Top Florida Sailing Trips

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 (4,791)
$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 (1,984)
$52.43
$51.43

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

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

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 (964)
$108.91
$107.91

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

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

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

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

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

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
Likely to Sell Out
Likely to Sell Out
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

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
Special Offer
Special Offer
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 (397)
$200
$199

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 (372)
$66.49
$65.49

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 (360)
$89
$88

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)
$66.67
$65.67

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

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

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

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