We Found These Experiences For You (23)
Day Sail and Florida
Classic Day Sail Aboard Schooner America 2.0
$56 Adults - Kids Under 12 Sail Free!
Enjoy an afternoon on the water aboard Schooner America 2.0, namesake of the first sailboat to win the 1851 America's Cup Race. The stunning Schooner America 2.0 is a 105-foot sailboat built in Albany, NY in 2011. She is the namesake of the first schooner to win the 1851 America's Cup Race. ...
Key West
1.5 Hours
Adirondack Sailing, Boat Tour, Cruise / Large Boat, Day Sail, Dolphin, Sailing, Sunset Sail, Water Activities, Yacht Charter
Classic Harbor Line - Key West
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Full Moon Sail Aboard Schooner America 2.0
From $64 • 1.5 hrs
Experience the serenity of Key West night sailing aboard the 105-foot Schooner America 2.0. 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 ...
Key West
1.5
Adirondack Sailing, Boat Tour, Cruise / Large Boat, Day Sail, Party Boat, Sailing, Water Activities, Yacht Charter
Classic Harbor Line - Key West
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Key West Lighted Boat Parade aboard America 2.0
From $104 • 3 Hours
Join us for Key West's Annual Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the fastest, most elegant schooner, the brand new eco-friendly, America 2.0 as we parade through the Bight and Harbor of Key West! She'll be fully decorated in Holiday decor with up to 30 other ...
Key West
3 Hours
Adirondack Sailing, Boat Cruise, Boat Tour, Booze Cruise, Cruise / Large Boat, Day Sail, Evening Cruise, Sailing, Sunset Cruise, Sunset Sail, Water Activities, Yacht Charter
Classic Harbor Line - Key West
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Full Day Sail
Private Charter · 8 Hour Sail · Max 6 People · Key West Fun!
Spend The Day On The Water! Duration 8 Hours About There is simply NOTHING available like this in Key West! This is a full 8 hours at sea! Enjoy a relaxing excursion of sailing, snorkeling, SCUBA diving and just about any adventure you can conjure, all aboard our amazing 42" or 60"sailing catamaran. ...
Key West
Private Tours
Boat Tour, Catamaran, Day Sail, Sailing, SCUBA, Snorkeling
Restless Native Charters
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Epic Sail
12 hours · 6 guests · See the Keys by SEA!
Enjoy an Epic Day in the Keys! maximum 6 people Duration 12 Hours About With this package we are excited to share with you some parts of Key West that you cannot get to on a simple day sail. Enjoy the open ocean and some private escapes as we stretch our sea legs. Our adventure begins early-ish and we ...
Key West
Private Tours
Boat Tour, Day Sail, Sailing, SCUBA
Restless Native Charters
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Overnight Expedition
Private Charter · Spend the Night On the Water! · Max 6 people
Duration 2 Days, One Night Overnight Sailing Trip! This certainly qualifies as an Epic Adventure! Grab your favorite travel/adventure partner and set sail with us to the famous Marquesas and snorkel, and live on the water as we take care of your every need along the way! Its a full day on board with ...
Key West
Private Tours
Beer Tour, Boat Tour, Day Sail, Dinner Boat, Food Tour, Private Wine Tour, Sailing, SCUBA, Skydive, Snorkeling, Sunset Sail, Wine
Restless Native Charters
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Half Day Sail
$1,400 to $2,400 · 4 hours · Lovely day at sea with six guests!
Delightful Afternoon on the Water! maximum six people Duration Four Hours About Are you ready to set sail on the open ocean, wind in your hair, drink in hand? Our unique "Day Sail" is ready for you to swim, snorkel or just play on some floaties! We depart to some of our favorite places to sail, ...
Key West
Boat Tour, Day Sail, Sailing, SCUBA, Snorkeling
Restless Native Charters
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3/4 Day Sail
6 Hour Sail · Max 6 People Private Charter
Enjoy a 6 Hour Sail! Duration 6 Hours About This amazing day on the water begins early at 9:00 am so that we have ample time to show you the incredible reefs of Key West if you'd like to snorkel, or enjoy the barrier islands and mangroves that surround the region offering abundant wildlife, unspoiled ...
Key West
Private Tours
Boat Tour, Day Sail, Sailing, SCUBA, Snorkeling
Restless Native Charters
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Sunset Sail
For all ages! • 3 Hours • Chartered Yacht
Choose between our fleet of Luxury Yachts Duration 3 Hours Capacity Up to 12 guests on any of the boats in our fleet About Step away from the crowds of Key West to enjoy your own private sunset cruise aboard one of our beautiful catamarans. Our 3-hour sunset sail allows plenty of time to enjoy the water, ...
Key West
Private Tours
Boat Cruise, Boat Rental, Boat Tour, Catamaran, Cruise / Large Boat, Day Sail, Sailing, Snorkeling, Sunset Cruise, Sunset Sail
Sail Away Key West
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4hr Private Dolphin Watch / Snorkel Sail
4hr • Up to 12 Guests • Sail and Snorkel The Keys
Fun above and below the waterline! Set Sail as we navigate under sail for a truly Eco friendly adventure! We will use our expertise to sail towards the Dolphin playground and then to our "backcountry" snorkeling destination. Each sail and destination is different depending on the days conditions ...
