Top Florida Sailing Trips

Sunset Dolphin Sail Aboard the Footloose Catamaran
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (466)
$45
$44

Key West Day Sail on Schooner America 2.0 with 2 Drinks
Likely to Sell Out
Likely to Sell Out
Key West, USA

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (210)
$79.45
$78.45

Suncoast Sailing's Day Sailing Experience!
Likely to Sell Out
Likely to Sell Out
St Petersburg, USA

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.9 (117)
$64.99
$63.99

Sail & Splash Excursion in Ft. Lauderdale
Special Offer
Special Offer
Fort Lauderdale, USA

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
4.9 (274)
$129
$128

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
Likely to Sell Out
Likely to Sell Out
Clearwater, USA

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (62)
$34.95
$33.95

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (111)
$59.95
$58.95

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (142)
$69
$68

Shallow Water Snorkeling and Dolphin Watching in Key West
Likely to Sell Out
Likely to Sell Out
Key West, USA

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4 hours
4 hours
4.8 (437)
$108.91
$107.91

Fort Lauderdale Sailing Charter
Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (398)
$150
$149

4-Hour Fort Lauderdale Sailing Charter
Special Offer
Special Offer
Fort Lauderdale, USA

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.9 (318)
$148
$147

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Special Offer
Special Offer
Naples, USA

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.9 (188)
$70
$69

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
Special Offer
Special Offer
Miami, USA

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
4.9 (450)
$129
$128

Private Sunset and Eco Tour in Destin-Up to 16 Guests
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 (45)
$450
$449

Sunset Sail Cruise in Key West
Likely to Sell Out
Likely to Sell Out
Key West, USA

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (285)
$95
$94

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (52)
$89
$88

St. Augustine Live Music Sail with Drinks & Sunset Option
Special Offer
Special Offer
St Augustine, USA

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised,...

1 hour 45 minutesFree Cancellation
1 hour 45 minutesFree Cancellation
1 hour 45 minutes • Free Cancellation
4.8 (376)
$66.49
$65.49

Sunset Dolphin Sail Aboard the Daydreams Sailboat
Special Offer
Special Offer
Panama City Beach, USA

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island....

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (37)
$99
$98

St Augustine Nights of Lights Tour with Live Music and Sunset Opt
Special Offer
Special Offer
St Augustine, USA

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the...

1 hour 45 minutesFree Cancellation
1 hour 45 minutesFree Cancellation
1 hour 45 minutes • Free Cancellation
4.7 (68)
$82.69
$81.69

Key West Sunset Sail Aboard Legendary Schooner Appledore
Special Offer
Special Offer
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 (361)
$89
$88

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 (109)
$119
$118

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