Top Florida Sailing Trips

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

Key West Signature Sunset Sail with Live Music, Open Bar & Food
Likely to Sell Out
Likely to Sell Out
Key West, USA

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (398)
$72
$71

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 (4,797)
$52.43
$51.43

Key West Dolphin and Snorkel Experience
Likely to Sell Out
Likely to Sell Out
Key West, USA

The Top10Adventures® Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.7 (331)
$69.95
$68.95

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Likely to Sell Out
Likely to Sell Out
Key West, USA

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (1,701)
$122.59
$121.59

Sunset Catamaran Cruise in Ft. Lauderdale
Special Offer
Special Offer
Fort Lauderdale, USA

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (696)
$129
$128

Key West Reef Snorkel & Sail Adventure
Likely to Sell Out
Likely to Sell Out
Key West, USA

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.8 (538)
$79
$78

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 (1,984)
$52.43
$51.43

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 (736)
$45
$44

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 (650)
$49.95
$48.95

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
Likely to Sell Out
Likely to Sell Out
Clearwater, USA

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (272)
$80
$79

Sunset Sail in Key West with Beverages Included
Likely to Sell Out
Likely to Sell Out
Key West, USA

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (960)
$79
$78

Southwest Florida Sunset Sail
Special Offer
Special Offer
Fort Myers, USA

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (502)
$70
$69

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

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 (212)
$50.85
$49.85

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
Likely to Sell Out
Likely to Sell Out
St Petersburg, USA

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.8 (324)
$77.97
$76.97

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Likely to Sell Out
Likely to Sell Out
Key West, USA

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours
2 hours
2 hours
4.9 (965)
$108.91
$107.91

Suncoast Sailing's Sunset Sailing Experience!
Special Offer
Special Offer
St Petersburg, USA

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

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.9 (279)
$69.99
$68.99

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 (188)
$56.49
$55.49

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

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