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Top 10 Best Florida Sailing Trips

Found 108 Sailing Trips activities in Florida. Sort by Popularity.
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.8 of 3,869 reviews)

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Free Cancellation
Start From $52.43
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • Florida
  • Superb3,869 reviews4.8

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....

    Free Cancellation
    Start From $52.43
 
 

Official Miami Millionaires Sightseeing Cruise

(4.3 of 906 reviews)

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Free Cancellation
Start From $18.00
 
Official Miami Millionaires Sightseeing Cruise Likely to Sell Out

Official Miami Millionaires Sightseeing Cruise

  • Florida
  • Exellent906 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,659 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $52.43
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • Florida
  • Superb1,659 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $52.43
 
 

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

(4.7 of 3,250 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres Likely to Sell Out

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

  • Florida
  • Superb3,250 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

(4.5 of 39 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 $599.99
 
50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party! Likely to Sell Out

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

  • Florida
  • Exellent39 reviews4.5

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 $599.99
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 666 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
Private Tour
Start From $99.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • Florida
  • Superb666 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 535 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Free Cancellation
Private Tour
Start From $52.95
 
Key West Snorkeling with Breakfast and Unlimited Mimosas Likely to Sell Out

Key West Snorkeling with Breakfast and Unlimited Mimosas

  • Florida
  • Exellent535 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Free Cancellation
    Private Tour
    Start From $52.95
 
 

St. Augustine Live Music Sunset Sail with Drinks Included

(4.7 of 186 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Private Tour
Start From $69.17
 
St. Augustine Live Music Sunset Sail with Drinks Included Likely to Sell Out

St. Augustine Live Music Sunset Sail with Drinks Included

  • Florida
  • Superb186 reviews4.7

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Private Tour
    Start From $69.17
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.7 of 64 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Private Tour
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • Florida
  • Superb64 reviews4.7

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 654 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • Florida
  • Superb654 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 837 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Private Tour
Start From $79.00
 
Sunset Sail in Key West with Beverages Included Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • Florida
  • Superb837 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Sunset Sip and Sail Key West with Open Bar and Live Music

(4.6 of 270 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Private Tour
Start From $79.95
 
Sunset Sip and Sail Key West with Open Bar and Live Music Likely to Sell Out

Sunset Sip and Sail Key West with Open Bar and Live Music

  • Florida
  • Superb270 reviews4.6

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Private Tour
    Start From $79.95
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 644 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
Private Tour
Start From $45.00
 
Panama City Beach Sunset Catamaran Sail on The Privateer Likely to Sell Out

Panama City Beach Sunset Catamaran Sail on The Privateer

  • Florida
  • Superb644 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
    Private Tour
    Start From $45.00
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 409 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
Private Tour
Start From $45.00
 
Panama City Beach Sunset Sail on The Footloose Catamaran Likely to Sell Out

Panama City Beach Sunset Sail on The Footloose Catamaran

  • Florida
  • Superb409 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
    Private Tour
    Start From $45.00
 
 

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,247 reviews)

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More

Free Cancellation
Private Tour
Start From $133.89
 
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres Likely to Sell Out

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

  • Florida
  • Superb1,247 reviews4.9

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....

    Free Cancellation
    Private Tour
    Start From $133.89
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 369 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • Florida
  • Exellent369 reviews4.5

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 67 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Free Cancellation
Private Tour
Start From $55.00
 
Buccaneer Pirate Cruise in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • Florida
  • Superb67 reviews4.9

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 286 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

Free Cancellation
Private Tour
Start From $69.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • Florida
  • Exellent286 reviews4.4

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

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

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

(4.4 of 356 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
Private Tour
Start From $59.07
 
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
  • Exellent356 reviews4.4

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

    Free Cancellation
    Private Tour
    Start From $59.07
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.7 of 35 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

Special Offer
Free Cancellation
Private Tour
Start From $39.20
(Saving 20% ) $49.00
 
-20% 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
  • Superb35 reviews4.7

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $39.20
    (Saving 20% ) $49.00
 
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