Sailboat Charter in Key West

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With or without a captain
0 - $1,300+
Boat length
0 - 196+ ft
Boat power
0 - 400+ hp
Construction year
2003 - 2024
50 Max MI
Guests usually rent sailboats and catamarans from Saturday to Saturday. To receive the best options, adjust your search dates.
7 sailboats available

Sailboat - 19.12m — Custom

Key West
With or without a captain

From $2,244 per day

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

Key West
With captain

From $1,181 per day

Sailing yacht - 32m — Schrooner - 105 (2011)

Key West
With captain

From $6,058 per day

Sailboat - 12.19m — Sailboat - 40 (1990)

Key West
With captain

From $1,786 per day

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

Key West
With captain

From $771 per day

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

Key West
With captain

From $1,181 per day

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

Sailboat - 13.78m — Jeanneau - Sun Odyssey (2001)

With captain

From $881 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. Sailing charters range from $709 per day to up to $1,999 for private charters.

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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