Key West, FL

Day Sailing


Because you love sailing we know you need to step aboard the Schooner America 2.0 and cruise with us for a Key West Day Sail!  Certainly, you cannot go wrong with sipping on some Champagne or a favorite beverage of choice as you kick back to relax with us.  Soak in that sun for the afternoon as you sail with us aboard this stunning yacht.  Depending on the weather we will head out to Fleming Key, Sunset Key, Sand Key Light House or Fort Zachary Taylor.  Catch a glimpse of the magical Key West dolphins as they surf the bow of our boat. Yes, they surf the bow of our boat and for that reason, you will be sure to capture a photo for your social media!  

We all know that sailing is a “must do” when in Key West, so step aboard and let us dazzle you with not only the most premium sailing experience but the most professional crew Key West has to offer. Our crew will cater to your every need and tell you the tales of old Key West as you cruise through the emerald green waters.

 If you are not interested in a Day Sail then make sure to  join us on our Champagne Sunset Sail!

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 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 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 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