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Stargazing Sails

Stargazing Sails

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 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!

Enjoy an astronomer guided stargazing cruise aboard Schooner America 2.0

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 these tours. Our knowledgeable astronomer and NASA Solar System Ambassador, Kevin Gallagher, 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.

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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.

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!

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!

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!

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.

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.

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!

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.

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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Day Sails

Key West Day Sail

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 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.

Wreckers Race aboard Schooner America 2.0

All hands on deck for this fun Key West schooner race! Set sail in Key West for the monthly Schooner Wharf Bar Wrecker's Race!
Duration: 3 hrs
Boat: Schooner America 2.0
Cost: $104 Adult, $52 Children
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Back in the days of the yore, ships from afar carrying goods often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the pirates in Key West heard there was booty to be had, they'd jump in their boats and have a good ol’ pirate ship race out to the reef. The first one there could claim the ship's cargo! Arrggh!

Today, we playfully remember this history with a sailing race out to the Sand Key Lighthouse. It all starts with a cannon firing, and then all of the schooners of Key West are on their way! The boat that gets there first "wins" the Schooner Wharf Bar Wrecker’s Cup at an evening awards ceremony. Enjoy the excitement on this Key West sailing adventure aboard Schooner America 2.0 as we race for victory! This is a fun Key West schooner race and family-friendly activity aboard Schooner America 2.0!

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!

Civil War Heritage Day Sea Battle on Schooner America 2.0

Witness history with a Civil War Heritage Day Sea Battle reanactment in one of the coolest Key West historic tours!
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $68 Adult, $34 Children
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All hands on deck! Join us on this 2-hour Key West sailing adventure aboard one of the Florida Keys most stunning sailboats, the 105-foot Schooner America 2.0. Be a part of this annual festivity as we participate in a Civil War Sea Battle (on the Union side, of course!) Soak up the sun on this Key West afternoon sightseeing boat ride! If you’re looking for a fun Civil War reenactment, this Key West family activity is a must do! But, watch out for cannon fire!

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.

2025 Blue Angels Air Show Viewing Party on Schooner America 2.0

Join us for an unforgettable viewing party aboard the Schooner America 2.0 to experience the Blue Angels Air Show!
Duration: 4.5 hrs
Boat: Schooner America 2.0
Cost: $208 Adult, $48 Children
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Join us for an unforgettable viewing party aboard the Schooner America 2.0 to experience the Blue Angels Air Show!

Looking to watch the Blue Angels Air Show? Classic Harbor Line Key West is offering a Blue Angels cruise aboard America 2.0! Your adventure includes three complimentary premium beverages and a delicious, gourmet lunch from a local bakery! As the Blue Angels take to the sky, watch their breathtaking aerial maneuvers from the best seat in the house, the open deck of our Key West yacht. Feel the excitement and energy of the show, enhanced by the comfort and elegance of our classic Key West schooner. This incredible event only occurs once every two years, so don't miss this exclusive opportunity to enjoy world-class entertainment and exceptional hospitality on the open water.

Do you love sailing? We do too!

Join us on a Schooner America 2.0 sailing tour and cruise with us for a classic Key West Day Sail or Key West sightseeing cruise!  You can even soak up the afternoon sun on one of our special day sailing tours like the Wreckers Race or a holiday brunch sail, or book Schooner America 2.0 for a private sailing charter!

No matter which afternoon day sail you choose, we are sure to have the wind in our sails as we head out into the harbor to see the sights.  Just some of the sights you’ll see along the way are  Fleming Key, Sunset Key, Sand Key Lighthouse and Fort Zachary Taylor. While this isn’t a Dolphin watching tour, you may catch a glimpse of some Key West wildlife, including dolphins, as they surf the bow of our boat. And if we are VERY lucky, we may even spot a sea turtle during your sailing tour! Schooner sailing is one of the best activities in Key West, and will make for a truly classic experience during your times in town.

Not interested in a day sail? Then, make sure to  join us on our Key West Champagne Sunset Sail, or book a private event!

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Romantic Cruises & Packages

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!

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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Sunset Sails

Key West Sunset Sails

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.

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.

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!

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.

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.

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.

Simply the best

Key West sunset cruise!

Looking for a Key West Champagne Sunset experience? Your vacation just isn’t complete without experiencing a Schooner America 2.0 sunset sail. This luxurious Key West yacht offers 360 degree sunset views, providing the perfect ambiance to watch the famous Key West sunset. Our experienced and professional crew ensure a comfortable and memorable sailing journey, catering to your every need on our Key West sunset sail.

