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
Nov 27 - Dec 3
Narrow your search
Private Trip
Public Trip
Swim Friendly
Cruise Only
Restroom
Captain Included
1-6 passenger
13-20 passenger
21-40 passenger
41-75 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)
Air Controlled Cabin
Food/Drink Available
Live Music
Kid Friendly (All Ages)
80
Key West: Southernmost Sunset Sail with Live Music & Hors d’oeuvres
4.7(211)
2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!
Read more
60
Key West: Catamaran Champagne Sunset Sail
4.9(101)
1.5 Hrs.
Set sail on a Catamaran Champagne Sunset Sail in Key West for an unforgettable evening. Sip complimentary drinks as the ocean breeze carries you into a breathtaking sunset, fading into a star-filled sky. Whether with family or someone special, relax, unwind, and savor the beauty of Key West. Book your Champagne Sunset Sail today!
Read more
52
Key West: Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas
4.5(39)
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 more
86 80
Key West: Sunset Cruise with Live Music & Cocktails Included
4.9(85)
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
Key West: Morning Reef Snorkel and Sail with Unlimited Mimosas
5.0(33)
3 Hrs.
Imagine yourself swimming in the warm tropical water of Key West, Florida with swarms of vibrant colorful fish all around you as you begin the day with a Morning Reef Snorkel and Sail with Unlimited Mimosas aboard an expansive 69’ sailing catamaran. 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
57
Key West: Dip and Sip Snorkeling Adventure with Open Bar Included
4.7(55)
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
91
Key West: Sunset Sip and Sail with Open Bar and Live Music
4.8(53)
2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back on a Sunset Sip and Sail with Open Bar and Live Music 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
Key West: Coral Reef Snorkeling Catamaran Trip with Margaritas Included
4.8(10)
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
125
Key West: Schooner Champagne Sunset Sail with Complimentary Beverages Included
5.0(11)
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!
Read more
80
Key West: Double Dip 2 Stop Snorkel Adventure
5.0(7)
3 Hrs.
Experience snorkeling in the Florida Keys on an adventure like no other. Explore the crystal-clear water on this two-stop double-dip snorkel trip. Travel aboard the fastest catamaran around to explore North America's last coral reef. Dive in and venture out amongst the abundant marine life in 2 different locations with top-of-the-line provided snorkeling gear. Get acquainted with some of the most magical marine creatures as you swim around in their natural habitats during this underwater tour. Enjoy complimentary beer and wine served after. Book your experience now!
Read more
135
Key West: Bugeye Schooner Backcountry Eco Tour Aboard the Appledore Star
5.0(1)
5 Hrs.
Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This Bugeye Backcountry Tour is an amazing mix of sailing, snorkeling, and kayaking among the most scenic settings in the Florida Keys, including the Sponge Garden Reef and Mangrove Island. Discover the amazingly diverse ecosystem of Key West’s backcountry and observe the abundant wildlife from the water. This tour is a MUST for outdoor enthusiasts! Book your spot today!
Read more
55
Key West: Windjammer Schooner Day Sail with Complimentary Beverages Included
Be the first to review!
2 Hrs.
Catch the wind on an historic, dual-masted sailing vessel for a pleasure cruise through beautiful Key West, Florida with a Windjammer Schooner Day Sail. Journey the calm, tropical waters to view landmark sites like Fort Zachary Taylor, the Navy Mole, and opulent Sunset Key. Sample a wide variety of premium complimentary drinks like homemade sangria, draft beer, premium wine, and more. Climb aboard an authentic sailing schooner for this luxurious day sail and cast your cares into the warm breeze. Book your spot today on this Windjammer Schooner Day Sail.
Read more