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Key West, FL

Romantic Sails

Romance in Key West

Take to the water and fall in love all over again aboard a Key West Romantic Sunset Sail. We know there are a lot of romantic things to do in Key West, but the most unique and romantic thing to do in Key West is step aboard our classic yacht for an unforgettable memory. Choose from a variety of Key West Cruises for your special evening:  Pick a Key West romantic sunset sail, or a romantic boat ride through the night on a Key West Full Moon sail.  

Take a deep breath, relax and feel the wind in your hair. Sip on Champagne and have a quiet, intimate conversation with your loved one as you drift by Mallory Square or cruise over to Fort Zachary Tayler. Sit aboard this classic boat and have moments of laughter and take in the breath taking views. Whether it is a Key West Sunset Sail, Full Moon Sail or one of our Special Holiday Events you and your loved one will share an experience that will last a life time and you are sure to make this a regular date idea.


Key West Sunset Sail

Sunset Sail aboard Schooner America 2.0

Enjoy your classic Key West sunset sail aboard the most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West’s famous sunset as you sip champagne, dine on passed hors d’oeurves, and glide through the crystal clear surrounding waters. This two-hour Key West sunset sail features complimentary champagne, wine, beer, soft drinks, and water. Passed hors d’oeurves are provided, including shrimp cocktail, a cheese plate, and delicious veggies! Schooner America 2.0 is a state of the art vessel built in 2011. She features teak decks, mahogany-trimmings, and 3600 square feet of canvas! Sit back and relax while she plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience!

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $85

Key West Full Moon Sail

Full Moon Sail Aboard Schooner America 2.0

A Key West Full Moon Sail is sure to take your breath away.  Take to the Key West waters by Full Moon Light!! This romantic, moonlight sailing adventure is yours aboard Key West’s most stunning sailboat, the 105-foot wooden schooner, America 2.0. America 2.0 features teak decks, mahogany-trimmings, and just under 3600 square feet of canvas! Sit back and relax on this Key West Full Moon Sail while she slices through the evening, basking in the golden moonlight that dances in the night waters. This special sail features complimentary beer, wine, champagne, soda, and water. Guests are encouraged to make the most of the event by bringing aboard their own picnic!

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $45

Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the fastest, most elegant schooner, the brand new eco-friendly, America 2.0 as we parade through the Bight and Harbor of Key West!  She’ll be fully decorated in Holiday decor with up to 30 other Key West vessels in the annual Key West Lighted Boat Parade. Cruise aboard America 2.0 while taking in this magical display of holiday spirit. All of these vessels will have the opportunity to show off their creative and imaginative holiday decorations as they glide by the viewers and judges at the Schooner Wharf Bar.

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $85 | Child $45

Key West New Year's Eve Event

New Year’s Eve Bash aboard Schooner America 2.0

Join us aboard America 2.0 for a wonderful New Year’s Eve Bash! This Key West New Year’s Eve Event aboard the Schooner America 2.0 is one that must not be missed.  Enjoy this timeless celebration on the most exclusive boat in the Historic Bight, and experience VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench” from the rig of Schooner America 2.0! This special ’21 and older’ event features complimentary beer, wine, champagne, well drinks, soda, water, and delicious hors d’ oeuvres! The Key West New Year’s Eve Event will separate you from the crowds and give you the best seat in the house for a front row viewing of the Lowering of the Pirate Wench.  

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $165

Key West Valentine's Day Sunset Sail

Champagne & Aphrodisiacs Valentine’s Day Sail

This Valentine’s Day, take to the water and fall in love all over again. Join Schooner America 2.0 on a Key West Valentine’s Day Sunset Sail for an unforgettable sunset that is sure to tickle your taste buds and create a memory to last a lifetime. Celebrate this Valentine’s Day with your special someone on our Champagne and Aphrodisiacs Pairing Sunset Sail in Key West. As you sail along the beautiful turquoise green waters on the Schooner America 2.0, you and your loved one will be able to take in all the romance that this Key West Valentine’s Day Sunset Sail has to offer while being treated to a delicious pairing menu that is sure to entice consisting of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world!

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Price Varies $85 - $125