.m. - Call 305-296-1504 for more information.
• February 19 - 22, 2010 - WRITING - Key West Travel Writing Workshop - Learn the secrets of travel writing from Bob Fisher, a Frommers writer and contributing editor.  The course concentrates on how to shape your travel story into something that editors would consider buying. The course includes instruction on different types of travel writing, kinds of outlets, methods of research, determining the market, self-publishing, query letters and more. Classes are held in the museum's Robert Frost Cottage or in the adjacent, gorgeous garden. Cost is $275 for two days of instruction (four hours per day on Saturday and Sunday). Classes limited to only 15 participants. Reception and orientation held the first night. Heritage House Museum, 410 Caroline Street. For more information, call 305-296-3573.
• February 24 - March 27, 2010 - THEATER - Shirley Valentine by Willy Russell - Directed By Joy Hawkins. Red Barn Theatre, 319 Duval Street, Rear, Key West. Box office: 305-296-9911
• February 25, 2010 - FUNDRAISER - Friends of the Key West Library Bi-annual Fund Raiser - A catered affair with entertainment, to be held at the Studios of Key West, from 6 p.m. to 7:30 p.m., cost $100 per person. Call for more information call 305-293-0713.
• February 27 - 28, 2010 - ART - 45th Annual Old Island Days Art Festival - Open-air art show and market featuring oil paintings, watercolors, sculpture, photography and other works. Whitehead Street & Caroline Street, Key West. For more information, call (305) 294-1241.
  

March 2010

• February 24 - March 27, 2010 - THEATER - Shirley Valentine by Willy Russell - Directed By Joy Hawkins. Red Barn Theatre, 319 Duval Street, Rear, Key West. Box office: 305-296-9911
• March, every day - ART - Sculpture Key West 2010- Each year artists from Key West and beyond install a thoughtful, inventive, and often whimsical collection of outdoor sculpture. Be sure to visit all three locations: Key West Garden Club at West Martello Tower (southern end of White Street), Key West Tropical Forest & Botanical Garden (5210 College Road, Stock Island), and Fort Zachary Taylor Historic State Park (at the end of Southard Street). For more information, call 305-295-3800.
• March 4 & 5, 2010 - MUSIC - Honey Island Swamp Band - Get your groove on while this southern roots band fuses blues, rock, jazz, funk and swamp into a unique, funky, bayou sound. Awarded "Best Emerging Artist of 2009" by Offbeat Magazine. 10pm. (also 5:30 pm soundcheck on Friday). Green Parrot Bar. 601 Whitehead Street. FREE.
• March 6, 2010 - LOCAL COLOR - 48th Annual Conch Shell Blowing Contest - Watch enthusiastic contestants, from children to seniors, pucker up and demonstrate their shell-blowing talents. No cost to enter or to compete, and no experience is necessary. Conch shells are available for purchase for those who do not have their own. Contestants are encouraged to register for the event at the Oldest House from 11:30 to 1:00 pm on or before the day of the event. For further information call 395-294-9501.
• March 11, 2010 - MUSIC - Steel Pulse - Reggae powerhouse Steel Pulse plays the sunset pier of the Ocean Key House hotel. $25 in advance/$35 at the door. Doors open at 8pm. Call 305-295-7047 for more information.
• March 11-14, 2010 - FAMILY FUN - St. Mary's Catholic Church Annual Spring Carnival - Rides, games, and food. 4-day wristbands for sale at half price of daily admission. Buy them at St. Mary's school office until Thursday March 11, 9pm-5pm. $40 for the entire weekend. Otherwise, buy tickets at the gate. Truman Avenue & Windor Lane. For more information, call 305-292-3013.
• March 12-13, 2010 - ARCHITECTURE - House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information
• March 13, 2010 - CUBA - Hot Havana Nights - A night celebrating and enjoying Cuban culture. Features a hot salsa band, silent auction of Cuba art, Cuban food, and mojito & cigar bar. VIP seating $125 includes seating dining. $50 for buffet & cash bar. 7pm - 11pm. 5210 College Road, Stock Island. Early reservations are suggested. Call 305-296-1504 for more information.
• March 18-20, 2010 - THEATER - Always… Patsy Cline by Ted Swindley - Directed By Joy Hawkins. Red Barn Theatre presenting at the San Carlos Institute, 516 Duval Street, Key West. Box office: 305-296-9911.

