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Nighttime Cruises

Guests aboard the schooner America 2.0 at night.

Key West Nighttime Cruises

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!
https://fareharbor.com/embeds/book/sail-keywest/items/26523/?full-items=yes&flow=5116

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!
https://fareharbor.com/embeds/book/sail-keywest/items/610253/?full-items=yes&flow=1252027

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!
https://fareharbor.com/embeds/book/sail-keywest/items/522626/?full-items=yes&flow=5116

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!
https://fareharbor.com/embeds/book/sail-keywest/items/526630/?full-items=yes&flow=5116

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!
https://fareharbor.com/embeds/book/sail-keywest/items/615448/?full-items=yes&flow=1252027

Enjoy an astronomer guided stargazing cruise aboard Schooner America 2.0

Join us for one of our Key West nighttime cruises! Experience an unforgettable sail on the water in Key West at night! Schooner America 2.0 has a variety of evening cruises that are perfect for an after dinner adventure. Whether you want to have the perfect date night with a stargazing or full moon sail or go out with friends for a Key West ghost tour, we have the sailing experience for you. This is one of the best things to do in Key West to the full island experience at night!

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Date
Night
Family
Friendly
Sunset
Sails
Day
Sails
Christmas/
New Year's
Stargazing
Sails
Full-Moon
Sails
Specialty
Cruises
Sailboat
Racing
Holiday
Private
Charter

Christmas/New Year’s

Christmas / New Year’s Events and Cruises

New Year’s Day Champagne Sunset Sail Aboard Schooner America 2.0

Start your year off right with an unforgettable New Year’s Day Champagne sunset sail on the Schooner America 2.0 in Key West
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
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Embark on an unforgettable New Year’s Day sunset sail aboard the Schooner America 2.0. Drift through the enchanting waters of Key West with the wind in your hair and the sea breeze on your face. Revel in an elegant and relaxing atmosphere as our crew serves delectable refreshments, including beer, wine, champagne, and hors d’oeuvres. Marvel at the breathtaking Key West sunset, celebrated for its vibrant hues and the elusive “Green Flash,” and watch for playful dolphins. Conclude your evening with a special champagne toast and take home a souvenir champagne flute to remember your perfect vacation. This picturesque New Year’s Day celebration is the ultimate way to begin your year in Key West!

The Schooner America 2.0, constructed in 2011, boasts elegant teak decks, comfortable seating, and a vast 3,600 square feet of canvas. Unwind and enjoy the final sunset sail of the year as she gracefully navigates the turquoise waters of Key West.
https://fareharbor.com/embeds/book/sail-keywest/items/555004/?full-items=yes

New Year’s Eve Champagne Sunset Sail Aboard Schooner America 2.0

Celebrate with a memorable New Year's Eve sunset sail Key West style aboard the Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
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Start your Key West New Year’s eve celebration off with a sunset sail. Experience an unforgettable Key West New Year’s Eve sunset cruise aboard the Schooner America 2.0! Get into the holiday spirit with your friends or family as you sail through the beautiful waters of Key West with the wind in your hair and the sea breeze on your face. Enjoy an elegant and relaxing atmosphere while our crew serves you delicious refreshments, including beer, wine, champagne, and hors d’oeuvres on this Key West New Year’s Eve sunset cruise. Witness the breathtaking Key West sunset, renowned for its vibrant colors and the elusive “Green Flash,” and keep an eye out for playful dolphins. Finally, finish your sunset sail with a special champagne toast and a souvenir champagne flute to take home and remember your perfect vacation. This picturesque New Year’s Eve celebration is the perfect way to end your year in Key West!
https://fareharbor.com/embeds/book/sail-keywest/items/426904/?full-items=yes&flow=5116

Cocoa and Carols Christmas Holiday Lights Cruise Aboard Schooner America 2.0

Join us for a festive 1.5-hour Christmas cruise on the decorated 105-foot Schooner America 2.0 in Key West harbor
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $72 to $84 Adult, FREE for Ages 0-12 on select dates
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Please join us for this special Key West warm and cozy holiday cruise tailored for friends, family, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 decorated in CHristmas lights and other fun holiday decor for a 1.5-hour cruise in Key West harbor while we listen to some of our favorite Christmas hits! Delicious Hot cocoa, cookies, and other treats for all our guests are included! Sit back and enjoy your Christmas in Key West on this family holiday cruise! America 2.0 features the best in comfort- teak decks, mahogany-trimmings, and a soaring rig! Sit back and take a ride on this decorated schooner while you enjoy the festivities of the evening with your family and friends. Join our courteous and professional crew for this evening celebration cruise that will highlight your Key West Christmas experience!
https://fareharbor.com/embeds/book/sail-keywest/items/515346/?full-items=yes&flow=no

