Florida Sailing Trips

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$98
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

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 …More

Miami, USA

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...

3 to 30 minutes Free Cancellation
4.9 (12)
from
$600
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on...

2 hours Free Cancellation
5.0 (2)
from
$349
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything...

3 hours Free Cancellation
5.0 (2)
from
$599
Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of …More

Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of...

2 hours Free Cancellation
5.0 (2)
from
$338
6-Hour Sailing Charter from Fort Lauderdale

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 …More

Fort Lauderdale, USA

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...

6 hours Free Cancellation
5.0 (3)
from
$750
Private Catamaran: Snorkel, Swim and Dolphin Watching

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take...

3 hours Free Cancellation
5.0 (1)
from
$465
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

Key West, USA

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$127
Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and …More

Panama City Beach, USA

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and...

2 hours Free Cancellation
5.0 (3)
from
$760
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation
5.0 (3)
from
$124
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to …More

St Augustine, USA

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to...

2 hours Free Cancellation
4.8 (8)
from
$199
Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

Key West, USA

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation
5.0 (4)
from
$995
Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. …More

Key West, USA

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....

8 hours Free Cancellation
4.7 (19)
from
$107
Private Catamaran Sunset Cruise with Dolphin watching

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain …More

Destin, USA

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain...

2 hours Free Cancellation
5.0 (4)
from
$360
Nights of Lights Sailboat Tour St Augustine Sailing

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours …More

St Augustine, USA

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours...

2 hours Free Cancellation
5.0 (4)
from
$774
Private Sailing Charters on La Vie Dansante

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht …More

Daytona Beach, USA

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht...

3 hours Free Cancellation
5.0 (2)
from
$800
Private Boat Charter to Johns Pass Shell Key and Egmont Key

Cruise the beautiful waters of the Tampa Bay area on a private boat charter customized to your group. Explore popular destinations such as Shell Key, …More

St Petersburg, USA

Cruise the beautiful waters of the Tampa Bay area on a private boat charter customized to your group. Explore popular destinations such as Shell Key,...

4 hours Free Cancellation
5.0 (4)
from
$695
Private Sunset Sail in Key West Florida

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch …More

Key West, USA

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hours Free Cancellation
5.0 (1)
from
$750
All Inclusive Half Day Sunset Catamaran Adventure

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

6 hours Free Cancellation
5.0 (1)
from
$2,000
Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of …More

Panama City Beach, USA

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of...

1 hour 30 minutes Free Cancellation
from
$857
All Inclusive Full Day and Sunset Private Catamaran in St. Pete

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

8 hours Free Cancellation
from
$2,200

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