April 2010:

• continuing until April 16, 2010 - ART - Sculpture Key West 2010- Each year artists from Key West and beyond install a thoughtful, inventive, and often whimsical collection of outdoor sculpture. Be sure to visit all three locations: Key West Garden Club at West Martello Tower (southern end of White Street), Key West Tropical Forest & Botanical Garden (5210 College Road, Stock Island), and Fort Zachary Taylor Historic State Park (at the end of Southard Street). For more information, call 305-295-3800.
• April 7 - May 8, 2010 - THEATER - Short Attention Span Theatre - "A Myriad of Directors and A Cast of Thousands." Red Barn Theatre, 319 Duval Street, Rear, Key West. Box office: 305-296-9911.
• April 10 - 11, 2010 - AVIATION - 2010 Southernmost Air Spectacular - Featuring the Blue Angels in their famous F/A-18 Hornet jet fighters. U.S. Naval Air Station Key West is hosting this rare event - inviting the public onto the Boca Chica Naval Air Station at mile marker 9. Admission is FREE. No pets, coolers, bags, alcohol, bicycles, roller blades, roller skates, skateboards, and weapons are permitted. 15,000 people attended the 2004 airshow - so expect road delays. Gates open at 9 am - 5 pm. Blue Angels are scheduled to perform at 2:30 pm each day. Many other aircraft will be featured throughout the day on land and in the air.
• April 11, 2010 - WRITING - 16th Annual Robert Frost Poetry Festival - Abbreviated schedule this year (normally a 5 day festival). Plans to announce winners of the International Poetry Contest and the Monroe County Poetry in Schools Contest. 410 Caroline Street. For more information, call 305-296-3573.
• April 17, 2010 - THEATER - John Wells and Carmen Rodriguez sing James Taylor and Linda Ronstadt- Directed By Joy Hawkins. San Carlos Building, 516 Duval Street, Key West.
• April 19, 2010 - FOOD - 15th Annual Taste of Key West - 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 commerative 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.
• April 23, 2010 - MUSIC - Key West Symphony Master Concerts Series III - Tennessee Williams Theater, 5901 College Road, Stock Island. For more information and tickets, call 305-296-1520.
• April 28 - May 2, 2010 - MUSIC - 15th Annual Key West Songwriters Festival - The 14th-annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings.
• April 21, 2010 - MUSIC - Key West Symphony Master Concerts Series III - Tennessee Williams
  Theater, 5901 College Road, Stock Island - 8pm. For more information and tickets, call 305-296-1520.

May 2010

• April 7 - May 8, 2010 - THEATER - Short Attention Span Theatre - "A Myriad of Directors and A Cast of Thousands." Red Barn Theatre, 319 Duval Street, Rear, Key West. Box office: 305-296-9911.
• May 6, 2010 - FUNDRAISER - Florida Keys SPCA Spring Social - Held at a private hangar at Key West International Airport, this is a fundraiser to build a much-needed new animal shelter. Hosted by Christopher Rounds, owner of Antonia's Restaurant on Duval Street, with silent and live auctions and entertainment by Carmen Rodriguez. Tickets cost $50 and are available at Antonia's, the FKSPCA shelter, or at the door. Please leave your pets at home.
• May 14 - 15, 2010 - HISTORY - Harry S. Truman Symposium - While President of the United States, Harry S. Truman visited Key West for eleven working vacations - staying at what is known today as "The Little White House". Symposium highlights include an interview with President Truman's former White House assistant Ken Hechler about Truman's relationship with General Douglas MacArthur and a conference of prominent scholars from the United States, Asia, and Europe that will explore the Truman administration's halting progress toward the creation of a new geopolitical balance in East Asia following World War II. Cost is $125 for the entire conference including banquet. For more information and registration, call the Little White House at 305-294-9911.
• May 15, 2010 - SPORTS - Key West Paddleboard Classic - Features competitors circumnavigating the island of Key West on paddleboards and other self propelled divisions. Registration is $35 in advance or $40 the day of the race. Smathers Beach. For more information, call 305-797-1174.
• May 22, 2010 - MUSIC - One Love Festival - Featuring The Original Wailers, Techno Dread, The Resolvers, and Suénelo. Food/Beer/Drinks on Site. No coolers permitted. Blankets and chairs welcome. $20 per person. Gates Open at 6pm, Truman Annex Waterfront (end of Southard Street)