Dockside New Year’s Eve Party Aboard Schooner America 2.0

Experience the ultimate New Year's Eve celebration, with this exclusive event in Key West aboard the Schooner America 2.0
Duration: 3 hrs
Boat: Schooner America 2.0
Cost: $256 Adults
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Prepare to be dazzled as you join fellow guests for the ultimate Key West New Year's Eve party. Enjoy VIP dockside access to the famous Schooner Wharf Bar "Lowering of the Pirate Wench" from the rig of Schooner America 2.0! From the moment you step onto the boat for this fun Key West dockside event, the Schooner America 2.0 provides the perfect backdrop for revelry, with spacious decks offering panoramic views of the harbor as your party into the night.This special '21 and older' New Year’s Eve event features complimentary delicious hors d' oeuvres and a full bar. Gather with friends and join our courteous and professional crew for this late night Key West New Year’s Eve boat party that will be the highlight of your Key West experience! This is a special New Year’s Eve celebration to ring in the New Year as the pirate wench is lowered as we countdown to midnight!
https://fareharbor.com/embeds/book/sail-keywest/items/26528/?full-items=yes&flow=34630

Christmas Eve Sunset Sail Aboard Schooner America 2.0

Enjoy a Christmas Eve sunset sail aboard Key West's most elegant sailboat, the 105-foot Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
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Experience an enchanting Christmas Eve sunset sail aboard the Schooner America 2.0, a state-of-the-art 105-foot vessel. Glide through the emerald green waters of Key West with the wind in your hair and the sea breeze on your face. Enjoy an elegant and relaxing atmosphere, complete with comfortable bench seating and refreshments, including beer, wine, champagne, and holiday themed hors d’oeuvres. Witness the breathtaking Key West sunset, renowned for its vibrant colors and the elusive “Green Flash,” and keep an eye out for playful dolphins. This picturesque sail is the perfect way to end your day in Key West, creating unforgettable holiday memories.

Built in 2011, the Schooner America 2.0 is equipped with teak decks, bench seating, and a vast 3600 square feet of canvas. Relax as she sails smoothly through the turquoise waters of Key West, offering a quintessential holiday sunset sail experience.
https://fareharbor.com/embeds/book/sail-keywest/items/426894/?full-items=yes&flow=34630

Christmas Day Sunset Sail Aboard Schooner America 2.0

Enjoy a family-friendly Christmas Day sail aboard Key West's most elegant sailboat, the 105-foot Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
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Experience a magical Christmas Day sunset sail aboard the Schooner America 2.0, a cutting-edge 105-foot vessel. Drift through the emerald waters of Key West, feeling the wind in your hair and the sea breeze on your face. Relax in an elegant atmosphere with comfortable bench seating and enjoy refreshments, including beer, wine, champagne, and holiday-themed hors d'oeuvres. Marvel at the breathtaking Key West sunset, famous for its vibrant colors and the elusive "Green Flash," and keep an eye out for playful dolphins. This picturesque sail is the perfect way to conclude your day in Key West, creating unforgettable holiday memories. Schooner America 2.0, constructed in 2011, boasts teak decks, cozy bench seating, and an impressive 3600 square feet of canvas. Enjoy a serene voyage through the turquoise green waters of Key West, gliding towards the horizon for an ideal Key West sunset sail experience.
https://fareharbor.com/embeds/book/sail-keywest/items/426899/?full-items=yes&flow=34630

Christmas Day Brunch Sail aboard Schooner America 2.0

Celebrate Christmas morning in Key West with us on a Christmas sail aboard the elegant 105-foot Schooner America 2.0
Duration: 2.5 hrs
Boat: Schooner America 2.0
Cost: $168 General Admission
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Enjoy the vibrant colors of Key West as you sip champagne, dine on a delicious brunch, and glide through crystal clear surrounding waters on one of Key West’s premiere holiday cruises. This Christmas brunch Key West-style features complimentary mimosas, bloody marys, champagne, wine, beer, soft drinks, and water. Brunch includes spiral ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, quiche, and other delicious treats! This is one of the few Christmas Day events in Key West not to be missed! Built in 2011, Schooner America 2.0 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 holiday brunch experience!
https://fareharbor.com/embeds/book/sail-keywest/items/121441/?full-items=yes&flow=34630

