Key West DecemberCruises and Events

There is simply nothing better than sailing at sunset in Key West. So, why experience it on anything other than the best Key West sunset cruise aboard the Schooner America 2.0? Glide through emerald green waters with the wind in your hair and the sea breeze on your face. Enjoy a Key West romantic sunset sail in an elegant and relaxing atmosphere, complete with comfortable bench seating and refreshments. Witness the breathtaking Key West sunset, renowned for its vibrant colors, and keep an eye out for playful dolphins and the elusive Key West “Green Flash!” This picturesque and sunset boat tour is the perfect way to end your day in Key West and create unforgettable memories.

Let us whisk you and yours away on a glorious morning cruise across the beautiful waters of Key West on your own private yacht! This 1.5+ hour private sailing experience aboard the Schooner America 2.0 grants you all the luxuries of yachting on your own private sailing yacht without the huge price tag, or the maintenance! This is the perfect way to start your day of sightseeing in Key West! Just sit back and relax, surrounded by your loved ones, friends, or co-workers, and let us take care of the rest.

Start your Key West New Year’s eve celebration off with a sunset sail. Experience an unforgettable Key West New Year’s Eve sunset cruise aboard the Schooner America 2.0! Get into the holiday spirit with your friends or family as you sail through the beautiful waters of Key West with the wind in your hair and the sea breeze on your face. Enjoy an elegant and relaxing atmosphere while our crew serves you delicious refreshments, including beer, wine, champagne, and hors d’oeuvres on this Key West New Year’s Eve sunset cruise. Witness the breathtaking Key West sunset, renowned for its vibrant colors and the elusive “Green Flash,” and keep an eye out for playful dolphins. Finally, finish your sunset sail with a special champagne toast and a souvenir champagne flute to take home and remember your perfect vacation. This picturesque New Year’s Eve celebration is the perfect way to end your year in Key West!

Please join us for this special Key West warm and cozy holiday cruise tailored for friends, family, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 decorated in CHristmas lights and other fun 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 other treats for all our guests are included! Sit back and enjoy your Christmas in Key West on this family holiday cruise! America 2.0 features the best in comfort- teak decks, mahogany-trimmings, and a soaring rig! Sit back and take a ride on this decorated schooner while you enjoy the festivities of the evening with your family and friends. Join our courteous and professional crew for this evening celebration cruise that will highlight your Key West Christmas experience!

Prepare to be dazzled as you join fellow guests for the ultimate Key West New Year's Eve party. Enjoy VIP dockside access to the famous Schooner Wharf Bar "Lowering of the Pirate Wench" from the rig of Schooner America 2.0! From the moment you step onto the boat for this fun Key West dockside event, the Schooner America 2.0 provides the perfect backdrop for revelry, with spacious decks offering panoramic views of the harbor as your party into the night.This special '21 and older' New Year’s Eve event features complimentary delicious hors d' oeuvres and a full bar. Gather with friends and join our courteous and professional crew for this late night Key West New Year’s Eve boat party that will be the highlight of your Key West experience! This is a special New Year’s Eve celebration to ring in the New Year as the pirate wench is lowered as we countdown to midnight!

Experience an enchanting Christmas Eve sunset sail aboard the Schooner America 2.0, a state-of-the-art 105-foot vessel. Glide through the emerald green waters of Key West with the wind in your hair and the sea breeze on your face. Enjoy an elegant and relaxing atmosphere, complete with comfortable bench seating and refreshments, including beer, wine, champagne, and holiday themed hors d’oeuvres. Witness the breathtaking Key West sunset, renowned for its vibrant colors and the elusive “Green Flash,” and keep an eye out for playful dolphins. This picturesque sail is the perfect way to end your day in Key West, creating unforgettable holiday memories.

Built in 2011, the Schooner America 2.0 is equipped with teak decks, bench seating, and a vast 3600 square feet of canvas. Relax as she sails smoothly through the turquoise waters of Key West, offering a quintessential holiday sunset sail experience.

Experience a magical Christmas Day sunset sail aboard the Schooner America 2.0, a cutting-edge 105-foot vessel. Drift through the emerald waters of Key West, feeling the wind in your hair and the sea breeze on your face. Relax in an elegant atmosphere with comfortable bench seating and enjoy refreshments, including beer, wine, champagne, and holiday-themed hors d'oeuvres. Marvel at the breathtaking Key West sunset, famous for its vibrant colors and the elusive "Green Flash," and keep an eye out for playful dolphins. This picturesque sail is the perfect way to conclude your day in Key West, creating unforgettable holiday memories. Schooner America 2.0, constructed in 2011, boasts teak decks, cozy bench seating, and an impressive 3600 square feet of canvas. Enjoy a serene voyage through the turquoise green waters of Key West, gliding towards the horizon for an ideal Key West sunset sail experience.

Enjoy the vibrant colors of Key West as you sip champagne, dine on a delicious brunch, and glide through crystal clear surrounding waters on one of Key West’s premiere holiday cruises. This Christmas brunch Key West-style features complimentary mimosas, bloody marys, champagne, wine, beer, soft drinks, and water. Brunch includes spiral ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, quiche, and other delicious treats! This is one of the few Christmas Day events in Key West not to be missed! Built in 2011, Schooner America 2.0 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 holiday brunch experience!

Join us for the Key West Annual Lighted Boat Parade aboard Schooner America 2.0! Adorned in festive lights, the America 2.0 is a dazzling spectacle on the water. Watch from our beautiful teak decks and comfortable bench seating as boats of all sizes glide through Key West harbor, illuminated in a vibrant display of colors and decorations. Onboard, enjoy the holiday atmosphere with music, refreshments, and the company of fellow revelers. As the Christmas parade progresses, marvel from a prime viewing spot onboard at the creativity and ingenuity of each boat's decorations. This enchanting event aboard Schooner America 2.0 offers a unique perspective on the holiday season and creates lasting memories for all!

Please Note: We will not be raising sails during the parade due to maneuverability.