June 2010

• June 9-13, 2010 - GAY/LESBIAN - Pridefest Key West 2010: Diversity In Paradise - Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world's top gay and 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. Annual Pride Kick-Off is Wednesday, June 9th from 5:30 to 7:30 PM - sponsored and hosted by Island House 1129 Fleming Street (enter from White Street). Complimentary well drinks, domestic beer, house wine and hors d'oeuvres. An admission charge will benefit the Key West Business Guild and Key West PrideFest 2010. For more information, call (305) 292-3223.
• June 12, 2010 - SPORTS - The Original FKCC Swim Around Key West - Swimmers, accompanied by kayakers, circumnavigate the island of Key West, a distance of over 12 miles. For more information, call 305-809-3562.

July 2010

• July 4, 2010 - 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, 2010 - BAR STROLL - 2nd Annual 4th of July Bar Stroll - Honoring our military and Key West's penchant for fun, this event visits 9 local bars and restaurants for tastings and beverages. $25 admission fee includes commemorative t-shirt. $1000 in free entrys to active local military. Starts at 2pm at Dante's, 951 Caroline Street. Call 305-766-0239 for more information.
• July 20-25, 2010 - HEMINGWAY - 30th Annual Hemingway Days - Weeklong celebration of Ernest Hemingway, who lived in Key West during the 1930s. Events include running of the bulls, Hemingway look-a-alike contest, short-story contest directed by Hemingway's granddaughter, and billfish tournament.
• July 28-29, 2010 - 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 Salwater 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 2010

• August 6-8, 2010 - SEAFOOD - Key West Lobsterfest 2010 - 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 09, 2010 - ARTS - 4th Annual Midsummer’s Night Dream and Salon Spectacle - Celebrate a wonder-filled Midsummer’s Night Dream Party – a day and night of artistic expression, 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 Gardens to benefit Art Behind Bars and The Tropical Forest and Botanical Gardens. Adult admission: $10.00. Children under age 12 Free. 5210 College Road. For more information call 305-394-3804.

September 2010

• September 7-12, 2010 - GAY/LESBIAN - Womenfest Key West - Lesbians and their 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 8, 2010 - MUSIC - Indigo Girls' Emily Saliers Plays at the Armory - As part of the Womenfest Key West, this concert features the Grammy Award winning artist performing in the historic Armory building. Tickets cost $25. VIP reception + seating available for $75. 7pm showtime. 600 White Street. Call 305-296-0458 for more information.
• September 10-12, 2010 - FISHING - S.L.A.M. Celebrity Tournament - Some of the best Florida Keys flats fishing guides are paired with celebrities targeting Permit, Bonefish, and Tarpon. Benefits efforts to treat and cure cystic fibrosis. For more information, call 305-664-2002.
• September 16-19, 2010 - MOTORCYCLE - 38th 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. Riders who want to participate in this year's 37th Annual Phil Peterson’s Key West Poker Run can sign up at Peterson’s Harley-Davidson of Miami, N.W 194th Street, and U.S. 441 or at the new Peterson’s Harley-Davidson South, S.W. 198th St., and U.S. Highway 1 where the turnpike crosses over U.S.1 in Cutler Bay.You can purchase your poker hands starting September 1st, and until 12:00 noon on Saturday, September 19th. The Poker Run does not begin until Friday, September 18th at 8:00 a.m., and ends in Key West on Saturday at 5:00 p.m. We request a $10 donation per hand, and there is no limit to the number of hands you can play. 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 2010

