Top Florida Sailing Trips

Private Sunset Sail in Key West Florida
Special Offer
Special Offer
Key West, USA

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (1)
$750
$749

Private Catamaran: Snorkel, Swim and Dolphin Watching
Special Offer
Special Offer
Destin, USA

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (1)
$465
$464

6-Hour Sailing Charter from Fort Lauderdale
Special Offer
Special Offer
Fort Lauderdale, USA

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have...

6 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
5.0 (3)
$750
$749

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront
Special Offer
Special Offer
St Augustine, USA

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (8)
$199
$198

Ultimate Party in Miami : Boat Party, Party Bus & Nightclub
Special Offer
Special Offer
Miami, USA

This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious double-decker boat transformed into a moving nightclub with...

3 hours
3 hours
3 hours
4.0 (11)
$189
$188

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt
Special Offer
Special Offer
Destin, USA

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply...

3 hours
3 hours
3 hours
5.0 (1)
$75
$74

Private Afternoon Snorkel with Sunset Sail in Key West
Special Offer
Special Offer
Key West, USA

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (4)
$995
$994

Nights of Lights Sailboat Tour 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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (4)
$774
$773

Original Cruisin Tikis Snorkeling Safari
Special Offer
Special Offer
Destin, USA

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart...

3 hours
3 hours
3 hours
5.0 (1)
$69
$68

South Beach Miami BACHELORETTE Boat Day!
Special Offer
Special Offer
Miami, USA

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (1)
$1,795
$1,794

Private Sailing Charters on La Vie Dansante
Special Offer
Special Offer
Daytona Beach, USA

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (1)
$800
$799

All Inclusive St Pete Private Half Day Catamaran Charter
Special Offer
Special Offer
St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
$1,700
$1,699

All Inclusive Half Day Sunset Catamaran Adventure
Special Offer
Special Offer
St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

6 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
$2,000
$1,999

All Inclusive Full Day Luxury Catamaran Charter
Special Offer
Special Offer
St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

7 hoursFree Cancellation
7 hoursFree Cancellation
7 hours • Free Cancellation
$2,100
$2,099

All Inclusive Full Day and Sunset Private Catamaran in St. Pete
Special Offer
Special Offer
St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

8 hoursFree Cancellation
8 hoursFree Cancellation
8 hours • Free Cancellation
$2,200
$2,199

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