Key West, FL
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Day Sailing

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You love sailing! We do too! Join us aboard the Schooner America 2.0 and cruise with us for a classic Key West Day Sail!  Soak in the afternoon sun as you sail with us aboard this stunning yacht. On this Key West day sail we will have 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 wildlife and watch the 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 Key West 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 $56 | Child $26

Schooner America 2.0 sailing in the morning sunlight for a Key West Mimosa Sail

Private Morning Sail on Schooner America 2.0

Step aboard the stunning America 2.0 for a Key West Morning Charter. 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. Options to extend your trip are available. Charter includes soda, juice, and water. Bar and food packages are available upon request. (Call us directly to save 6% online processing fee)

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

Stern of the schooner America 2.0 with the sails raised and the Captain Turned around waving while sailing for a 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!

One round of beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase. Purchase a Beverage Package during the booking process, or additional drinks for credit card purchase while on board. (Call us directly to save 6% online processing fee)

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

Key West Brunch Sail aboard the Schooner America 2.0 with guests in the cockpit enjoying food

Christmas Day Brunch Sail aboard Schooner America 2.0

Are you dreaming of a crystal clear, blue Christmas? Then, spend your Christmas morning aboard the Schooner America 2.0 for a brunch sail that you and your loved ones will never forget! Start your day with complimentary mimosas, bloody mary’s, or champagne as you sail into the Christmas spirit. This two-hour sail includes a fully-catered brunch that will be sure to help you start Christmas day the right way! On this peaceful holiday sail, you can relax to the natural sounds of the wind and waves, and appreciate the beauty of Key West during the holiday season. (Call us directly to save 6% online processing fee)

  Duration: 2.5 hrs   Boat: Schooner America 2.0   Cost: Adult $136 | Child $63

Solar Eclipse image of sun with a moon in front of it

Partial Solar Eclipse Viewing Cruise Aboard Schooner America 2.0

April 8th 2024! Sail through the Key West waters aboard one of Key West’s most stunning modern sailboats, the 105 ft Schooner America 2.0. This special sail is only offered once every 241 years! Join us for the partial solar eclipse aboard the Schooner America 2.0.  Schooner America 2.0 features teak decks, mahogany-trimmings, and just under 3600 square feet of canvas! Sit back and enjoy this magical moment.  A solar eclipse happens when the Moon passes between the Sun and Earth, completely blocking the face of the Sun. We will provide you with protective eyewear as it’s important to never look directly at the sun without proper eye protection.

  Duration: 1.5 hrs   Boat: Schooner America 2.0   Cost: $64

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