• October 22-31 2010 - FANTASY FEST 2010 - Weeklong celebration - Key West's biggest party of the year - with many adult-only events. Events are detailed below.
• October 22, 2010 - FANTASY FEST 2010 EVENT - 30th Annual Goombay Fest - Stroll down Petronia Street from Duval Street and experience a world of Carribean flavors, street fair merchandise, and throngs of tourists and locals alike. A great time for all, look for live music on the street stage and at Blue Heaven. Starts at 12:00 noon. Ends at midnight. Free event.
• October 22, 2010 - FANTASY FEST 2010 EVENT - Royal Coronation Ball - The crowning of King and Queen of Fantasy Fest. Candidate with the largest fundraising benefiting AIDS Help becomes royalty. 6 pm, location to be announced. Call 305-296-6706 for more information.
• October 23, 2010 - FANTASY FEST 2010 EVENT - Friend's of Fort Taylor's Vampire Ball - Fort Zachary Taylor is decorated in the spookiest attire at "Key West's Funniest Halloween Haunting." This party features costume contest, music, dancing, food and beverages. Fort. Zachary Taylor State Park (at the end of Southard Street). 7-9 p.m. Cost: adults $13, children 10 & under $10. For more information, call 305-879-0091.
• October 23, 2010 - FANTASY FEST 2010 EVENT - 30th Annual Goombay Fest - Stroll down Petronia Street from Duval Street and experience a world of Carribean flavors, street fair merchandise, and throngs of tourists and locals alike. A great time for all, look for live music on the street stage and at Blue Heaven. Starts at 12:00 noon. Ends at midnight. Free event.
• October 25, 2010 - FANTASY FEST 2010 EVENT - Big 'Uns Lunar Lunacy Party - Bar party featuring music, drinks, and "full moon" contest with prizes for best "full moon". Cost is $25 and includes one drink. Location: Big 'Uns Sports Bar, 218 Duval Street - 9pm. Call 305-292-0486 for more information.
  
• October 25, 2010 - FANTASY FEST 2010 EVENT - 4th Annual Pinking of You! - Decorated Bra Auction - Features local artists decorating bras to be auctioned to benefit Womankind. 6pm; La Te Da 1125 Duval St. Call 305-296-6706 for more information.
• October, 26, 2010 - FANTASY FEST 2010 EVENT - Capt. 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 26, 2010 - FANTASY FEST 2010 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, 5 pm.
  
• October 26, 2010 - FANTASY FEST 2010 EVENT - 28th Annual Headress Ball - Dazzling headresses, created over many months, are worn and displayed in this awe inpiring event. HUGE works of art, each more inventive and imaginitive then the previous. Southernmost Hotel, 1319 Duval Street, Seating begins 7 pm, 8 pm. Buy tickets early as this event sells
  out. Call 305-296-1520 for tickets.
  
• October 26, 2010 - FANTASY FEST 2010 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. Call 305-293-0222 for more information.
• October 26, 2010 - FANTASY FEST 2010 EVENT - Big 'Uns Locker Room Romp - Bar party with sports costume theme. Prize for "best pom-poms". Cost is $25 and includes one drink. 218 Duval Street - 9pm. Call 305-292-0486 for more information.
• October 27, 2010 - FANTASY FEST 2010 EVENT - Big 'Uns "So You Think You're Sexy Enough?" Contest & Party - Nightly bar party with this night's theme dedicated to strip-tease dancing. Admission is $25 and includes your first drink. 218 Duval Street - 9pm. Call 292-0486 for more information.
• October 27, 2010 - FANTASY FEST 2010 EVENT - Guy Harvey's White Lace Black Light Event - Bar party at marine-artist's establishment. Guessing from the title, this event might feature everyone glowing purple. 511 Greene St.; 7p.m. Call 305-295-0019 for more information.
• October 27, 2010 - FANTASY FEST 2010 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. 4:30 pm, Casa Marina Resort, 1500 Reynolds St.
• October 27, 2010 - FANTASY FEST 2010 EVENT - Celebrity Look-a-Like Contest - Plenty of double takes as contestants compete for prizes. Crowne Plaza La Concha Hotel, 430 Duval Street. Contestant sign up 8 pm; FREE to watch; FREE to enter.
• October 27, 2010 - FANTASY FEST 2010 EVENT - Dungeon of Dark Secrets & Fetishes - Leather & fetish party. - 801 Bourbon Bar; Call (305)293-9800 for more information;9 pm at 801 Duval Street.
  
