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RomanticCruises & Packages

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.

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!

Follow the Mermaid

Join us aboard the Schooner America 2.0 for an evening of entertainment for the Follow the Mermaid show!
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: Starts at $89
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Join us for this special Key West speakeasy cruise featuring live aerial, burlesque, and delicious cocktails after-hours aboard Schooner America 2.0! Step aboard for an immersive speakeasy experience offering a curated mix of Burlesque, Acrobatics, Aerial, and more aboard the Schooner America 2.0 in Key West Harbor. This exceptional experience is brought to you by the Follow the Rabbit Bar in collaboration with Classic Harbor Line. Experience a truly unique evening on the water aboard the Schooner America 2.0 that will be an unforgettable experience!

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!

Live Jazz Night Sail Aboard Schooner America 2.0

Join us for a festive 1.5-hour Live Jazz Sail on the stunning 105-foot Schooner America 2.0 in Key West harbor
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $68 Adult, FREE for Ages 0-12 on select dates
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Join us aboard the stunning schooner America 2.0 for a unique Key West experience. Aboard our beautiful 105-foot Schooner America 2.0 enjoy the sounds of jazz as you sail through the night. This 1.5-hour cruise in Key West harbor is sure to be a lasting memory! Sit back and enjoy quality time with your loved one or friends. Schooner America 2.0 features the best in comfort- teak decks, mahogany-trimmings, and a soaring rig! Sit back and take a ride on this schooner while you enjoy the evening with your family and friends. Join our courteous and professional crew for this evening celebration cruise that will highlight your Key West experience!

Valentine’s Day Champagne Sunset Sail on Schooner America 2.0

Take to the water and fall in love all over again on this romantic Valentine’s Day cruise in Key West!
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $158 Adults
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Experience romance at its finest aboard the Schooner America 2.0 with our exclusive Key West Valentine’s Day Cruise. As the sun begins to set on this romantic couples cruise, embark on a magical journey along the picturesque coast of Key West surrounded by the beauty of the open sea. During your Valentine’s Day getaway, you and your loved one will enjoy a delicious bottle of French champagne served in beautifully etched souvenir glass flutes. You’ll dine on yummy passed hors d’oeuvres and enjoy a special dessert for two. Set sail on this Key West Valentine’s Day experience designed for couples where love is in the air.

Take to the water in Key West and fall in love all over again!

The best way to spark some romance is with a romantic sunset cruise in Key West.  Are you looking for the perfect proposal cruise setting in Key West? Maybe, you’d like to renew your vows on a special anniversary cruise after a lifetime of memories. Or perhaps, you’re just looking to REALLY impress your first date on a romantic sunset cruise in Key West… Well, it doesn’t get much more romantic than sailing aboard the Schooner America 2.0!  Whether it is a sunset harbor cruise on a Key West Champagne Sunset Sail, Full Moon Sail or one of our special romantic packages tailored just for you and your loved one, we’ll help you create an unforgettable sailing experience and memories to cherish for a lifetime. Looking for something more intimate or a way to celebrate a proposal or anniversary with close family and friends? Consider a Key West private sunset cruise aboard Schooner America 2.0!

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