Family FunBoat Tours

Enjoy your Mother's Day aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. This is a Key West Mother's Day Brunch Cruise you don't want to miss! Take in the vibrant colors of Key West as you sip champagne, dine on passed a delicious brunch, and glide through the crystal clear surrounding waters. This two-hour day sail features two complimentary alcoholic beverages. Brunch is provided, including bagels and pastries, meats and cheeses, smoked salmon, quiche, crudite, and other delicious treats! 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 sailing experience!

Looking to get out on the water? Consider this fun Florida Keys Day Sail! A Key West sightseeing cruise aboard the Schooner America 2.0 is the best way to experience our beautiful waters. This Key West day sail is the perfect family activity too! Sail past Fort Zachary Taylor, Mallory Square and then head out into the emerald green waters that Key West has to offer. Light narration provided by the captain and crew will orient you to all the sights visible from the waterfront, and you’ll learn about the unique ecology and history of the beautiful Florida Keys! On this Key West sailing adventure, there is even a chance that our day sail will turn into a dolphin watching cruise! So, bring your family and friends and join our attentive crew for this adventurous day sail that completes the Key West experience in comfort and style!

Back in the days of the yore, ships from afar carrying goods often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the pirates in Key West heard there was booty to be had, they'd jump in their boats and have a good ol’ pirate ship race out to the reef. The first one there could claim the ship's cargo! Arrggh!

Today, we playfully remember this history with a sailing race out to the Sand Key Lighthouse. It all starts with a cannon firing, and then all of the schooners of Key West are on their way! The boat that gets there first "wins" the Schooner Wharf Bar Wrecker’s Cup at an evening awards ceremony. Enjoy the excitement on this Key West sailing adventure aboard Schooner America 2.0 as we race for victory! This is a fun Key West schooner race and family-friendly activity 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 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!

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!

All hands on deck! Join us on this 2-hour Key West sailing adventure aboard one of the Florida Keys most stunning sailboats, the 105-foot Schooner America 2.0. Be a part of this annual festivity as we participate in a Civil War Sea Battle (on the Union side, of course!) Soak up the sun on this Key West afternoon sightseeing boat ride! If you’re looking for a fun Civil War reenactment, this Key West family activity is a must do! But, watch out for cannon fire!

On this Key West Easter cruise aboard the Schooner America 2.0, you’ll enjoy the vibrant colors of Key West waters as you sip on mimosas, dine on a delicious brunch, and glide effortlessly along under full sail. This Easter brunch cruise is one of Key West’s premiere holiday cruises and features two alcoholic beverages (for adults 21+), soft drinks, and water. Brunch includes bagels and pastries, charcuterie, smoked salmon, quiche, crudite, and other delicious treats! This is a family cruise in Key West not to be missed!

Join us for an unforgettable viewing party aboard the Schooner America 2.0 to experience the Blue Angels Air Show!

Looking to watch the Blue Angels Air Show? Classic Harbor Line Key West is offering a Blue Angels cruise aboard America 2.0! Your adventure includes three complimentary premium beverages and a delicious, gourmet lunch from a local bakery! As the Blue Angels take to the sky, watch their breathtaking aerial maneuvers from the best seat in the house, the open deck of our Key West yacht. Feel the excitement and energy of the show, enhanced by the comfort and elegance of our classic Key West schooner. This incredible event only occurs once every two years, so don't miss this exclusive opportunity to enjoy world-class entertainment and exceptional hospitality on the open water.

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.