• October 27, 2010 - FANTASY FEST 2010 EVENT - Fogarty's Red Night - 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 28, 2010 - FANTASY FEST 2010 EVENT - Cowboy Bill's 4th Annual Git-R-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 28, 2010 - FANTASY FEST 2010 EVENT - Monster's 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 28, 2010 - FANTASY FEST 2010 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 28, 2010 - FANTASY FEST 2010 EVENT - Sloppy Joe's 27th Annual Toga Party - Sloppy Joe's 27th Annual Toga Party - Dress in a toga (extra points for incorporating this year's Fantasy Fest theme: “Habitat for Insanity.”) Contest at 9:30 pm. If you want to compete, free registration is at 8pm. 201 Duval St.
• October 28, 2010 - FANTASY FEST 2010 EVENT - Dante's 4th Annual Halos & Horns Pool Party and Wet T-Shirt Contest - Features prizes, live music, free body painting, and naughty-themed antics. 12pm - 6pm, 951 Caroline Street.
• October 28, 2010 - FANTASY FEST 2010 EVENT - Pajama and Lingerie Party - Featuring Playboy model Kristy Morgan. 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 29, 2010 - FANTASY FEST 2010 EVENT - Pimp and 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 29, 2010 - FANTASY FEST 2010 EVENT - Southernmost Sickos and Psychos Costume Contest - 3:00pm – 4:30pm Registration for Costume Contest at the Southernmost
  Hotel, 4:30PM contest begins. 6pm features Masquerade March 1/2 way party poolside. 1319 Duval Street. Free event.
• October 29, 2010 - FANTASY FEST 2010 EVENT - 9th Annual 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 29, 2010 - FANTASY FEST 2010 EVENT - Fairvilla Megastore Masquerade March - Wander through Key West's quaint Old Town historic distric with hundreds of other costumed
  
• participants. Beverage breaks along the way keep the merriment flowing. Begins at Francis Street & Key West Cemetary at 5pm. FREE.
• October 29, 2010 - FANTASY FEST 2010 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 29, 2010 - FANTASY FEST 2010 EVENT - Rum Barrel's 4th Annual Pirate Bash - Dress like a pirate and shake your booty. Prepare to aaaaargh all night. 9pm, Pirate Soul Bar & Restaurant, 528 Front Street. Call 305-292-7862 for more information.
• October 29, 2010 - FANTASY FEST 2010 EVENT - 801 Bourbon Bar Tea Dance - Street party with live DJ, cool drinks, dancers, drag queens and celebrities. 801 Duval Street - 1pm. Call
  
