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Key West MayCruises and Events

Key West Champagne Sunset Sail on Schooner America 2.0

Experience Key West's Best: Unmatched SunsetViews Aboard the 105-foot Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $108 to $124 Adult, $54 to $74 Children (Ages 2-12), Infants Free
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There is simply nothing better than sailing at sunset in Key West. So, why experience it on anything other than the best Key West sunset cruise aboard the Schooner America 2.0? Glide through emerald green waters with the wind in your hair and the sea breeze on your face. Enjoy a Key West romantic sunset sail in an elegant and relaxing atmosphere, complete with comfortable bench seating and refreshments. Witness the breathtaking Key West sunset, renowned for its vibrant colors, and keep an eye out for playful dolphins and the elusive Key West “Green Flash!” This picturesque and sunset boat tour is the perfect way to end your day in Key West and create unforgettable memories.

Mother’s Day Brunch Sail aboard Schooner America 2.0

Enjoy a Mother's Day Brunch Sail aboard the Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: Starting at $84 Adult, $48 Children
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Enjoy your Mother's Day aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. This is a Key West Mother's Day Brunch Cruise you don't want to miss! 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 two complimentary alcoholic beverages. Brunch is provided, including bagels and pastries, meats and cheeses, smoked salmon, quiche, 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!

Classic Day Sail aboard Schooner America 2.0

Enjoy an afternoon on the water for a Schooner America 2.0 day sail in Key West!
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $56 Adults, Kids Sail Free!
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Looking to get out on the water? Consider this fun Florida Keys Day Sail! A Key West sightseeing cruise aboard the Schooner America 2.0 is the best way to experience our beautiful waters. This Key West day sail is the perfect family activity too! Sail past Fort Zachary Taylor, Mallory Square and then head out into the emerald green waters that Key West has to offer. Light narration provided by the captain and crew will orient you to all the sights visible from the waterfront, and you’ll learn about the unique ecology and history of the beautiful Florida Keys! On this Key West sailing adventure, there is even a chance that our day sail will turn into a dolphin watching cruise! So, bring your family and friends and join our attentive crew for this adventurous day sail that completes the Key West experience in comfort and style!

Key West Full Moon Sail aboard Schooner America 2.0

Sail by moonlight on this nighttime adventure aboard the 105 ft Schooner America 2.0
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $64 Adult
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This Key West moonlight sail is perfect for a romantic evening on the water, sharing a fun evening with friends, winding down after a long day of sightseeing. If night sailing in Key West is on your bucket list, we’ve got you covered with this full moon boat tour!

This special full moon cruise in Key West is only offered for a limited time every month!

Looking for other ways to get out on the water after dark? Consider our Key West Stargazing Sail or our Starry Night Astronomer-Guided Stargazing Sail!

Haunted Seas: Nautical Superstitions and Ghost Stories on Schooner America 2.0

Step aboard Schooner America 2.0 for an eerie evening sail, where haunting nautical tales come to life under the moonlit Key West sky.
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $68 General Admission
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Get your ghost hunting hats on! Join us aboard for a haunted boat tour in Key West. This is a nautical Key West ghost tour aboard the Schooner America 2.0 that will give you the eerie chills. Set sail with us in the mysterious waters of Key West and enjoy an unforgettable evening of ghostly tales and maritime lore! Sail with us through the night and enjoy a beverage in hand as you learn the rich haunted history of this famous island. This haunted tour in Key West is by far the most unique way to experience both sailing and history with a spooky twist!

Interested in more ways to get out on the water after dark? Try our unguided Key West Stargazing Sail or Full Moon Sail!

Starry Night: Astronomer Guided Stargazing Cruise Aboard Schooner America 2.0

Unveil the wonders of our solar system on a Key West Stargazing cruise for a guided stargazing tour of the night sky!
Duration: 1.75 hrs
Boat: Schooner America 2.0
Cost: $82 General Admission
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Experience the serenity of Key West night sailing aboard the Schooner America 2.0 for a Key West stargazing cruise. The dark Key West skies will reveal a canvas of stars and celestial phenomena on this starry night tour. Our knowledgeable astronomer offers live narration about the constellations, planets, galaxies, and shooting stars. Whether you're an astronomy enthusiast, seeking quiet reflection, or seeking the perfect family night activity, this night sky tour aboard the Schooner America 2.0 promises a serene and captivating experience while stargazing beneath the night sky. This Key West narrated cruise features a bar and snacks available for purchase (for adults 21+). Interested in more ways to get out on the water after dark? Try our unguided Key West Stargazing Sail or Full Moon Sail!

