Hoist the sails – if you’d like to lend a hand – aboard the grand dames of Key West’s sailing fleet, and enjoy the famous sunset.

Tall ship schooner with full sails up just before sunset in Key West
A sail aboard these vessels conjures Key West’s early days, when schooners were the work vehicle of their day, and the island was accessible only by boat.

Sailing the waters of Key West aboard a tall ship is an adventure most want to repeat.

Majestic and towering, these vessels remind admirers of Key West’s rich maritime history.

You can relax aboard one of the island’s historic schooners, each spacious and impressive.

With tall wooden masts securing their billowing sails in the breeze, the ships leisurely meander the calm waters as the sun sets.

The boats are very stable and offer drinks for the duration of the sail. The crews are happy to oblige guests who want to help hoist the sails.

Here are our favorites:

Schooner Appledore Star – AVAILABLE YEAR ROUND

Schooner Appledore Star under full sail
Schooner Appledore Star

68′ all-wooden schooner built in Maryland in 1982.  This impressive double-masted sailing vessel has a length-on-deck of 49 feet, draws 4-feet of water with the centerboard up, and has 14.5 feet of beam (that’s “width” for you landlubbers). The chair-height cabin top provides comfortable roomy seating.  On-board is a marine bathroom (that’s “head” for you landlubbers). She is an elegant vessel on the water with a capacity of 22 passengers.

What to expect:

Check-in 30 minutes prior to your trip start time at the Historic Seaport.  You’ll sail from downtown, leisurely entering the harbor and out to sea.  Many ships will be sailing nearby, and you will have plenty of scenery to enjoy, including an expansive view of Key West and the spectacular sunset. Includes hors d’oeuvres, premium beer, and wine, champagne, soft drinks.

Times:

6:30pm – 8:30pm daily during summer, 5pm – 7pm during winter. (Available Year Round)

Cost:

$79 per person

For reservations and information:

 Secure Reservations

 

Schooner America – AVAILABLE DURING WINTER MONTHS ONLY

The magnificent Schooner America, under full sail
Schooner America

The Schooner America is quite an impressive vessel. This majestic ship is a reproduction of the famous and fast sailboat that won the America’s Cup race in the mid-nineteenth century. Measuring 105′ overall, this ship is an engineering marvel, combining modern construction techniques with her classic lines.

What to expect:

Check-in 30 minutes prior to your trip start time.  You’ll depart from the Historic Seaport and sail among the rest of the fleet of sunset sailboats.  Enjoy the spacious and beautiful ship while enjoying beverages and snacks.  Includes premium drinks, beer, wine, champagne, soft drinks, shrimp cocktail, cheese and crackers, and veggie platters.

Times: 

4:30 pm – 6:30 daily. Available November to April.

Cost:

$96 per person

For reservations and information:

Secure Reservations

Schooner Appledore II – AVAILABLE DURING WINTER MONTHS ONLY

Schooner Appledore with a group watching the sun set over the ocean in Key West
Schooner Appledore II

Traditional, 86-foot, double-masted schooner.

Built in 1978, its maiden voyage circumnavigated the planet. This all-wooden vessel is extremely stable and strong.

You will not soon forget the beautiful bright-work (varnished wood), towering masts, and huge billowing sails.

This trip is only available during the winter season – from Thanksgiving to Memorial Day.

What to expect:

Check-in 30 minutes prior to your trip start time.  You’ll sail from the Historic Seaport in downtown Key West, through the harbor and up to a couple miles offshore.  Includes premium beers, wines, soft drinks, fruit & cheese platters.

Times:

5:00 pm – 7:00 pm, available Thanksgiving to Memorial Day – UNAVAILABLE DURING THE SUMMER MONTHS

Cost:

$69.95 per adult
$34.95 for children 12 & under.

For reservations and information:

Secure Reservations

 

Schooner Western Union – CURRENTLY UNAVAILABLE

The historic schooner Western Union, with all sails up
Schooner Western Union

Officially named the flagship of the State of Florida, the Schooner Western Union is a true floating piece of maritime history. Built in 1939 in the Caymans and finished in Key West, the all-wood, gaff-rigged vessel was constructed to maintain communications cables between the US, Cuba, and the Caribbean. This vessel has 5200 sq. feet of sail, has an overall length of 130′, a wide 23.5′  beam, and capacity of 76 passengers.

What to expect:

Check-in 30 minutes prior to your trip start time at the Historic Seaport.  You’ll sail from downtown, leisurely entering the harbor and out to sea.  Many ships will be sailing nearby, and you will have plenty of scenery to enjoy, including an expansive view of Key West and the spectacular sunset. Includes beer, wine, champagne, soft drinks, conch chowder, cannon firing, and dove release.

Times:

7pm – 9pm daily during summer, 5pm – 7pm during winter. (Available Year Round)

Cost:

$99 per adult, $59 per child 12 and under.

UPDATE: The Western Union is not in service, since July 31, 2013.  The vessel is undergoing major maintenance. We look forward to the day she is back where she belongs – in Key West.