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Top 10 Best Florida Sailing Trips

Found 118 Sailing Trips activities in Florida. Sort by Popularity. - Page 2
 

Sunset Dolphin Sail Aboard the Privateer Catamaran

(4.8 of 747 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

Sunset Dolphin Sail Aboard the Privateer Catamaran

  • Florida
  • Superb747 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
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 249 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
  • Superb249 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
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 267 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

Classic Key West Schooner Sunset Sail with Full Open Bar

  • Florida
  • Superb267 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 Reef Snorkel & Sail Adventure

(4.7 of 568 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

Key West Reef Snorkel & Sail Adventure

  • Florida
  • Superb568 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: Sunset Sail + Reef Snorkel & Sandbar

(5 of 55 reviews)

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More

Free Cancellation
Start From $143.05
 
Key West: Sunset Sail + Reef Snorkel & Sandbar

Key West: Sunset Sail + Reef Snorkel & Sandbar

  • Florida
  • Superb55 reviews5

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....

    Free Cancellation
    Start From $143.05
 
 

Sunset Dolphin Sail Aboard the Footloose Catamaran

(4.8 of 482 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 $45.00
 
Sunset Dolphin Sail Aboard the Footloose Catamaran

Sunset Dolphin Sail Aboard the Footloose Catamaran

  • Florida
  • Superb482 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
 
 

Beach Island Shelling Cruise to Keewaydin Island Tour

(4.9 of 105 reviews)

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River in Naples Bay and head out to Keewaydin Island, a 7-mile barrier island, wit... More

Free Cancellation
Start From $56.00
 
Beach Island Shelling Cruise to Keewaydin Island Tour

Beach Island Shelling Cruise to Keewaydin Island Tour

  • Florida
  • Superb105 reviews4.9

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommoda....

    Free Cancellation
    Start From $56.00
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 468 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
  • Superb468 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
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 278 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. *Partic... 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
  • Superb278 reviews4.9

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

    Free Cancellation
    Start From $80.00
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 231 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More

Free Cancellation
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • Florida
  • Superb231 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....

    Free Cancellation
    Start From $50.85
 
 

Miami Private Yacht Celebration Cruise with Captain

(4.6 of 65 reviews)

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More

Free Cancellation
Private Tour
Start From $799.00
 
Miami Private Yacht Celebration Cruise with Captain Likely to Sell Out

Miami Private Yacht Celebration Cruise with Captain

  • Florida
  • Superb65 reviews4.6

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....

    Free Cancellation
    Private Tour
    Start From $799.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 323 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 $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • Florida
  • Superb323 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 $148.00
 
 

Southwest Florida Sunset Sail

(4.9 of 513 reviews)

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 sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Private Tour
Start From $70.00
 
Southwest Florida Sunset Sail Likely to Sell Out

Southwest Florida Sunset Sail

  • Florida
  • Superb513 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.5 of 74 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
  • Exellent74 reviews4.5

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 Dolphin Sunset Cruise (Adults only)

(4.9 of 148 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 Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • Florida
  • Superb148 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
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 282 reviews)

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. Just wind in the sails, salt in the air, and the kind of quiet glide ... More

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

Suncoast Sailing's Sunset Sailing Experience!

  • Florida
  • Superb282 reviews4.9

Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually suppos....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Sunset Sail Cruise in Key West

(4.9 of 295 reviews)

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 most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • Florida
  • Superb295 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 363 reviews)

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 passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore Likely to Sell Out

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • Florida
  • Superb363 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 1,003 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Private Tour
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses Likely to Sell Out

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • Florida
  • Superb1,003 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Fort Lauderdale Sailing Charter

(5 of 404 reviews)

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 beautiful blend of natural mangroves, luxurious waterfront homes, and ... More

Free Cancellation
Private Tour
Start From $150.00
 
Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • Florida
  • Superb404 reviews5

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....

    Free Cancellation
    Private Tour
    Start From $150.00
 
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