Enjoy the smooth sailing, refreshing beverages, yummy snacks, and the wind in your hair as you cruise through the emerald green waters during your sailing experience at sunset. On this Key West Sunset boat tour you might even witness the elusive “green flash” as the sun dips below the horizon. This romantic sunset sail is not only a magical experience, but one that will keep you returning to Key West time and again for a luxury Key West sunset cruise.

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Family Friendly

Family FunBoat Tours

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!

Wreckers Race aboard Schooner America 2.0

All hands on deck for this fun Key West schooner race! Set sail in Key West for the monthly Schooner Wharf Bar Wrecker's Race!
Duration: 3 hrs
Boat: Schooner America 2.0
Cost: $104 Adult, $52 Children
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Back in the days of the yore, ships from afar carrying goods often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the pirates in Key West heard there was booty to be had, they'd jump in their boats and have a good ol’ pirate ship race out to the reef. The first one there could claim the ship's cargo! Arrggh!

Today, we playfully remember this history with a sailing race out to the Sand Key Lighthouse. It all starts with a cannon firing, and then all of the schooners of Key West are on their way! The boat that gets there first "wins" the Schooner Wharf Bar Wrecker’s Cup at an evening awards ceremony. Enjoy the excitement on this Key West sailing adventure aboard Schooner America 2.0 as we race for victory! This is a fun Key West schooner race and family-friendly activity aboard Schooner America 2.0!

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!

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!

Civil War Heritage Day Sea Battle on Schooner America 2.0

Witness history with a Civil War Heritage Day Sea Battle reanactment in one of the coolest Key West historic tours!
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $68 Adult, $34 Children
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All hands on deck! Join us on this 2-hour Key West sailing adventure aboard one of the Florida Keys most stunning sailboats, the 105-foot Schooner America 2.0. Be a part of this annual festivity as we participate in a Civil War Sea Battle (on the Union side, of course!) Soak up the sun on this Key West afternoon sightseeing boat ride! If you’re looking for a fun Civil War reenactment, this Key West family activity is a must do! But, watch out for cannon fire!

Easter Brunch Sail aboard Schooner America 2.0

Enjoy your holiday in Key West with an Easter sail aboard Schooner America 2.0!
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $84 Adult, $42 Children
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On this Key West Easter cruise aboard the Schooner America 2.0, you’ll enjoy the vibrant colors of Key West waters as you sip on mimosas, dine on a delicious brunch, and glide effortlessly along under full sail. This Easter brunch cruise is one of Key West’s premiere holiday cruises and features two alcoholic beverages (for adults 21+), soft drinks, and water. Brunch includes bagels and pastries, charcuterie, smoked salmon, quiche, crudite, and other delicious treats! This is a family cruise in Key West not to be missed!

2025 Blue Angels Air Show Viewing Party on Schooner America 2.0

Join us for an unforgettable viewing party aboard the Schooner America 2.0 to experience the Blue Angels Air Show!
Duration: 4.5 hrs
Boat: Schooner America 2.0
Cost: $208 Adult, $48 Children
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Join us for an unforgettable viewing party aboard the Schooner America 2.0 to experience the Blue Angels Air Show!

Looking to watch the Blue Angels Air Show? Classic Harbor Line Key West is offering a Blue Angels cruise aboard America 2.0! Your adventure includes three complimentary premium beverages and a delicious, gourmet lunch from a local bakery! As the Blue Angels take to the sky, watch their breathtaking aerial maneuvers from the best seat in the house, the open deck of our Key West yacht. Feel the excitement and energy of the show, enhanced by the comfort and elegance of our classic Key West schooner. This incredible event only occurs once every two years, so don't miss this exclusive opportunity to enjoy world-class entertainment and exceptional hospitality on the open water.

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.

Enjoy family friendly boat rides with our Key West sailing excursions!

Are you looking for a family boat ride while in town?  Look no further and join us on any of our family-fun boat tours in Key West aboard the stunning Schooner America 2.0. This Key West family boat ride is complete with safety features and amenities to ensure comfort for all ages. 

While this is not a dolphin watching tour, Key West is known for its beautiful wildlife and on any of our boat rides you may get a chance to spot playful dolphins and sea turtles! Enjoy a scenic boat tour of the island’s historic landmarks on our afternoon sightseeing cruise, or check out one of our holiday events, like our Cocoa and Carols cruise! Our experienced crew members will be guiding the way, and our Key West family cruises promise a blend of education, relaxation, and fun for the whole family.

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