A big “thank you” to Key West Food Tours for giving us a shout out at being in the top 10 Fabulous Key West February Events!  Ranked at number 5 we offer a romantic sunset sail on Valentine’s Day as well as running a classic key west sunset sail daily.  

Take a look to see what they suggest for the month of February!  Click here to read more.  

Sunset Sail Key West 

What best way to experience Key West than on a Key West Sunset Sail aboard a classic schooner!? Cruise with us into the horizon.  Sip on Champagne as we take you to a place you have never been before.  Our expertly trained Captain and Crew will give you a new kind of experience that is sure to last a lifetime.  We will take you on a magical sailing ride with the wind in your hair a your soul filled with joy.  

We also know that experiences become legendary stories for future generations to come.  Let us host you on an adventure that will leave you breathless and become the next story told to friends and family. 

Why would you pick us over the many Sunset Cruises in Key West?  Because our yacht is a contemporary design for a classic experience.  You will have old world charm with the speed and grace of the new.  So get your tickets now for your Key West Sunset Cruise and let us dazzle you as you kick back and relax. 

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

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Sail with us aboard the Schooner America 2.0 for this epic event!

Spend your Memorial Day Weekend with us at Sail Philadelphia for four days of waterfront festivities, ship tours, and sailing excursions on the Delaware River. Tall ships from U.S. and international ports will dock at Independence Seaport Museum and Penn’s Landing from May 24– 28. Details and information will be available at sailphiladelphia.org in the coming weeks, but you can begin planning your Memorial Day Weekend in Philadelphia, now by booking Ship Tour tickets here: and 90-minute Day Sails and 120-minute Twilight Sails here.

Schooner America 2.0 is our stunning, black-hulled, 105 foot sailing yacht and a tribute to the first Schooner America – winner of the first America’s Cup in 1851.  Sit on the open decks that feature comfortable seating and bar service for up to 76 and take in the view of these magical ships.

The Schooner America 2.0 will glide effortlessly through the waters and get upfront and personal views of the stunning yachts that will visit the Delaware River this coming May.  

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Schooner America 2.0 Aerial View from Classic Harbor Line on Vimeo.

Soak up the unique history as you walk through the old Key West Historic Seaport also known as the Key West Bight.  Home of many fabulous restaurants, bars and the famous Schooner America 2.0.  Breathe in the refreshing salty air. Listen to the sounds of the lines clanking on the masts of the tall ships docked in the marina.  Stop in at the legendary Schooner Wharf bar for a drink. Listen to some live music by the local talented Key West musicians before embarking on your sunset sail aboard Schooner America 2.0.  Get your tickets from our friendly sales representative located at our ticket booth just outside of the bar.  Step aboard and experience the best Key West sunset sail that the Keys has to offer aboard Schooner America 2.0. 

Reaching at 105 feet, this Schooner is a tribute to the original “Low black schooner: Yacht America” that won the very first Americas Cup Race in 1851.  The open teak deck features comfortable seating and bar service for up to 76.  Let our most professional crew cater to your needs as you watch the sun dip beyond the horizon.  Kick back and relax as the boat cuts through the emerald green waters and sip on a beverage of your choice to catch a glimpse of the green flash.  

Key West is known for its famous sunset, so why not do that aboard this tribute to the famous “Low black schooner”!  Whether you join us for a day sail, special event or go sailing for sunset you are sure to grab some amazing photos! It will definitely be a memory that will last a lifetime. 

Click here for your Key West Sunset Tickets.

Join us for the best seats in the house on this annual tradition of the “Lowering of the Pirate Wench”!  Each year we hoist the famous Schooner Wharf Bar Pirate Wench to the top of our 100 foot mast aboard the Schooner America 2.0.  Count down lights are hung from the top of the mast all the way down to the schooner deck. She is hoisted up for all to see and then dramatically drops down the mast with the count down lights to bring in the New Year!  Sit aboard with us and have the best seats in the house to celebrate New Year’s Eve in Key West.  Crowd free and comfortable sit with us and let our professional crew serve you your drinks and hors d oeuvres.