Key West JanuaryCruises and Events

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.

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!

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!

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!

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!

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.

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!

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!

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.