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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.


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 $104 | Child $36

Key West 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, light snacks, soft drinks and water. Beer, wine, champagne, and cocktails are available on board for purchase, or you may purchase them in advance during the online booking process. Pro Tip: Call us directly to avoid the 6% online processing fee.

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $64 | Child $36

Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for the 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 crews creative and imaginative design of twinkling lights that will dazzle all.  Up to 30 other Key West yachts will join us in the annual Key West Lighted Boat Parade. Cruise aboard America 2.0 while taking in this magical display of holiday spirit. All of the participating yachts will have the opportunity to show off their holiday decorations as they glide by the viewers and judges at the Schooner Wharf Bar. (Call us directly to save 6% online processing fee)

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

Key West New Year's Eve Event

New Year’s Eve 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 New Year’s Eve Bash! Our Key West New Year’s Eve Event aboard the Schooner America 2.0 is one that must not be missed.  You will experience VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench”. We are the very venue that hosts the Lowering of the Pirate Wench from the rig of our Schooner America 2.0! So 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! Our Key West New Year’s Eve Bash will separate you from the crowds and give you the best seat in the house for a front row viewing of this epic event. (Call us directly to save 6% online processing fee)

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

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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