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Top 10 Best Florida Sailing Trips

Found 108 Sailing Trips activities in Florida. Sort by Popularity. - Page 3
 

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 61 reviews)

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 party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Start From $59.00
 
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

  • Florida
  • Superb61 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $59.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 451 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • Florida
  • Superb451 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Start From $108.91
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 149 reviews)

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 enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • Florida
  • Superb149 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Start From $109.00
 
 

Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco

(5 of 158 reviews)

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More

Free Cancellation
Start From $143.05
 
Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco Likely to Sell Out

Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco

  • Florida
  • Superb158 reviews5

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....

    Free Cancellation
    Start From $143.05
 
 

Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks

(4.8 of 266 reviews)

Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of friends, bachelorette parties, and anyone looking to celebrate in style. Cruise the sparkling waters of Miami while enjoying your ... More

Free Cancellation
Private Tour
Start From $375.00
 
Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks Likely to Sell Out

Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks

  • Florida
  • Superb266 reviews4.8

Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of f....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Sunset Sail Aboard the 47 ft Daydreams Sailboat

(4.9 of 17 reviews)

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. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail Aboard the 47 ft Daydreams Sailboat Likely to Sell Out

Sunset Sail Aboard the 47 ft Daydreams Sailboat

  • Florida
  • Superb17 reviews4.9

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 293 reviews)

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 the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Private Tour
Start From $165.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • Florida
  • Superb293 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Bimini or Grand Bahama Island by Ferry

(3.4 of 11 reviews)

Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More

Free Cancellation
Private Tour
Start From $225.00
 
Bimini or Grand Bahama Island by Ferry Likely to Sell Out

Bimini or Grand Bahama Island by Ferry

  • Florida
  • Good11 reviews3.4

Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 32 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat Likely to Sell Out

Private Key West Sandbar and Paddle by Boat

  • Florida
  • Superb32 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Unforgettable Private Yacht Tour, Music, Drinks & Celebration Fun

(4.6 of 65 reviews)

Are you ready for an adventure? Join us for an unforgettable journey on our luxurious yacht, perfect for those who crave excitement and a deep connection with nature. Explore Miami's marine wonders aboard with all the comforts you... More

Free Cancellation
Private Tour
Start From $599.99
 
Unforgettable Private Yacht Tour, Music, Drinks & Celebration Fun Likely to Sell Out

Unforgettable Private Yacht Tour, Music, Drinks & Celebration Fun

  • Florida
  • Superb65 reviews4.6

Are you ready for an adventure? Join us for an unforgettable journey on our luxurious yacht, perfect....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.7 of 46 reviews)

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More

Free Cancellation
Private Tour
Start From $34.95
 
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach Likely to Sell Out

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

  • Florida
  • Superb46 reviews4.7

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....

    Free Cancellation
    Private Tour
    Start From $34.95
 
 

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

(4.9 of 70 reviews)

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 party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

  • Florida
  • Superb70 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Premium Miami Yacht Tour Experience: Captain, Champagne & Party!

(5 of 4 reviews)

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never before! Perfect for any special occasion, this VIP experience promises unforgettable memories Adventure Highlights Biscayne Bay ... More

Free Cancellation
Private Tour
Start From $50.00
 
Premium Miami Yacht Tour Experience: Captain, Champagne & Party! Likely to Sell Out

Premium Miami Yacht Tour Experience: Captain, Champagne & Party!

  • Florida
  • Superb4 reviews5

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

2-Hour Sunset Sailing With Wine In Stock Island

(5 of 81 reviews)

Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indulge in a variety of IPA, Import or domestic beers. Taste an assortment of appetizers. Enjoy a beautiful sunset while on the water.... More

Free Cancellation
Private Tour
Start From $133.89
 
2-Hour Sunset Sailing With Wine In Stock Island Likely to Sell Out

2-Hour Sunset Sailing With Wine In Stock Island

  • Florida
  • Superb81 reviews5

Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indu....

    Free Cancellation
    Private Tour
    Start From $133.89
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 17 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • Florida
  • Superb17 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.6 of 11 reviews)

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 and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $99.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise Likely to Sell Out

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • Florida
  • Superb11 reviews4.6

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise

(1 of 1 review)

Relax on a comfortable, shaded 2-hour Intracoastal Waterway Sightseeing Cruise aboard Motunui, a 50-ft open breeze catamaran with cushioned seating, tables, and deck-level restrooms. Enjoy a fully narrated tour showcasing Palm Bea... More

Free Cancellation
Private Tour
Start From $56.71
 
New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise Likely to Sell Out

New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise

  • Florida

Relax on a comfortable, shaded 2-hour Intracoastal Waterway Sightseeing Cruise aboard Motunui, a 50-....

    Free Cancellation
    Private Tour
    Start From $56.71
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 67 reviews)

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 day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Private Tour
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak Likely to Sell Out

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • Florida
  • Superb67 reviews4.9

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach

(4.9 of 209 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More

Free Cancellation
Private Tour
Start From $85.00
 
Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach Likely to Sell Out

Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach

  • Florida
  • Superb209 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

6-Hour Sailing Charter from Fort Lauderdale

(5 of 3 reviews)

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 the option to use their time docked or sailing out to sea. Once on the water... More

Free Cancellation
Private Tour
Start From $400.00
 
6-Hour Sailing Charter from Fort Lauderdale Likely to Sell Out

6-Hour Sailing Charter from Fort Lauderdale

  • Florida
  • Superb3 reviews5

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $400.00
 
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