Top Florida Sailing Trips

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

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

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

Champagne Dolphin Sail and Reef Snorkel
Likely to Sell Out
Likely to Sell Out
Key West, USA

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...

3 hours
3 hours
3 hours
5.0 (9)
$108.91
$107.91

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 (246)
$109
$108

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Special Offer
Special Offer
Pensacola, USA

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (65)
$114
$113

Key West Wreckers Race Aboard Schooner America 2.0
Special Offer
Special Offer
Key West, USA

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
3 hours
3 hours
4.9 (14)
$116.10
$115.10

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 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

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (1)
$120
$119

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
Likely to Sell Out
Likely to Sell Out
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

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

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

Sunset Sail in Miami: Complimentary Champagne Toast
Likely to Sell Out
Likely to Sell Out
Miami, USA

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine....

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (231)
$129
$128

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

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: Sunset Sail + Reef Snorkel & Sandbar
Likely to Sell Out
Likely to Sell Out
Key West, USA

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? •...

4 hours 30 minutesFree Cancellation
4 hours 30 minutesFree Cancellation
4 hours 30 minutes • Free Cancellation
5.0 (40)
$143.05
$142.05

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

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

Frequently Asked Questions

These answers are based on answers previously given to Top10Adventures® customers' questions.

Florida Adventures
Attractions
Guides
Calendar
Language
Currency

Site Settings

Activity name

Currency

Activity name

Sorting, ranking, and search results

Activity name

Top10Adventures® wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Top10Adventures® over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.