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Key West, FL

Sailing

Sailing with Classic Harbor Line A must do while on vacation is some Key West Sailing!  Join us with our professional crew and take to the waters of Key West. Let our crew dazzle you with their skills of sailing our yacht and taking care of you with the up most hospitality. Sailing is fun, but sailing and sightseeing is the most magical way to experience this Island of wonder.

Enjoy a Key West Sunset Sail or sail past Mallory Square, and cruise by Fort Zachary Taylor. Allow the dolphins to take your breath away as they surf the bow of our boat on our Key West Day Sail.  You will truly enjoy the excitement and art of Key West sailing.

While sailing aboard the 105 foot Schooner America 2.0 you will experience the most premium sailing. This stunning classic boat was designed for comfort and speed.  So snap some photos and sip on Champagne as you cut through the emerald green waters of Key West. 


Key West Sunset Sail

Key West Sunset Sail on Schooner America 2.0

Enjoy the best Key West sunset sail on Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip champagne, and dine on passed hors d’oeurves. On this Key West Sunset Cruise you will magically glide through the crystal clear surrounding waters.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water. Passed hors d’oeurves are provided, including shrimp cocktail, a cheese plate, and delicious veggies! 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!

  Duration: 2 hrs   Boat: America 2.0   Cost: Adult up to $96

Key West Mimosa Sail

Key West Mimosa Sail on Schooner America 2.0

Good Morning Mimosa Lovers! Step aboard for a Key West Mimosa Sail on our stunning Schooner America 2.0! Start your day off right and take the helm and experience the power of this sailing machine.  Or sit back and relax while with a mimosa in hand as you sail smoothly through the crystal clear waters of Key West. Either way and above all, it doesn’t get much better for an afternoon day sail in Key West. This 1.5 hour sail features a complimentary mimosa bar, beer, wine, champagne and soft drinks! Bloody Marys are for purchase (credit card only)! A small hors d’oeurves plate is served, but guests are encouraged to bring aboard their own picnic lunch!

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult up to $64

Key West Day Sailing

Classic Day Sail aboard Schooner America 2.0

It is true! When in Key West you must soak in the sun while you do some classic Key West day sailing. We think the best way to spend an afternoon is to take to the water on the Schooner America 2.0 for a Key West Day Sail! Named after the first boat to win the America’s Cup in 1851. Our stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating. There is over 3,600 square feet of sail that will propel you smoothly through the crystal green waters of Key West. Our 1.5-hour Classic Key West Day Sail features complimentary beer, wine, champagne and soft drinks. We have Bloody Marys that are for purchase (credit card only)! Also, a small hors d’oeurves plate is provided, but guests are encouraged to bring aboard their own picnic lunch.

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult up to $64

Key West Wreckers Race

Wreckers Race aboard Schooner America 2.0

All hands on deck!  It is an absolute must for you to join us for the Key West Wreckers Race! Sail aboard the Schooner America 2.0 for this 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 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.  All of the schooners take off and 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.  The winners are announced and treasures collected.

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $96

Key West Full Moon Sail

Full Moon Sail Aboard Schooner America 2.0

Let us take your breath away with a Key West Full Moon Sail.  A truly magical way to experience Key West is to take to the waters by full moon light! This is the most romantic, moonlight sailing adventure that is yours to be had aboard Key West’s most stunning sailboat.  Our 105-foot wooden schooner, America 2.0 is the most elegant schooner in town.  Sit back and relax with us on this Key West Full Moon Sail while cruising through the evening. Basking in the golden moonlight that dances on the night waters you are sure to have a memorable event. You will enjoy complimentary beer, wine, champagne, soda, and water. We encouraged you to make the most of the event by bringing aboard your own picnic!

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $56

Key West Wreckers Race

Key West Classic Regatta

The Key West Classic Regatta is designed after the Great Chesapeake Bay Schooner race and is a great way to see some of the most beautiful Key West schooners in their element. It is time to jump aboard and take an adventure on Key West’s most stunning sailboat, the 105-foot Schooner America 2.0 and be a part of this annual festivity! So, all hands on deck! Join us as we push off the dock at 10:30 AM for race start! America 2.0 features beautiful teak decks, mahogany-trimmings, and with 3,600 square feet of canvas, she flys! Sit back and relax while she plies effortlessly through the crystal Green Key West sailing waters towards the finish line!

  Duration: 4.5 hrs   Boat: Schooner America 2.0   Cost: $85

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. 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $136

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.   

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

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!

  Duration: 4 hrs   Boat: America 2.0   Cost: Adult $116

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 us aboard Schooner America 2.0 on a Key West Valentine’s Day Sunset Sail.  This is an unforgettable sunset sail that will 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.

Our crew will cater to you as you sail through the beautiful turquoise green waters aboard 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. We will  treat you to a delicious pairing menu that is sure to entice.  The menu consists of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world! So look no further and join us for a romantic evening on the water. 

  Duration: 2 hrs   Boat: America 2.0   Cost: $186