Key West
Private Tours
Boat Tour, Day Sail, Private Boat, Sailing, Snorkeling
Sunset Sail Key West
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Starlight Sail
1.5 hours • Up to 12 Guests • Private Charter • Stargazing Under Sail
Sailing under the stars Relax as you sail out beyond the lights and sounds of Key West and get a clear view of the spectacular nighttime sky. Gaze into the night to spot the seasonal celestial highlights as we shut the engine off and take a peaceful sail through the starlight. Duration 1.5 Hours Trip ...
Key West
Private Tours
Boat Tour, Day Sail, Private Boat, Sailing
Sunset Sail Key West
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4hr Private Snorkel Sunset Combo
4hrs • Up to 12 Guests • From $995
The best of both worlds! Enjoy a sail over to the spot where your Sunset Sail Key West captain will set the anchor for a swim call. There's a lot to see, from back country sponge beds and coral nurseries to lobster and reef fish to mangrove wildlife. Your view will depend on the day's weather ...
Key West
Private Tours
Boat Tour, Day Sail, Private Boat, Sailing, Snorkeling, Sunset Sail
Sunset Sail Key West
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3hr Private Chillout Lilypad Sail
3hr • Up to 12 Guests • Private Charter • From $695 •Sail And Swim Call
A one-of-a-kind trip that really celebrates Keys living! A short sail with Sunset Sail Key West brings us to a sheltered spot where we'll anchor in some shallow water and unroll the lily pad. This giant 6x12ft raft is the perfect watertoy, allowing you to lounge in the sun but stay cool in the sea! ...
Key West
Private Tours
Boat Tour, Day Sail, Private Boat, Rafting, Sailing
Sunset Sail Key West
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2hr Proposal Private Sunset Sail
2hrs • Perfect Romance
"And they sailed away into the sunset forever." Now's your moment! With the golden sun kissing the horizon, soft waves lapping against the hull, a bottle of champagne ready on ice, and crew secretly standing by with your camera for photos and videos, it's time to get down on one knee. ...
Key West
Private Tours
Boat Tour, Day Sail, Private Boat, Sailing, Sunset Sail
Sunset Sail Key West
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Historic Schooner Day Sail From Downtown Key West
2hrs Afternoon Yachting
Sail away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton "When the war is over, and if I live through it, Bea and I are going to sail her around the world." When And If is the peacetime dream of an American war hero with her greatest destiny as yet unfulfilled. ...
Key West
Pickup Available
Boat Tour, Day Sail, Sailing
Sunset Sail Key West
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Private Key West Harbor Sunset Sail
2 hours • Up to 12 Guests
Private, personal and elegant sunset charter At Sunset Sail Key West we bring you the perfect end to an island day; capture the magic of it all from the deck of your own private tropical sailboat. Sunset Sail Key West boasts a fleet of unique classic sailboats and we strive to revive the romance and ...
Key West
Private Tours
Boat Tour, Day Sail, Harbor Tour, Private Boat, Sailing, Sunset Sail
Sunset Sail Key West
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Private Historic Schooner Day Sail From Downtown Key West
2 Hours • Classic Schooner Yacht Day Sailing
Sail away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton Duration 2 hours "When the war is over, and if I live through it, Bea and I are going to sail her around the world." When And If is the peacetime dream of an American war hero with her greatest destiny as ...
Key West
Private Tours
Boat Tour, Cruise / Large Boat, Day Sail, Sailing, Yacht Charter
Sunset Sail Key West
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1.5hr Private Key West Harbor Day Sail
1.5hrs • Up to 12 Guests • From $395
A perfect daysailing taster Catch that warm keys breeze with Sunset Sail Key West as you head for a sun-soaked daysail out of Downtown Key West. Your Sunset Sail Key West captain and crew will raise sail and shut off the engine so you can relax and enjoy the serenity of life under sail. Take a turn at ...
Key West
Private Tours
Boat Tour, Day Sail, Private Boat, Sailing
Sunset Sail Key West
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Private Historic Schooner Sunset Sail From Downtown Key West
Private Charter Sunset Sail on Classic Schooner Yacht
Sail away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton Duration 2 hours "When the war is over, and if I live through it, Bea and I are going to sail her around the world." When And If is the peacetime dream of an American war hero with her greatest destiny as ...
Key West
Private Tours
Boat Tour, Cruise / Large Boat, Day Sail, Sailing, Sunset Sail, Yacht Charter
Sunset Sail Key West
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Smathers Beach Day Pass w/ Parasail
Parasail and ALL the beach toys!
Join us for Key West's all inclusive watersports package. This pass includes unlimited kayak, paddleboard, hobie cat rentals and a parasail flight. Spend the ultimate day at the beach with the Smathers Beach Pass.
Key West
All Day
Boat Tour, Day Sail, Kayak, Parasail, Sailing
Sunset Watersports
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Viewing 1 to 20 of 23 Experiences