Top Florida Sailing Trips

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Special Offer
Special Offer
Key West, USA

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.9 (110)
$119
$118

Sunset Cruise Tour
Special Offer
Special Offer
Naples, USA

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (56)
$48.50
$47.50

Nights of Lights Sailboat Tour at St Augustine Sailing
Special Offer
Special Offer
St Augustine, USA

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours...

1 hour 15 minutesFree Cancellation
1 hour 15 minutesFree Cancellation
1 hour 15 minutes • Free Cancellation
5.0 (18)
$129
$128

Classic Key West Schooner Sunset Sail with Full Open Bar
Likely to Sell Out
Likely to Sell Out
Key West, USA

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (249)
$109
$108

Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise
Likely to Sell Out
Likely to Sell Out
Miami, USA

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google....

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.9 (259)
$150
$149

Bimini or Grand Bahama Island Day Cruise
Special Offer
Special Offer
Fort Lauderdale, USA

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear...

12 hoursFree Cancellation
12 hoursFree Cancellation
12 hours • Free Cancellation
3.9 (15)
$199
$198

Private Sailing Tour through the Ten Thousands Islands
Likely to Sell Out
Likely to Sell Out
Naples, USA

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s...

2 hours
2 hours
2 hours
5.0 (154)
$450
$449

Private Guided Sunset and Eco Tour up to 6 Passengers
Likely to Sell Out
Likely to Sell Out
Destin, USA

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (77)
$249.99
$248.99

Private Sailing on the Miami Bay - Biscayne Bay
Likely to Sell Out
Likely to Sell Out
Miami, USA

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Top10Adventures® Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate...

4 to 12 hoursFree Cancellation
4 to 12 hoursFree Cancellation
4 to 12 hours • Free Cancellation
5.0 (67)
$425
$424

2.5 hr Sailboat Tour aboard Orion's Child
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Top10Adventures® Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (91)
$130
$129

Key West Dolphin Watch and Sunset Sail on Catamaran
Likely to Sell Out
Likely to Sell Out
Key West, USA

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (40)
$117.17
$116.17

Key West Sail and Snorkel Day Trip from Fort Lauderdale
Special Offer
Special Offer
Fort Lauderdale, USA

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from...

15 hoursFree Cancellation
15 hoursFree Cancellation
15 hours • Free Cancellation
3.4 (14)
$149
$148

Fun Boat Rental with Captain in Miami Beach - up to 6 people
Special Offer
Special Offer
Miami, USA

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (52)
$260
$259

Schooner Appledore Day Sail with Full Bar in Key West
Likely to Sell Out
Likely to Sell Out
Key West, USA

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (113)
$49
$48

Private Charter: Shell Island Snorkeling & Dolphin Adventure
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.8 (31)
$1,900
$1,899

Private Swim, Snorkel & Sail on the Daydreams Sailboat
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (32)
$899
$898

Tiki Pub Glow Party Cruise (Adults only)
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (18)
$79.95
$78.95

Beach Island Shelling Cruise to Keewaydin Island Tour
Special Offer
Special Offer
Naples, USA

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (62)
$56
$55

Private Key West Sandbar and Paddle by Boat
Special Offer
Special Offer
Key West, USA

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
5.0 (37)
$600
$599

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami
Special Offer
Special Offer
Miami, USA

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (19)
$899
$898

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