Florida Sailing Trips

104 Results
St. Augustine Live Music Sail with Drinks & Sunset Option

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, …More

St Augustine, USA

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised,...

1 hour 45 minutes Free Cancellation
4.8 (417)
from
$66
Fort Lauderdale Sailing Charter

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 …More

Fort Lauderdale, USA

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...

4 hours Free Cancellation
5.0 (401)
from
$95
Key West Sunset Sail Aboard Legendary Schooner Appledore

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 …More

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

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...

2 hours Free Cancellation
5.0 (368)
from
$99
4-Hour Fort Lauderdale Sailing Charter

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 …More

Fort Lauderdale, USA

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...

4 hours Free Cancellation
4.9 (323)
from
$110
Sunset Sail Cruise in Key West

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 …More

Key West, USA

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...

2 hours Free Cancellation
5.0 (292)
from
$102
Suncoast Sailing's Sunset Sailing Experience!

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. …More

St Petersburg, USA

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....

2 hours 30 minutes Free Cancellation
4.9 (285)
from
$70
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under …More

Likely to Sell Out
Likely to Sell Out
Clearwater, USA

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under...

2 hours Free Cancellation
5.0 (284)
from
$80
Classic Key West Schooner Sunset Sail with Full Open Bar

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 …More

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

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...

2 hours Free Cancellation
4.9 (282)
from
$109
Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. …More

Miami, USA

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google....

4 hours Free Cancellation
4.9 (259)
from
$150
Dolphin Adventure Sail in Cocoa Beach

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 …More

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

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...

2 hours Free Cancellation
4.9 (243)
from
$51
Sunset Sail in Miami: Complimentary Champagne Toast

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. …More

Likely to Sell Out
Likely to Sell Out
Miami, USA

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....

2 hours Free Cancellation
4.9 (231)
from
$129
Key West Schooner Backcountry Eco-Tour

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure! …More

Key West, USA

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...

5 hours (approx.) Free Cancellation
4.9 (216)
from
$110
Key West Day Sail on Schooner America 2.0 with 2 Drinks

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 …More

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

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...

1 hour 30 minutes Free Cancellation
5.0 (212)
from
$82
Sunset Catamaran Sail in Cocoa Beach

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 …More

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

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...

2 hours Free Cancellation
4.9 (206)
from
$56
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

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 …More

Naples, USA

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...

2 hours 30 minutes Free Cancellation
4.9 (196)
from
$70
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

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 …More

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

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...

2 hours Free Cancellation
4.9 (157)
from
$69
Private Sailing Tour through the Ten Thousands Islands

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 …More

Likely to Sell Out
Likely to Sell Out
Naples, USA

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...

2 hours
5.0 (154)
from
$450
Buccaneer Pirate Cruise in Destin

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger...

90 to 120 minutes Free Cancellation
4.8 (146)
from
$62
Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just …More

St Petersburg, USA

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just...

2 hours 30 minutes Free Cancellation
4.9 (118)
from
$65
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

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 …More

Key West, USA

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...

5 hours Free Cancellation
4.9 (118)
from
$119
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

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 …More

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

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...

2 hours Free Cancellation
5.0 (114)
from
$60

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