Key West Private Morning Charter on Schooner America 2.0

Enjoy a Key West Private Morning Charter aboard Key West's most elegant sailboat, the 105-foot, Schooner America 2.0
Duration: 1.5 hrs +
Boat: Schooner America 2.0
Cost: Contact for Pricing
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Let us whisk you and yours away on a glorious morning cruise across the beautiful waters of Key West on your own private yacht! This 1.5+ hour private sailing experience aboard the Schooner America 2.0 grants you all the luxuries of yachting on your own private sailing yacht without the huge price tag, or the maintenance! This is the perfect way to start your day of sightseeing in Key West! Just sit back and relax, surrounded by your loved ones, friends, or co-workers, and let us take care of the rest.

Key West Stargazing Cruise Aboard Schooner America 2.0

Schooner America 2.0 stargazing is the perfect Key West family night activity while you are visiting town
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $64 General Admission
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Experience the serenity of night sailing aboard the 105-foot Schooner America 2.0 for a Key West Stargazing Cruise. Away from land, the dark Key West skies reveal a canvas of stars and celestial phenomena. Whether you're an astronomy enthusiast or seeking quiet reflection, stargazing aboard the Schooner America 2.0 promises a serene and captivating experience beneath the night sky. This is the perfect sail to unwind after a long day in Key West. Ranked one of our most peaceful sails!

Mamas & Mimosas: Mother’s Day Mimosa Sail on Schooner America 2.0

Celebrate Mother's Day in style aboard the Schooner America 2.0 on a Key West sailing cruise designed to pamper and indulge.
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $64 Adult, FREE for Moms
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Toast to mom's special day with a refreshing Mother's Day mimosa upon boarding, then embark on a leisurely journey along the coast of Key West. Whether you're relaxing on deck with a glass of champagne in hand or taking a turn at the helm, this special Key West Mother’s Day event promises to create cherished memories for mom! Treat her (or yourself!) to a sailboat ride aboard the Schooner America 2.0 for this special Mother’s Day event, where every moment aboard is a celebration of motherhood and love. Soak up the morning sunshine with your family on this Key West boat ride experience!

Take to the water on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in 1851, and enjoy a top rated Key West sightseeing cruise.

Key West Sailing in May aboard Schooner America 2.0

As summer begins to heat up, Key West comes alive with a myriad of exciting activities and events. Check out all the best things to do in Key West aboard Schooner America 2.0! May presents a unique opportunity for sailing enthusiasts and visitors alike, as it’s your final chance to experience the beauty of Key West aboard the Schooner America 2.0 before the boat returns to New York for the summer season. This is your moment to immerse yourself in the quintessential Key West sailing experience for day sails and sightseeing boat rides along the waterfront to romantic sunset sails that are perfect for date night – our Key West events may be the best decision you make all month!  

Don’t miss out on our popular Key West Sunset Sails, where you can take in the breathtaking colors of the sun setting over the horizon, or indulge and join us on one of our relaxing afternoon Day Sails to soak up the sun. For a truly memorable experience, join us for our special May event—the Mamas and Mimosas Mother’s Day Sail. This unique Mother’s Day cruise is a perfect way to celebrate the special women in your life with a delightful combination of mimosas and stunning views.

With so many fantastic Key West boat tours available, sailing aboard the Schooner America 2.0  will provide an unforgettable experience, combining professional service with unparalleled scenery. Don’t let this Key West sailing opportunity slip away—make the most of your time while in town and create lasting memories with us!

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Our Reviews

“Great sail! Crew was excellent just a great way to spend a relaxing afternoon in Key West! I Highly recommend this experience!”

– Very Happy Passenger

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