We Found These Experiences For You (119)
Sailing and Florida
Private Party Sail - Catamaran Echo 2 or Echo 3
2hr • Groups from 4 to 25 guests! • For custom dates / times TEXT 305-304-2633
Get ready for a festive two-hour private sailing party on a smooth Echo catamaran around Key West. Enjoy bottomless Chandon Brut, a selection of eight premium wines, ice-cold beers and hard seltzers, plus soft drinks and bottled water while you relax on shaded seating or the trampoline deck. A champagne-inspired ...
Key West
2 hours
Kid-Friendly, Private Tours
Boat Tour, Catamaran, Sailing, Sightseeing Tour, Water Activities
Catamaran Echo
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New Year's Eve Dockside Bash on Schooner America 2.0
From $296 + tax/gratuity • 3 Hrs
Join us aboard America 2.0 for a wonderful New Year's Eve Bash! Enjoy this timeless celebration on the most exclusive boat in the Historic Bight, and experience VIP dockside access to the famous Schooner Wharf Bar "Lowering of the Pirate Wench" from the rig of Schooner America 2.0! This ...
Key West
3 Hours
Sailing
Classic Harbor Line - Key West
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New Year's Eve Champagne Sunset Sail Aboard Schooner America 2.0
$124 Adults • 2 hours
Enjoy your New Year's Eve sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. ...
Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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New Year's Day Champagne Sunset Sail Aboard Schooner America 2.0
From $124 Adults • 2 hrs
Enjoy your New Year's Day sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. ...
Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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Wreckers Race aboard Schooner America 2.0
From $108 • 3 hrs
All hands on deck! Sail aboard the Schooner America 2.0 for the monthly Schooner Wharf Bar Wrecker's Cup Race! Back in the days of the yore, pirate ships from afar often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the scallywags in Key West heard there ...
Key West
3 hours
Sailing
Classic Harbor Line - Key West
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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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Christmas Brunch Sail aboard Schooner America 2.0
Enjoy your morning with us in Key West in style! • 2.5 Hours • From $169 per adult
Enjoy your holiday in Key West aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. 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 morning ...
Key West
2,5 Hours
Sailing
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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Christmas Eve Sunset Sail Aboard Schooner America 2.0
$124 Adults • 2 hours
Enjoy your Christmas Eve sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. This ...
Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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Cocoa and Carols: Live Christmas Music Cruise aboard Schooner America 2.0
December 20th-24th only!
Happy Holidays from Classic Harbor Line! 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 in full holiday decor for a 1.5-hour cruise in Key ...
Key West
1.5 Hours
Boat Tour, Sailing
Classic Harbor Line - Key West
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Christmas Day Sunset Sail Aboard Schooner America 2.0
$124 Adults | 2 hrs
Enjoy your Christmas Day sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. This ...
Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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Powerboat Races
7 Hours • All Ages • Mimosas, Beer, Wine, Snacks & Lunch Included
Watch the Powerboat Races from the water with Danger Charters for an exciting all-day experience in Key West. Guests are welcomed in the morning with fresh mimosas and breakfast pastries before your captain sets a course for a prime race-viewing location. Throughout the day, enjoy unlimited beer, wine, ...
Key West
7 hours
Sailing
Danger Charters
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Morning Sail, Snorkel & Kayak Excursion
4.5 Hours • All Ages • Sodas, beer, wine & snacks included
Start your day with the ultimate Sail, Snorkel, and Kayak Excursion, a 4.5-hour journey on our shallow draft schooners! Glide through mangrove channels on kayaks; snorkel in crystal, calm waters; and unwind on deck with the refreshing Florida breeze. Our tours include top-notch gear, ensuring a seamless ...
Key West
4.5
Kayak, Sailing, Snorkeling
Danger Charters
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Premium Day Sail, Snorkel, & Kayak with Lunch
LIKELY TO SELL OUT! • 6.5 Hours • All Ages • Sodas, beer, wine, snacks and lunch included
The Full Day Excursion The Full Day Excursion is the perfect trip for you all that love being out on the water. It’s got everything the half day does and then some. We will spend plenty of time snorkeling as well as kayaking around one of the mangrove islands. Weather permitting we will stop at an ...
Key West
6.5 Hours
Kayak, Sailing, Snorkeling
Danger Charters
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Afternoon Sail, Snorkel, Kayak & Sunset Excursion
4.5 Hours • All Ages • Sodas, beer, wine & snacks included
The Afternoon Sail, Snorkel, Kayak & Sunset Trip combines sailing, snorkeling, and kayaking. One of the best parts? You'll stay out to watch a famous Key West sunset! You'll sail on an authentic schooner into the calm, protected waters of the Key West National Wildlife Refuge - a remote ...
