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Romantic Sails

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Romance in Key West

Well, if you are looking for something romantic we have the perfect idea! 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 while sipping on Champagne. Sit aboard this classic boat to enjoy 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 which you are sure to make this a regular date idea.


A large schooner sailing in Key West with the sun peaking through the sails for a Key West Sunset Sail

Key West Sunset Sail on Schooner America 2.0

Enjoy the best sunset sail in Key West on the Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip complimentary champagne.  On this Key West Sunset Cruise, you will magically glide through the crystal clear surrounding waters whilst being taken care of by our professional and friendly crew.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water and passed hors d’oeurves- veggie crudite, cheese and crackers, and shrimp cocktail. There is a cocktail bar on board for purchase. Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience! (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: America 2.0   Cost: Adult $108 | Child $54

Schooner America 2.0 sailing in the night for a Full Moon Sail!

Full Moon Sail Aboard Schooner America 2.0

Sail through the Key West waters by full moonlight on this romantic Full Moon sailing adventure aboard one of Key West’s most stunning modern sailboats, the 105 ft Schooner America 2.0. This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing, complimentary soft drink, and water. Drinks and snacks available for purchase. Pro Tip: Call us directly at 305-293-7245 to avoid the 6% online processing fee.

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $68 | Child $36

Schooner America 2.0 night sailing for a stargazing evening

Starry Night: Guided Stargazing Sail Aboard Schooner America 2.0

Join us aboard the Schooner America 2.0 after the sun goes down, setting the stage for an enchanting stargazing journey unlike any other. As the boat gently glides across the tranquil waters, your guide, a seasoned astronomer, narrates the celestial spectacle unfolding above. Pointing out constellations and tracing the mythology behind their names, they weave together tales of ancient cultures and their interpretations of the stars.

Wrapped in the darkness of the night sky, you marvel at the intricate details of distant planets, shimmering nebulae, and elusive galaxies. Each sighting is accompanied by insightful commentary from your guide, illuminating the mysteries of the universe. It’s an experience that transcends time, leaving you with memories that will twinkle brightly in your heart for years to come.

  Duration: 1.5 hras   Boat: America 2.0   Cost: General Admission $76

Schooner America 2.0 decorated for the Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for the Schooner Wharf Bar Annual Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the most elegant schooner decked out in holiday decor.  The America 2.0 will parade through the Bight and Harbor of Key West. We will be showing off our crew’s creative design of twinkling lights that will dazzle all! (Call us directly to save 6% online processing fee) 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $104

Schooner decorated in Holiday lights at a dock in key west.

Cocoa and Carols: Christmas Lights and Music Sail aboard Schooner America 2.0

Please join us for this special Key West warm and cozy holiday cruise tailored for friends, family, and all your loved ones during the Key West Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 in full holiday decor for a 1.5-hour cruise in Key West harbor while we listen to some of our favorite Christmas hits! Delicious Hot Cocoa, Cookies, and treats for all our guests are included! Sit back and enjoy this unique holiday sail in Key West on this family-friendly 1.5-hour cruise.
  Duration: 1.5 hrs   Boat: Schooner America 2.0   Cost: $56 Adults (Kids sail free)

The Schooner America 2.0 decorated for the New Year's Eve Lowering of the Pirate Wench

New Year’s Eve Dockside Bash aboard Schooner America 2.0

Do you want the best seat in the house for New Year’s Eve in Key West? Join us aboard America 2.0 for an epic Dockside New Year’s Eve Bash! Your ticket grants you VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench” as we lower her from the rig of our very own Schooner America 2.0! Enjoy this timeless celebration on the most exclusive boat in the Historic Bight. Our special ’21 and older’ event features complimentary beer, wine, champagne, well drinks, soda, water, and delicious hors d’ oeuvres all night! (Call us directly to save 6% online processing fee) 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $246

a couple being served Champagne on a Key West Valentine's Day Sunset Sail

Champagne Sunset Valentine’s Day Sail

Join us for our Key West Valentine’s Day Sunset Sail aboard the Schooner America 2.0!  This is a day to celebrate your loved one.  So spend Valentine’s Day in Key West aboard our elegant Schooner. It truly is the perfect way to show your love and appreciation. Sail through Key West with a glass flute of French champagne in hand and cruise aboard our classic boat for an evening of elegance.  Watch the sun dip beyond the horizon.  Snuggle up with your loved one to celebrate your love for each other.  Reflect on your relationship aboard this Valentine’s Day cruise.Our professional crew will cater to your every need. We will wine and dine you and make you feel like royalty. Key West sailing is a magical way to capture a moment in time.  So what better cruise to do this on then the Key West Valentine’s Day Sunset Sail.  This magical Key West sunset sail will take your breath away and your loved one will be swept off their feet all over again. (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: America 2.0   Cost: $136

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