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Top 10 Best Florida Sailing Trips

Found 130 Sailing Trips activities in Florida. Sort by Popularity. - Page 2
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.8 of 189 reviews)

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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure

  • Florida
  • Superb189 reviews4.8

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 94 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 $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • Florida
  • Superb94 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 $59.95
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 167 reviews)

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More

Free Cancellation
Start From $79.50
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • Florida
  • Superb167 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Start From $79.50
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 543 reviews)

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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • Florida
  • Superb543 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 338 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Special Offer
Free Cancellation
Start From $62.95
(Saving 10% ) $69.95
 
-10% Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • Florida
  • Exellent338 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Special Offer
    Free Cancellation
    Start From $62.95
    (Saving 10% ) $69.95
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 447 reviews)

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 for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • Florida
  • Superb447 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Start From $129.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 373 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Start From $59.95
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • Florida
  • Exellent373 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Start From $59.95
 
 

Sunset Sail in Miami: Complimentary Champagne Toast

(4.8 of 234 reviews)

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. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More

Free Cancellation
Start From $129.00
 
Sunset Sail in Miami: Complimentary Champagne Toast Likely to Sell Out

Sunset Sail in Miami: Complimentary Champagne Toast

  • Florida
  • Superb234 reviews4.8

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....

    Free Cancellation
    Start From $129.00
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 261 reviews)

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Free Cancellation
Start From $69.99
 
Suncoast Sailing's Sunset Sailing Experience! Likely to Sell Out

Suncoast Sailing's Sunset Sailing Experience!

  • Florida
  • Superb261 reviews4.9

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....

    Free Cancellation
    Start From $69.99
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 222 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
  • Superb222 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
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 95 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
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
  • Superb95 reviews4.9

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

    Free Cancellation
    Start From $119.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 693 reviews)

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 as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Start From $129.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • Florida
  • Superb693 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Start From $129.00
 
 

Sunset Dolphin Sail Aboard the Privateer Catamaran

(4.8 of 711 reviews)

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, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Free Cancellation
Start From $45.00
 
Sunset Dolphin Sail Aboard the Privateer Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Privateer Catamaran

  • Florida
  • Superb711 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Start From $45.00
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 32 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
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
  • Superb32 reviews5

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

    Free Cancellation
    Start From $89.00
 
 

Sunset Dolphin Sail Aboard the Footloose Catamaran

(4.8 of 444 reviews)

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 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Start From $40.00
 
Sunset Dolphin Sail Aboard the Footloose Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Footloose Catamaran

  • Florida
  • Superb444 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Start From $40.00
 
 

Key West Champagne Sunset Catamaran Cruise

(4.7 of 587 reviews)

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More

Free Cancellation
Start From $59.00
 
Key West Champagne Sunset Catamaran Cruise Likely to Sell Out

Key West Champagne Sunset Catamaran Cruise

  • Florida
  • Superb587 reviews4.7

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....

    Free Cancellation
    Start From $59.00
 
 

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

(4.7 of 309 reviews)

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 dolphin or two! This is the only charter offering service from downtown St. Petersb... More

Free Cancellation
Start From $66.67
 
4-Hour St. Pete Pier to Egmont Key Experience by Ferry Likely to Sell Out

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

  • Florida
  • Superb309 reviews4.7

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....

    Free Cancellation
    Start From $66.67
 
 

Bimini or Grand Bahama Island by Ferry

(3.4 of 17 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
Start From $225.00
 
Bimini or Grand Bahama Island by Ferry Likely to Sell Out

Bimini or Grand Bahama Island by Ferry

  • Florida
  • Good17 reviews3.4

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

    Free Cancellation
    Start From $225.00
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.5 of 86 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast Likely to Sell Out

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • Florida
  • Exellent86 reviews4.5

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Start From $49.00
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 230 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
Start From $80.00
 
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach Likely to Sell Out

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

  • Florida
  • Superb230 reviews4.9

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

    Free Cancellation
    Start From $80.00
 
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