Charter a sailing boat in Key West

Add your dates
With or without a skipper
Price per day
0 - €1,200+
Boat length
0 - 60+ m
Engine power
0 - 400+ hp
Year of manufacture
2003 - 2024
Search radius
100 Max Km
7 sailboats available

1980 Glander 33 (1980)

Key West
With skipper

From €700 per day

Sailboat Custom 19.12m

Key West
With or without a skipper

From €2,037 per day

Schrooner 105 (2011)

Key West
With skipper

From €5,500 per day

Lazy Jack Schooner 32 (1990)

Key West
With skipper

From €1,072 per day

Sailboat 40 (1990)

Key West
With skipper

From €1,622 per day

Island Trader 41 (1990)

Key West
With skipper

From €1,072 per day

See more nearby boats
These boats are available around Key West, United States

Day or Sunset Sailing on a 45.2 Jeanneau! (2001)

With skipper

From €800 per day

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A personal advisor will help you, click here

Sailboat Charter in Key West with Click&Boat

Founded in 1822, Key West is rich in history, culture, and entertainment. The best way to get to know this laid-back town is by boat. Enjoy a sailing experience in Key West during your next visit. Come aboard a sailboat and fall in love with the Florida Keys just like Ernest Hemingway did!

With a sailboat charter in Key West, you can visit the sandy beaches and bays of the area by day and head to the city's nightclubs and bars in Mallory Square by night. We recommend that you visit the nearby keys of Islamorada and Marathon.

How much does it cost to rent a sailboat in Key West?

The price of a sailboat hire in Key West, 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 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 charters in Key West start at 400€/day and may cost up to 1,845€ /day for larger and newer boats.
  • Schooners are available in Key West and prices start at 325for sunset cruises for up to 6 people.

Since you are interested in chartering a sailing boat in the Florida Keys, we also recommend you check out our fleet in nearby destinations:

Sailing in Key West

As the southernmost point of both Florida and the United States, Key West is a boating destination with sunshine, history, and character that makes it worth visiting year-round. This island city is known for its conch-decorated houses and bars and restaurants dotted along Duval Street. If you charter a sailboat in Key West you can explore the beautiful reefs nearby that have ideal conditions for snorkeling and diving.

Many who decide to book a sailboat charter in Key West, also sail to the rest of the Florida Keys, a collection of tropical islands spanning over 80 miles. Diving lovers in particular love this part of Florida for its shipwrecks and rich marine life, including colorful tropical fish, stingrays, and dolphins. So keep Islamorada, Marathon, Stock Island, and Key Largo in mind!

For those interested, you can set off on a boat tour of Dry Tortugas National Park, which includes 7 islands and is famous for its crystal-clear waters; it’s also home to lovely sea turtles!

If you are planning a longer stay in South Florida, consider a sailing trip from Key W

When is the best time to sail in the Florida Keys?

Florida is a paradise for sailors year-round. You can set sail from late Fall to late Spring, however, we suggest the late Spring as being the best time to visit and sail due to fewer crowds. Generally, the late summer tends to be hurricane season.

If you are interested in a sailboat hire in Key West or in any of the Florida Keys, 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.

Can I charter a sailboat with a skipper? 

Yes! With Click&Boat, most sailboat rentals in Key West 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 pick a sailboat for your next adventure?

Sailboat hires 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 discovering the FL Keys, stopping to watch the sunset, relaxing at a beach, and most importantly- creating unforgettable memories with your loved ones. Sailing charters are definitely a bucket-list-worthy adventure!

Chartering a sailing boat 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 catamarans and motorboats. 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 boat, send a message to an owner 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 charter a yacht, as well as help you plan all the details considering your boat rental in Key West.

Charter a sailboat near Key West

In Key West, privately owned sailboat are available for charter. See other yachts in the area

Charter another yacht type in Key West

Are you interested in other yachts besides Sailboat in Key West?
Look up at other yachts to charter on our website

Our client reviews
4.9 / 5
Score calculated based on 313416 reviews
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Aug 18, 2021
Fun place with beautiful waters and nice reefs for snorkeling or diving. Good food and bars onshore also.