Key West Lighted Boat Parade aboard America 2.0

Experience the magic of the Annual Key West Lighted Boat Parade aboard the festively adorned Schooner America 2.0
Duration: 3 hrs
Boat: Schooner America 2.0
Cost: $104 Adult, $48 Children
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Join us for the Key West Annual Lighted Boat Parade aboard Schooner America 2.0! Adorned in festive lights, the America 2.0 is a dazzling spectacle on the water. Watch from our beautiful teak decks and comfortable bench seating as boats of all sizes glide through Key West harbor, illuminated in a vibrant display of colors and decorations. Onboard, enjoy the holiday atmosphere with music, refreshments, and the company of fellow revelers. As the Christmas parade progresses, marvel from a prime viewing spot onboard at the creativity and ingenuity of each boat's decorations. This enchanting event aboard Schooner America 2.0 offers a unique perspective on the holiday season and creates lasting memories for all!

Please Note: We will not be raising sails during the parade due to maneuverability.
https://fareharbor.com/embeds/book/sail-keywest/items/26529/?full-items=yes&flow=5116

Celebrate with One of Our Special

Key West Holiday Cruises!

Planning a trip to Key West during the holidays? With its lighted palm trees and historical houses decorated to the max, Key West is embracing the spirit of Christmas in all its glory during this festive season.  Celebrating the holidays in Key West aboard the Schooner America 2.0 offers a unique and enchanting experience aboard a Key West holiday boat ride that’s not to be missed. This stunning, eco-friendly yacht hosts a variety of special events, from the festive Key West Lighted Boat Parade cruise to our famous VIP New Year’s Eve Party and the lowering of the Schooner Wharf pirate wench! We also offer fun Key West Christmas events including a festive Christmas Eve Sunset Sail, Cocoa & Carols Christmas Holiday Lights Cruise during the month of December, or a Key West Christmas Day Brunch cruise, the Schooner America 2.0 combines the spirit of the season with the beauty of the sea, providing a truly magical setting for any holiday celebration. Whichever Key West holiday cruise you choose, guests can enjoy panoramic views of the island’s illuminated shoreline, savor gourmet hors d’oeuvres, and sip on delicious cocktails all while sailing through turquoise waters. Sailing aboard Schooner America 2.0 is truly an unforgettable way to experience Key West’s holiday charm.

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Date
Night
Family
Friendly
Sunset
Sails
Day
Sails
Christmas/
New Year's
Stargazing
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Full-Moon
Sails
Specialty
Cruises
Sailboat
Racing
Holiday
Private
Charter

Mother’s Day Cruise

Key West Mother’s Day Cruises

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.
https://fareharbor.com/embeds/book/sail-keywest/items/26520/?full-items=yes&flow=5116

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!
https://fareharbor.com/embeds/book/sail-keywest/items/629507/?full-items=yes&flow=1254521

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!
https://fareharbor.com/embeds/book/sail-keywest/items/26519/?full-items=yes&flow=5116

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.
https://fareharbor.com/embeds/book/sail-keywest/items/66699/?full-items=yes&flow=93526

Enjoy mother's day boat rides with our Key West sailing excursions!

Looking for some fun Mother’s Day events in Key West?  Join us for our Key West sailing cruise aboard the Schooner America 2.0! Celebrate with Mom in Key West and relax on one of our Mother’s Day Cruise departures as we sail along Key West’s waterfront. Enjoy a cold beverage onboard like a Mother’s Day mimosa or chilled glass of wine. This is the perfect Key West boat ride experience for a fun photo opportunity with Mom being Captain of the Schooner! On this fun family sailing experience enjoy good conversation and sightseeing! Make memories that will last a lifetime during this Mother’s Day Sailing Cruise our elegant schooner, America 2.0.

Whether you’re looking for a Key West morning, afternoon or Mother’s Day sunset cruise, we have the experience for you! 

During this fun Key West sailing cruise, our professional and hospitable crew will cater to your every need. Key West sailing is a magical way to capture a moment in time and our Mother’s Day events in Key West aboard Schooner America 2.0 will surely make Mom feel celebrated!

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Date
Night
Family
Friendly
Sunset
Sails
Day
Sails
Christmas/
New Year's
Stargazing
Sails
Full-Moon
Sails
Specialty
Cruises
Sailboat
Racing
Holiday
Private
Charter