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Key West, FL

Day Sailing

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day-sail

Because you love sailing, we know you need to step aboard the Schooner America 2.0 and cruise with us for a Key West Classic Day Sail!  Soak in the afternoon sun as you sail with us aboard this stunning yacht. With the wind in our sails, we’ll head out into the harbor towards Fleming Key, Sunset Key, Sand Key Light House or Fort Zachary Taylor.  Catch a glimpse of Key West dolphins as they surf the bow of our boat. If we are lucky, we may even spot a turtle (that’s good luck, you know!)  

We all know that sailing is a “must do” when in Key West, so step aboard and let us impress 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 Classic 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. We boast a full bar on board which is available for credit card purchase. Soda and water are complimentary. Guests are encouraged to bring aboard their own picnic lunch! (Call us directly to save 6% online processing fee)

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $55

Key West Mimosa Sail

Private Morning Sail on Schooner America 2.0

Step aboard for a Key West Morning Charter on our stunning Schooner America 2.0! This 1.5 hour sail is available to book privately with your close friends and family. Start your day off right and take the helm and experience the power of this sailing machine.  Or sit back and relax as you sail smoothly through the crystal clear waters of Key West. Either way and above all, it doesn’t get much better for a morning sail in Key West. (Call us directly to save 6% online processing fee)

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Starting at $750

Key West Wreckers Race

Wreckers Race aboard Schooner America 2.0

All hands on deck!  If you enjoy a good sailboat race, it is an absolute must for you to sail on board the Schooner America 2.0 for the Key West Schooner Wharf Bar Wrecker’s Cup Race! 

A little history…back in the days of old Key West, ships from afar often ran aground on Sand Key Reef. When all the scallywags in Key West heard there was booty to be had, they jumped in their boats and raced to the reef. The first one there could claim the ship’s cargo! Arrggh!

Today, we celebrate this Key West tradition annually with a set of monthly races from January to April. It all starts with the firing of the cannon at 1:00 PM.  Enjoy the excitement aboard Schooner America 2.0 as we race to defend our title of fastest schooner in Key West!

Beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase. (Call us directly to save 6% online processing fee)

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

Key West Brunch Sail

Christmas Day Brunch Sail aboard Schooner America 2.0

Enjoy your Christmas Day morning aboard Key West’s most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0.  Take in the vibrant colors of Key West as you sip champagne, dine on a delicious brunch, and glide through the crystal clear surrounding waters.  This two-hour day sail features complimentary mimosas, Bloody Marys, champagne, wine, beer, soft drinks, and water. Brunch includes spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, and other delicious treats! (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: Schooner America 2.0   Cost: Adult $116 | Child $48

Key West Brunch Sail

Easter Brunch Sail aboard Schooner America 2.0

Enjoy your Easter morning aboard Key West’s most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. 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 complimentary mimosas, Bloody Marys, champagne, wine, beer, soft drinks, and water. Brunch is provided, including spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, 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!

  Duration: 2 hrs   Boat: Schooner America 2.0   Cost: Adult $96