Sailing in Florida

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The best out of 10 deals in Florida - enter dates to check availability

Top Sailing in Florida

Showing top 10 charters
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Listing image
Meet the Captain
Sailing silhouette

40 ft

up to 6

A Day on the Water

 
Fort Lauderdale
4 Hour – Sailing Adventure
You will cruise on the New River through downtown Ft Lauderdale to the Atlantic Ocean where we will set sail.We can take a maxium of 6 passengers.Sightseeing,ocean sailing and swimming.We have refrigeration on board so you can bring food and beverage.A clean bathroom on board as well.Your group will have a greaaaat fun and safe day on the water.
Price for up to 6 people
US $400
Listing image
Meet the Captain
Sailing silhouette

39 ft

up to 6

Sailingdaffy Inc

 
Fort Lauderdale
4 Hour Cruise – Half Day
Sailingdaffy Inc invites you to experience Fort Lauderdale’s sparkling waters aboard the 2008 Catalina 387 Sailing yacht. This well-maintained vessel comfortably accommodates up to six guests, ensuring an intimate and personalized adventure. Powered
Price for up to 6 people
US $500
Listing image
Sailing silhouette

41 ft

up to 12

Dolphin Landings Charter Boats – Phoenix

5.0
/5
(2 reviews)
 
St. Pete Beach
2 Hour – Private Sailing Charter
Set sail on a private 2-hour adventure aboard the 41ft yacht Phoenix, perfect for groups of up to 12 guests. Choose your preferred time of day—9:30 AM, 12:00 PM, or 2:30 PM—for a relaxing sail and the chance to spot dolphins. For a magical sunset sail, we typically depart about an hour before sunset. Message us for the exact departure time based on the date of your trip!
Instant Confirmation
Price for up to 12 people
US $908
Listing image
Sailing silhouette

46 ft

up to 12

Dolphin Landings Charter Boat – Fantasea

 
St. Pete Beach
2 Hour – Fantasea Private Sailing
Enjoy this beautiful 46' sailing yacht for your private charter for up to 12 guests! Great for any occasion when you want to wow your guests with something different and fun. We take pride in our excellent customer service, and this accommodating yacht brings beverages and finger food, or we can suggest local food and beverage options to top off your outing. Don't forget this vessel is child-friendly!
Instant Confirmation
Price for up to 12 people
US $1,008
Listing image
Sailing silhouette

51 ft

up to 14

Dolphin Landings Charter Sailing Yacht –Magic

5.0
/5
(1 review)
 
St. Pete Beach
2 Hr – Private Sailing Yacht Magic
Unwind and set sail on this 51ft yacht for 2 hours of pure enjoyment! Perfect for hosting family and friends for any occasion. Our captain and crew are dedicated to providing an exceptional experience!
Instant Confirmation
Price for up to 14 people
US $1,232
Listing image
Sailing silhouette

42 ft

up to 12

Treasure Coast Sailing Adventures

 
Stuart
2 Hour – Morning Discovery Sail
Sail at 10:30 and have the river mostly to yourself! Bring up to 12 passengers for two hours of sailing. Bring your own food and beverage, or we can provide it from one of the many restaurants nearby.
Price for up to 12 people
US $730
Listing image
Sailing silhouette

52 ft

up to 6

S.V. Sacred Space

 
Miami
8 Hour – Full Day Of Sailing
Cruise up the Intracoastal Waterway, passing through four drawbridges and the bustling Port Everglades, home to impressive freight and cruise ship terminals. Then head out through the Fort Lauderdale Inlet and into the open ocean for an unforgettable experience on the water.
Instant Confirmation
Price for up to 6 people
US $1,400
Listing image
Sailing silhouette

55 ft

up to 25

Sail the Suncoast Horizon!

5.0
/5
(2 reviews)
 
Treasure Island
2 1/2 Hour – Private Day Sailing
Set sail and explore all of the natural beauty the area has to offer! With the sails up, we can slip away and get up close and personal with the wild Atlantic bottlenose dolphins in Boca Ciega Bay or the Gulf of Mexico. Complimentary bottled water available. BYOB allowed. Cooler with ice available and a restroom aboard. Most trips venture out into the Gulf of Mexico, weather and conditions permitting. What's Included: Bottled Water Coolers with Ice Available Restroom Aboard What to Bring Sunscreen BYOB
Price for up to 25 people
US $1,745
Listing image
Sailing silhouette

45 ft

up to 6

Teal Tide Sailing – "Cay Michele"

 
St. Petersburg
3 Hour – Sunset Sail
Private captained sail through the protected waters of Boca Ciega Bay, with a beautiful view of the sun on an open Gulf Horizon! You're welcome to bring any of your own food or drinks to accompany you on the evening sail!
Instant Confirmation
Price for up to 6 people
US $900
Listing image
Sailing silhouette

36 ft

up to 6

Wine Down Sailing

 
Pensacola
2 Hour – Sunset Sail
Come aboard for a private sunset sailing experience. The boat is all yours for you and your crew - no sharing the boat with strangers.
Price for up to 6 people
US $495
Listing image
Meet the Captain
Sailing silhouette

