Top Florida Sailing Trips

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 (61)
$34.95
$33.95

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.9 (1,519)
$35
$34

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (4)
$40
$39

Sunset Dolphin Sail Aboard the Privateer 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 the SV Privateer,...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (738)
$45
$44

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 (465)
$45
$44

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

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

Key West Reef Morning Snorkeling with Breakfast and Mimosas
Special Offer
Special Offer
Key West, USA

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.7 (651)
$49.95
$48.95

Tiki Pub Amazing Dolphin Eco Adventure
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (7)
$49.95
$48.95

Dolphin Adventure Sail in Cocoa Beach
Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (214)
$50.85
$49.85

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
Special Offer
Special Offer
Panama City Beach, USA

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (4,802)
$52.43
$51.43

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
Special Offer
Special Offer
Panama City Beach, USA

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (1,988)
$52.43
$51.43

Buccaneer Pirate Cruise in Destin
Likely to Sell Out
Likely to Sell Out
Destin, USA

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (131)
$55
$54

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 (61)
$56
$55

Sunset Catamaran Sail in Cocoa Beach
Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (189)
$56.49
$55.49

Key West Afternoon Reef Snorkeling with Open Bar
Likely to Sell Out
Likely to Sell Out
Key West, USA

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.6 (436)
$59.95
$58.95

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

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

Afternoon Schooner Clearwater Beach Cruise Sailing
Likely to Sell Out
Likely to Sell Out
Clearwater, USA

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (2)
$65
$64

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 (374)
$66.49
$65.49

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