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Top 10 Best Florida Sailing Trips

Found 130 Sailing Trips activities in Florida. Sort by Popularity. - Page 3
 

Sail & Splash Excursion in Ft. Lauderdale

(4.8 of 270 reviews)

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 one of the best cruise Ft Lauderdale has to offer . Sit back... More

Free Cancellation
Start From $129.00
 
Sail & Splash Excursion in Ft. Lauderdale Likely to Sell Out

Sail & Splash Excursion in Ft. Lauderdale

  • Florida
  • Superb270 reviews4.8

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....

    Free Cancellation
    Start From $129.00
 
 

Private Boat - Snorkeling, Star Island & Dolphin Spotting

(4.5 of 61 reviews)

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More

Free Cancellation
Private Tour
Start From $65.00
 
Private Boat - Snorkeling, Star Island & Dolphin Spotting Likely to Sell Out

Private Boat - Snorkeling, Star Island & Dolphin Spotting

  • Florida
  • Exellent61 reviews4.5

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 314 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
  • Superb314 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
 
 

Sunset Dolphin Sail Aboard the Daydreams Sailboat

(4.9 of 32 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 Dolphin Sail Aboard the Daydreams Sailboat Likely to Sell Out

Sunset Dolphin Sail Aboard the Daydreams Sailboat

  • Florida
  • Superb32 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
 
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 10 reviews)

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Free Cancellation
Private Tour
Start From $950.00
 
Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • Florida
  • Superb10 reviews5

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

(4.9 of 12 reviews)

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More

Free Cancellation
Private Tour
Start From $500.00
 
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay Likely to Sell Out

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

  • Florida
  • Superb12 reviews4.9

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 

Key West Day Sail on Schooner America 2.0 with 2 Drinks

(4.9 of 199 reviews)

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More

Free Cancellation
Private Tour
Start From $79.45
 
Key West Day Sail on Schooner America 2.0 with 2 Drinks Likely to Sell Out

Key West Day Sail on Schooner America 2.0 with 2 Drinks

  • Florida
  • Superb199 reviews4.9

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a ....

    Free Cancellation
    Private Tour
    Start From $79.45
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 147 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Special Offer
Free Cancellation
Private Tour
Start From $59.45
(Saving 15% ) $69.95
 
-15% Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • Florida
  • Superb147 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $59.45
    (Saving 15% ) $69.95
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 173 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
Private Tour
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • Florida
  • Superb173 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 37 reviews)

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 wind. This tour is perfect for all ages and offers a wide-open, unob... More

Free Cancellation
Private Tour
Start From $117.17
 
Key West Dolphin Watch and Sunset Sail on Catamaran Likely to Sell Out

Key West Dolphin Watch and Sunset Sail on Catamaran

  • Florida
  • Superb37 reviews4.7

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lig....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

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

(4.8 of 268 reviews)

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More

Free Cancellation
Private Tour
Start From $150.00
 
Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks Likely to Sell Out

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

  • Florida
  • Superb268 reviews4.8

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 106 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Day Sailing Experience! Likely to Sell Out

Suncoast Sailing's Day Sailing Experience!

  • Florida
  • Superb106 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 152 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Free Cancellation
Private Tour
Start From $450.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • Florida
  • Superb152 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

St Augustine Nights of Lights Tour with Live Music and Sunset Opt

(4.7 of 69 reviews)

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the illuminated bayfront, the Bridge of Lions, and Castillo de... More

Free Cancellation
Private Tour
Start From $69.17
 
St Augustine Nights of Lights Tour with Live Music and Sunset Opt Likely to Sell Out

St Augustine Nights of Lights Tour with Live Music and Sunset Opt

  • Florida
  • Superb69 reviews4.7

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday ....

    Free Cancellation
    Private Tour
    Start From $69.17
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 177 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Florida... More

Free Cancellation
Private Tour
Start From $56.49
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • Florida
  • Superb177 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $56.49
 
 

Fun Boat Rental with Captain in Miami Beach - up to 6 people

(4.9 of 51 reviews)

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More

Free Cancellation
Private Tour
Start From $260.00
 
Fun Boat Rental with Captain in Miami Beach - up to 6 people Likely to Sell Out

Fun Boat Rental with Captain in Miami Beach - up to 6 people

  • Florida
  • Superb51 reviews4.9

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 36 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
  • Superb36 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
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 466 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
Private Tour
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
  • Superb466 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Fort Lauderdale Sailing Charter

(5 of 388 reviews)

You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as the “Venice of America." The New River offers a blend of natural beauty, luxurious homes, and fascinating history. Your adventure ... More

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

Fort Lauderdale Sailing Charter

  • Florida
  • Superb388 reviews5

You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as th....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Private Sailing on the Miami Bay - Biscayne Bay

(4.9 of 75 reviews)

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More

Free Cancellation
Private Tour
Start From $425.00
 
Private Sailing on the Miami Bay - Biscayne Bay Likely to Sell Out

Private Sailing on the Miami Bay - Biscayne Bay

  • Florida
  • Superb75 reviews4.9

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....

    Free Cancellation
    Private Tour
    Start From $425.00
 
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