40 ft

up to 6

A Day on the Water

 
Fort Lauderdale
4 Hour – Sailing Adventure
You will cruise on the New River through downtown Ft Lauderdale to the Atlantic Ocean where we will set sail.We can take a maxium of 6 passengers.Sightseeing,ocean sailing and swimming.We have refrigeration on board so you can bring food and beverage.A clean bathroom on board as well.Your group will have a greaaaat fun and safe day on the water.
Price for up to 6 people
US $400
Listing image
Meet the Captain
Sailing silhouette

39 ft

up to 6

Sailingdaffy Inc

 
Fort Lauderdale
4 Hour Cruise – Half Day
Sailingdaffy Inc invites you to experience Fort Lauderdale’s sparkling waters aboard the 2008 Catalina 387 Sailing yacht. This well-maintained vessel comfortably accommodates up to six guests, ensuring an intimate and personalized adventure. Powered
Price for up to 6 people
US $500
Listing image
Sailing silhouette

41 ft

up to 12

Dolphin Landings Charter Boats – Phoenix

5.0
/5
(2 reviews)
 
St. Pete Beach
2 Hour – Private Sailing Charter
Set sail on a private 2-hour adventure aboard the 41ft yacht Phoenix, perfect for groups of up to 12 guests. Choose your preferred time of day—9:30 AM, 12:00 PM, or 2:30 PM—for a relaxing sail and the chance to spot dolphins. For a magical sunset sail, we typically depart about an hour before sunset. Message us for the exact departure time based on the date of your trip!
Instant Confirmation
Price for up to 12 people
US $908
Listing image
Sailing silhouette

46 ft

up to 12

Dolphin Landings Charter Boat – Fantasea

 
St. Pete Beach
2 Hour – Fantasea Private Sailing
Enjoy this beautiful 46' sailing yacht for your private charter for up to 12 guests! Great for any occasion when you want to wow your guests with something different and fun. We take pride in our excellent customer service, and this accommodating yacht brings beverages and finger food, or we can suggest local food and beverage options to top off your outing. Don't forget this vessel is child-friendly!
Instant Confirmation
Price for up to 12 people
US $1,008
Listing image
Sailing silhouette

51 ft

up to 14

Dolphin Landings Charter Sailing Yacht –Magic

5.0
/5
(1 review)
 
St. Pete Beach
2 Hr – Private Sailing Yacht Magic
Unwind and set sail on this 51ft yacht for 2 hours of pure enjoyment! Perfect for hosting family and friends for any occasion. Our captain and crew are dedicated to providing an exceptional experience!
Instant Confirmation
Price for up to 14 people
US $1,232
Listing image
Sailing silhouette

42 ft

up to 12

Treasure Coast Sailing Adventures

 
Stuart
2 Hour – Morning Discovery Sail
Sail at 10:30 and have the river mostly to yourself! Bring up to 12 passengers for two hours of sailing. Bring your own food and beverage, or we can provide it from one of the many restaurants nearby.
Price for up to 12 people
US $730
Listing image
Sailing silhouette

52 ft

up to 6

S.V. Sacred Space

 
Miami
8 Hour – Full Day Of Sailing
Cruise up the Intracoastal Waterway, passing through four drawbridges and the bustling Port Everglades, home to impressive freight and cruise ship terminals. Then head out through the Fort Lauderdale Inlet and into the open ocean for an unforgettable experience on the water.
Instant Confirmation
Price for up to 6 people
US $1,400
Listing image
Sailing silhouette

55 ft

up to 25

Sail the Suncoast Horizon!

5.0
/5
(2 reviews)
 
Treasure Island
2 1/2 Hour – Private Day Sailing
Set sail and explore all of the natural beauty the area has to offer! With the sails up, we can slip away and get up close and personal with the wild Atlantic bottlenose dolphins in Boca Ciega Bay or the Gulf of Mexico. Complimentary bottled water available. BYOB allowed. Cooler with ice available and a restroom aboard. Most trips venture out into the Gulf of Mexico, weather and conditions permitting. What's Included: Bottled Water Coolers with Ice Available Restroom Aboard What to Bring Sunscreen BYOB
Price for up to 25 people
US $1,745
Listing image
Sailing silhouette

45 ft

up to 6

Teal Tide Sailing – "Cay Michele"

 
St. Petersburg
3 Hour – Sunset Sail
Private captained sail through the protected waters of Boca Ciega Bay, with a beautiful view of the sun on an open Gulf Horizon! You're welcome to bring any of your own food or drinks to accompany you on the evening sail!
Instant Confirmation
Price for up to 6 people
US $900
Listing image
Sailing silhouette

36 ft

up to 6

Wine Down Sailing

 
Pensacola
2 Hour – Sunset Sail
Come aboard for a private sunset sailing experience. The boat is all yours for you and your crew - no sharing the boat with strangers.
Price for up to 6 people
US $495

Top Sailing Destinations

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Other great boat types in Florida

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