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Key West, FL

Key West Schooner Wharf

Key West Schooner Wharf

Take to the water and fall in love all over again with Key West. Classic Harbor Line provides unprecedented views of modern-day Key West aboard old-world-style yachts. As designer, builder, and operator of classically inspired boats, our guests enjoy day and sunset Sails of the emerald green waters of Key West aboard finely crafted Schooner America 2.0 featuring teak decks, varnished mahogany rails and gleaming brass fixtures.

Experience the turn of the century of yachting while sailing today’s Key West Waters, with breathtaking views of the magical Key West Green Flash. Whether it’s non-narrated, lightly narrated or fully narrated, each excursion is its own unfolding story.

Join us for a Day Sail, and sail alongside of the dolphins. Set sail at sunset and enjoy the hospitality of our Captain and Crew. Lighted Boat Parades and Sightseeing Sails will keep you engaged and the Full Moon Sails will be your next date idea. Whatever you choose you are sure to enjoy your time out of the water with us as our crew treats you with the most professional hospitality.

Day Cruises, Sunset Sails and the educational Brooklyn Waterfront Tour will keep you coming back for more whether you are a local or tourist. If this location does not have what you are looking for make sure to check out the Chelsea Piers location for a variety of other tours.


Key West Day Sailing

Classic Day Sail aboard Schooner America 2.0

Soak in the sun while you do some Key West Day Sailing!  Take to the water on the Schooner America 2.0, named for the first boat to win the America’s Cup in 1851 for some Key West day sailing. This stunning 105-foot boat features teak decks, mahogany trimmings and ample seating. Her 3,600 square feet of sail will propel you smoothly through the crystal green waters of Key West Florida. This 1.5 hour Key West day sail features complimentary beer, wine, champagne and soft drinks! Refreshing fresh fruit is provided, but guests are encouraged to make the most of the event by bringing aboard their own picnic lunch!

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $55 | Child $35

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 Wreckers Race

Wreckers Race aboard Schooner America 2.0

All hands on deck join us for the Key West Wreckers Race! Sail aboard the Schooner America 2.0 for the monthly Schooner Wharf Bar Wrecker’s Race! Back in the days of the yore, pirate ships from afar often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the scallywags in Key West heard there was booty to be had, they’d get in their boats and race each other out to the reef. The first one there could claim the ship’s cargo! Arrggh! Today, we celebrate it with the firing of the canon at 1:00pm to start the Key West Wreckers Race, and all of the schooners of are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, “wins”! Enjoy the excitement aboard Schooner America 2.0 as we race for victory! An awards ceremony takes place at 9 PM at Schooner Wharf Bar where the winners are announced and treasures collected.

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $75 | Child $35

Quantum Key West Race Week Spectator Sail on Schooner America 2.0

Quantum Key West Race Week Spectator Sail aboard Schooner America 2.0

Join us on America 2.0, the Official Spectator Vessel for the 2017 Quantum Key West Race Week! This exciting event happens every year in these emerald green waters and you are going to have the best seat in the house.  This is a week of sailing excitement that you do not want to miss out on. Schooner America 2.0 is a 105-foot schooner that has over 3600 square feet of sail, and a cutting edge free standing carbon fiber rig!  With comfortable wrap around seating you are sure enjoy a afternoon in the sun for the Quantum Key West Race Week Spectator Sail on Schooner America 2.0!

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $75 | Child $45

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