Sailboat Rental in Florida

Add your dates
With or without a captain
Price per day
0 - $1,350+
Boat length
0 - 196+ ft
Engine power
0 - 400+ hp
Year of manufacture
2003 - 2024
Search radius
250 Max MI
34 sailboats available

Catalina 387 (2008)

Fort Lauderdale
With captain
 6  · Super owner

From $1,027 per day

Sailboat Sea Ray 54 17m (2000)

North Bay Village
With or without a captain

From $3,832 per day

Real sailing experience (1981)

With captain

From $633 per day

See the skyline of New York City (2003)

Pompano Beach
With captain

From $998 per day

Luxury Coastal Sailboat Cruises -- The Best of Southeast Florida!! (2000)

Pompano Beach
With captain

From $1,285 per day

Day Charter with Hunter Cherubini (1977)

With captain

From $919 per day

Private Charter on Beneteau 373 in St.Petersburg! (2007)

St. Petersburg
With captain

From $776 per day

Custom 52 feet Pirate Vessel (2010)

Key Largo
With captain

From $1,451 per day

Sailboat Custom Merrit Walter 16.76m

Treasure Island
With or without a captain

From $1,490 per day

Beneteau Oceanis 40CC (2000)

With captain

From $1,297 per day

Sailboat Galeon 50 16m (2017)

With or without a captain

From $3,991 per day

Beautiful Modern Sailing 40' Catamaran (2006)

With captain

From $1,584 per day

Jeanneau Sun Odyssey 349 (2019)

St. Augustine
With captain

From $1,548 per day

Beneteau 48 (2014)

With captain

From $1,069 per day

Hunter 36 Sailboat (2015)

With captain

From $1,267 per day

The Mistress - 37 ft. Gulfstar Sloop Sailboat (1978)

Palm Beach
With captain

From $3,220 per day

Sailboat Custom 19.12m

Key West
With or without a captain

From $2,258 per day

BENETEAU 461 - Coconut Grove (2000)

With captain

From $792 per day

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Sailboat Rental in Florida with Click&Boat

Rent a sailboat in Florida, the so-called 'sunshine state' on the south-eastern coast of the United States that attracts more than 100 million visitors every year. In Miami, a trendy and multicultural city that never sleeps, you can relax on the sandy beaches, or stroll around the vibrant streets of the city, lined with coconut trees, and admire the luxurious villas.

Or perhaps choose to set sail in the Florida Keys, from island to island. Key Largo to Key West is doable in one week! And for those looking for a very laid-back sailing trip, try exploring Florida’s western coast in charming destinations like Cape Coral and Tampa. No matter what destination you choose to set sail to in Florida, we are sure you will love it!

So what are you waiting for? Come sail in Florida!

How much does it cost to rent a sailboat in Florida?

The cost of a sailboat rental in Florida depends on a few factors. For example, prices may be influenced by the size and model of the boat, and if it is high or low tourism season in the area. Extras like fuel, water sports equipment, and the services of a captain may come at an additional cost. So to be sure, contact the boat owner via Click&Boat’s messaging platform to ask any questions you may have.

  • Sailboat rentals in Florida start at $275/day for 4 people.
  • For larger sailboat rentals accommodating more than 6 people, expect to pay $1,115/day.

Since you are interested in renting a sailboat in Florida, we also recommend you check out our fleet in nearby destinations:

Where to set sail in Florida:

Florida has endless sailing opportunities- whether you are interested in sailing the Atlantic Ocean to the Bahamas archipelago, or cruising the waters of the Gulf of Mexico, we are sure you’ll find the perfect destination in Florida for a sailboat rental! Here are some of our top sailing destinations:

Miami is a must! While it is a popular vacation spot, renting a sailboat puts a whole new twist to your vacation! You can visit downtown Miami for a few hours, then set sail for Miami Beach, Fort Lauderdale, or Palm Beach for the day. From the pristine beaches to fun sandbars and delicious restaurants for a dock’n’dine experience, you’ll never be bored in Miami!

You can’t miss the Florida Keys when you come to South Florida. Key West will offer you a one-of-a-kind sailing experience, from snorkeling and diving to visiting nearby keys like Islamorada and Marathon.

On Florida’s western boat, set sail from Cape Coral, Naples, or Tampa. These charming destinations offer great day trip opportunities to visit the hundreds of islands hidden in the gulf, like Captiva Island and Sanibel Island.

When is the best time to sail in Florida?

Florida is a sailor’s paradise most of the year! You can set sail from late Fall to late Spring, however, we suggest the late Spring as being the best time to sail due to fewer crowds. Generally, the late summer tends to be hurricane season.

If you are interested in a sailboat rental in Florida, we highly recommend that you make a reservation in advance with Click&Boat to ensure that you can set sail on board the perfect boat.

Are sailboat rentals available with a captain?

Yes! With Click&Boat, most sailboat rentals in Florida are available with an experienced captain and crew. All you have to do is sit back and relax while the skipper and crew take care of everything from navigating, docking, and more! This is also a great option for those who are planning parties or celebrations on board!

Our captains are local experts who know the area best! Allow them to show you their favorite places: from lovely seaside towns to sandy beaches, coves, and islands. They might even have recommendations on the area’s best restaurants and bars if you are interested in docking’n’dining.

For those interested in bareboat charters and who have the proper sailing qualifications, contact our owners on Click&Boat for more information and availabilities.

Why charter a sailboat for your next sailing adventure?

Sailboat rentals are ideal for anyone interested in learning to sail, wanting a unique day on the water, or for those who plan to sail for a longer period of time and require cabins.

Depending on the model and length of the sailboat, they can typically accommodate 4 to 6 guests comfortably. This is a great option for small families and couples.

Imagine yourself cruising along the Florida Keys, stopping to relax at a beach, and most importantly- creating unforgettable memories with your loved ones. Sailing charters are definitely a bucket-list-worthy adventure!

Renting a sailboat with the Click&Boat platform

With Click&Boat, the leading peer-to-peer boat rental service, guests can select from a range of sailboats like Beneteau, Catalina, Hunter, as well as other types of boats like deck boats and jet skis. And rest assured that we will help you find a boat that fits your budget and suits your needs.

Once you have found the perfect yacht charter, send a message to a boat owner using our internal messaging system in order to clarify any questions you may have. After that, all that is left to do is book your rental. And after your experience aboard, be sure to leave a review.

However, if you prefer, you can request a free quote from our team of knowledgeable sailing advisors. They will help you rent a boat, as well as help you plan all the details of your sailing trip in Florida.

Rent a sailboat near Florida

In Florida, privately owned sailboat are available for rent. See other boats in the area

Rent another type of boat in Florida

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