Sailboat Charter in Key West

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With or without captain
0 - $1,300+
Boat length
0 - 60+ ft
Boat power
0 - 400+ hp
Construction year
2002 - 2023
50 Max MI
5 sailboats available

Sailboat - 10.06m — 1980 Glander - 33 (1980)

From $762 per day


Sailboat - 12.5m — Island Trader - 41 (1990)

From $1,140 per day


Sailboat - 14.02m — Atlantic - Clipper 46 (1996)

From $988 per day


Sailboat - 9.75m — Lazy jack schooner - 32 (1990)

From $1,140 per day


Sailboat - 12.19m — Sailboat - 40 (1990)

From $1,726 per day

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Where to sail in Key West

Explore a favorite for both locals and tourists on board your sailboat charter in Key West. Create your own private boat tour whether it’s to make a sunset cruise, discover the waters of Key West, or even set sail further to the rest of Florida Keys. These beautiful waters are perfect for your sail charter. Find your perfect boat and let’s set sail and watch the sunset!

How much is a sailboat charter in Key West?

In Key West, sailboat charters can vary in price depending on the characteristics of the boat, the year it was constructed, the services included, and more.

What is there to see in Key West, Florida?

Discover the USA’s Florida Coast on a sailboat rental in Key West. This is the perfect getaway for the people who want to see some beautiful beaches and snorkel among some of the most interesting coral reefs in the Atlantic Ocean.

If you are planning your day sailing, we suggest heading to Dry Tortugas National Park! From Key West, it takes around 2 hours to arrive. This 100-square mile park is made up of 7 small islands and open water! Don’t forget your snorkeling gear with picturesque blue waters, superlative coral reefs, and marine life that will blow your mind.

In Key West, sailboat rentals are a one-of-a-kind experience you won’t want to miss. Whether you want to enjoy sunset sails, beautiful beaches and coves, or sandbars that are hidden.

Rent a sailboat with a captain in Key West

You can choose whether to rent a sailboat with a captain or without. To enjoy a bareboat charter, you will need a valid boating license for the boat you choose to rent. However, you can also choose to enjoy a sailboat charter in Key West with a captain and crew so you don’t have to worry about anything!

Charter a sailboat near Key West

In Key West, private sailboat are available to charter. See other boats in the area

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