• 305-294-4737 for more information. FREE event.
• October 29, 2010 - FANTASY FEST 2010 EVENT - Fetish & Fantasy Party - Clothing optional Adults only/Men only party features costume contest & "special" dungeon. Island House - 1129 Fleming St.; 8:30 p.m. to 4:00 a.m.; call 305-294-6284 for more information.
• October 29, 2010 - FANTASY FEST 2010 EVENT - Habitiat for Insanity at Pearl's Rainbow for Women - Features music and dancing at this women-only resort. Contest for hot contestants. $20 includes one drink. 525 United Street - 8pm-11pm. Call 305-292-1450 for more information.
• October 30, 2010 - FANTASY FEST 2010 EVENT - Bourbon Street Pub Tea Dance and Balcony Brouhaha - Like parties of old, this event features DJ, dancing on Duval Street, and a cast of Key West's gay and gay-friendly characters. 11am - 5pm. 724 Duval Street. Bourbon Street Pub Complex. Call 305-293-9800. Free for non-VIP seats.
• October 30, 2010 - FANTASY FEST 2010 EVENT - Duval Street Promenade - Show off your costume on Duval Street. 12:00 pm - 10:30 pm. FREE event.
• October 30, 2010 - FANTASY FEST 2010 EVENT - Epidermal Arts and Torso Tapestries - Tattoo and body paint competition features unique and varied works of body art. Green Parrot Bar; 601 Whitehead St. 3 pm; Call 294-6133 for more information. FREE event.
• October 30, 2010 - FANTASY FEST 2010 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 cover Key West's most famous street. Parade route: 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 31, 2010 - FANTASY FEST 2010 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 31, 2010 - FANTASY FEST 2010 EVENT - The Fat Lady Sings Tea Dance - Last official event of Fantasy Fest, 4pm - 9pm. LaTeDa, 1125 Duval Street, call (305)296-6706 for more information. $5 per person.

November 2010

• November 4-7, 2010 - MUSIC - 19th Annual Meeting of the Minds 2010 - Parrothead convention nirvana benefiting charity. Many events are member only. Live shows including members of Jimmy Buffett's band. Who knows - maybe Mr. Buffett himself will show up (not likely). Check out the Margaritaville Street Fest 1pm-6pm on Duval Street (near Fleming Street) which is FREE and open to the public.
• November 6-13, 2010 - BIKE - Bubbafest Bike Fest Tours - Newly created and funded bicycle adventure with the focus on manageable rides (average 45 miles per day), fun activities, and oceanfront "resort" camping with most breakfasts and dinners included with registration. Event is limited to the first 125 riders and expected to quickly fill up. Early reservations are suggested. $595 rider fee. For more information, call Bubba at 321-759-3433.
• November 7-14, 2010 - SPORTS - 30th 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.

December 2010

• December 4-5, 2010 - SPORTS - Key West Triathlon - A first for Key West, athletes swim, bike, and run to the upper limits of endurance in this officially sanctioned triathlon. For more information, call 305-294-0693.
• December 10-11, 2010- HOLIDAY- Historic Lighted Inn Tours - Self guided tour of historic inns - decorated for the season and featuring art, gourmet food, and beverages. 5:30-8:00pm. $20 tickets may be purchased at Voltaire Books, corner of Eaton Street and Simonton Street.
• December 17-18, 2010- HOLIDAY- Historic Lighted Inn Tours - Self guided tour of historic inns - decorated for the season and featuring art, gourmet food, and beverages. 5:30-8:00pm. $20 tickets may be purchased at Voltaire Books, corner of Eaton Street and Simonton Street.
• December 28-29, 2010 - - ARCHITECTURE - 51st Annual House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information

2011 Key West Calendar of Events

January 2011

• January 17-21, 2011 - SAILING - Premier Racing Presents: Key West 2011 - 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. Call (781) 639-9545 for more information.
• January 21-22, 2011 - - ARCHITECTURE - 51st Annual House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information
• January 29-30, 2011 - ARTS - The 26th 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.

February 2011

• February 18-19, 2011 - ARCHITECTURE - 51st Annual House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information
• February 26-27, 2011 - ARTS - The 46th 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.

March 2011

• March 5, 2011 - LOCAL COLOR - 48th Annual Conch Shell Blowing Contest - Watch enthusiastic contestants, from children to seniors, pucker up and demonstrate their shell-blowing talents. No cost to enter or to compete, and no experience is necessary. Conch shells are available for purchase for those who do not have their own. Contestants are encouraged to register for the event at the Oldest House from 11:30 to 1:00 pm on or before the day of the event. For further information call 395-294-9501.
• March 18-19, 2011 - ARCHITECTURE - 51st Annual House and Garden Tour - Visit 5 Key West homes and tropical gardens.  Tickets are $25. Call 305-294-9501 for more information

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

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