Key West
4.5
Kayak, Sailing, Snorkeling
Danger Charters
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Private Harbor Cruise Day Sail
Accommodates up to 26 guests • Drinks, snacks, and gratuity included
Set sail aboard one of our historic schooners for a customizable 1.5-hour day sail through the beautiful waters of Key West! This relaxed private charter is perfect for birthdays, reunions, graduations, engagements, company outings, and other special occasions with your favorite crew. Your charter includes ...
Key West
1.5 hours
Private Tours
Boat Tour, Sailing
Danger Charters
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Fourth of July Fireworks Trip
2 Hours • All Ages • Departs at 8pm • Wine, beer, and hors d'oeuvres included
Skip the crowds and watch the Fourth of July fireworks from the water aboard a 65-foot schooner in Key West. This festive holiday cruise with Danger Charters gives guests a front-row vantage point for the fireworks show in a relaxed, memorable setting on the water. Guests can enjoy a selection of beer ...
Key West
2 hours
Sailing
Danger Charters
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4th of July Sunset Sail and Fireworks combo
Small Group
Celebrate the Fourth of July aboard the original Wind & Wine Sunset Sail by Danger Charters, a special evening on the water that combines a classic Key West sunset with an unforgettable fireworks finale. Sail aboard an authentic schooner and settle into a relaxed, intimate atmosphere as the evening ...
Key West
3.5 hours
Boat Tour, Sailing, Sunset Sail
Danger Charters
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Sunset Sail
2 Hour Private Charter
Enjoy a peaceful cruise through the bay at SkyBeach Resort Marina as the sun dips below the horizon. Glide along calm intracoastal waterways that set the scene for unforgettable colors on the water while guides point out playful wild dolphins. This relaxed outing is perfect for guests who want to unwind, ...
St Petersburg
Private Tours
Boat Rental, Boat Tour, Sailing
Florida Sail
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Dolphin Spotting Sail
2 Hour Private Charter
Set sail along the bay and witness the captivating city skyline, multi-million dollar waterfront mansions, and diverse wildlife. Playful dolphins often make appearances, accompanied by pelicans, and on rare occasions, you might spot manatees. This sail is the perfect opportunity to connect with nature, ...
St Petersburg
Private Tours
Boat Rental, Boat Tour, Dolphin, Sailing
Florida Sail
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Half-Day Sail
4 Hour Private Charter
Escape the hustle and bustle with our most popular sailing trip-the half day sail! This charter kicks off with a leisurely sail along the intercoastal waterways to one of the best local shelling islands in Florida. Once at Shell Key, you'll have time to swim, snorkel, and look for shells before ...
St Petersburg
Private Tours
Boat Rental, Boat Tour, Sailing
Florida Sail
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Full-Day Sail
8 Hour Private Charter
Embark on a customized sailing adventure and choose your destination. Egmont Key, Anna Maria, or Shell Key. Opt for Egmont Key to explore a historic island, home to gopher tortoises, remains of Fort Dade, and secluded beaches. Choose Anna Maria for a charming coastal town with picturesque surroundings. ...
Miami, St Petersburg
Private Tours
Boat Rental, Boat Tour, Sailing
Florida Sail
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Sunday Funday Swim & Brunch
All ages • Summer - October • Bottomless Mimosas, Bloody Mary's, and Swimming Fun! • 3 Hours
Join us for Summer Sunday Funday on the Argo Navis! Guests enjoy a light brunch, bottomless mimosas, bloody marys, house made cocktails along with Miller Lite, spiked seltzers, Florida craft brews, and plenty of Alcohol-Free options! During our first hour, we sail along the historic Key West shoreline, ...
Key West
3 hours
Sailing
Hindu Charters LLC - Argo Navis
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Key West Pride Brunch Sail & Swim
Ages 21+ • June 5th • Official Event of Key West Pride • 3 Hours • Cozzie Contest!
Duration 3 hours About Come out sailing in support of Gay Key West and Key West Pride Week! We're hosting a brunch, sail, & swim at this festive fundraiser ~ a portion of every ticket sold goes back to Gay Key West! Come in your favorite color or representation of the rainbow to celebrate this ...
Key West
LGBTQ-Friendly
Sailing
Hindu Charters LLC - Argo Navis
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Viewing 1 to 25 of 119 Experiences