Key West Sailing Charters & Tours
Set sail on a private sailing charter & tour in Key West and immerse yourself in the breathtaking beauty of this island paradise from the water. Whether you're enjoying a romantic sunset sail with your loved one, sipping champagne as the sun dips below the horizon, or embarking on an exciting day of exploration, Key West's calm, crystal-clear waters provide the perfect backdrop. Glide past the iconic coastline, spot dolphins playing in the waves, and explore the nearby waters, including the famous reef systems and secluded islands. These sailing tours are tailored to your preferences, ensuring an unforgettable, personalized experience that highlights the best of Key West’s natural beauty and vibrant marine life.
Featured Sailing Charters & Tours in Key West
Sorting:
Best Match
Feb 21 - Feb 27
Narrow your search
Swim Friendly
Cruise Only
Restroom
Captain Included
13-20 passenger
21-40 passenger
75+ passenger
Half Day Trip (if duration 3-6 hour)
Kid Friendly
Water Toys Available
Morning Departure (5am-11:59am)
Afternoon Departure (12pm-4:49pm)
Evening Departure (4:49-11:59pm)
86 80
Live Music Sunset Cruise with Cocktails Included
85 ratings
2 Hrs.
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book your experience today!
Read more
45
Morning Reef Snorkel and Sail in Key West with Picnic and Unlimited Mimosas
33 ratings
3 Hrs.
Imagine yourself swimming in warm tropical water with swarms of vibrant colorful fish all around you as you begin the day in the lap of luxury on an expansive 69’ sailing catamaran with a Morning Reef Snorkel and Sail in Key West, Florida with Picnic and Unlimited Mimosas. Sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Set off on this adventure and book your spot today.
Read more
117
Wind and Wine Sunset Sail
71 ratings
2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!
Read more
116
Key West Sunset Sail on America 2.0
45 ratings
2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!
Read more
52
Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas
39 ratings
3 Hrs.
Embark on an unforgettable snorkeling adventure to explore Florida's best reef aboard the Sandie Cat, Key West’s newest and fastest catamaran. Spend less time traveling and more time in the crystal-clear waters. Enjoy a complimentary breakfast, unlimited mimosas (mango, strawberry, and orange), and draft beer during this all-inclusive experience. Join the crew for a true Key West experience with family and friends. Reserve your spot today!
Read moreBooked 5 times in last 48 hrs
57
Dip and Sip Afternoon Snorkel with Open Bar
55 ratings
3 Hrs.
Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie Cat is Key West's newest snorkeling catamaran, which allows you to get to the reef with speed, comfort, and some serious style. Join the captain and crew, round up your group, and hit the waves for an unforgettable Key West experience packed with fun, sun, and tasty spirits. This all-inclusive trip boasts an open well bar including unlimited mimosas (mango, strawberry & orange) & a variety of soft drinks! Book your spot today!
Read more
79
Sunset Sip and Sail with Open Bar and Live Music
53 ratings
2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!
Read more
64 60
Coral Reef Snorkeling Catamaran Trip with Margaritas Included
10 ratings
3 Hrs.
Experience the best afternoon you'll find on the straits of the Florida Keys by snorkeling this gorgeous coral reef. Climb aboard a luxurious catamaran as you cruise the crystal water to North America's only living coral reef. Dive into the sparkling, tropical water for underwater exploration, teeming with brightly colored tropical fish and corals. You don't have to be a jet setter to have a world-class time, so book your trip on this Coral Reef Snorkeling Catamaran Trip with Margaritas Included today!
Read more
73
Day Sail Aboard Schooner America 2.0
17 ratings
1.5 Hrs.
Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful water around Key West. Book your spot today!
Read more
117
Sunset Sail Aboard the Historic When and If
20 ratings
2 Hrs.
Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea. Book your Sunset Sail today!
Read more
144
Full Day Sail, Snorkel and Kayak Excursion
12 ratings
6.5 Hrs.
Get out on the water and experience nature at her finest with Full Day Sail, Snorkel, and Kayak Excursion complete with sailing, kayaking, and snorkeling. You'll see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the beauty around you. Live the island dream as you set sail on a 65-foot Schooner, then kayak through the mangrove forests. Snorkel the blue waters in search of tropical marine species. Book this Full Day Sail, Snorkel, and Kayak Excursion today and let your adventure begin!
Read more
100
Windjammer Champagne Sunset Sail
1 rating
2 Hrs.
Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West, Florida. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this cruise. Book today!
Read more