Sailboat charter in Florida Keys

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

Sailboat - 12.2m — BENETEAU - 40 (2004)

From $1,368 per day


Sailboat - 4.57m — Beneteau - Idyllle 15.5 (1987)

From $1,064 per day


Sailboat - 14.6m — BENETEAU - 48' (2014)

From $1,026 per day


Sailboat - 9.14m — Hunter - Cherubini (1977)

From $882 per day


Sailboat - 14.33m — Beneteau - 461 (2000)

From $760 per day


Sailboat - 12.19m — Beneteau - Oceanis 40 (2000)

From $195 per day

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Where to sail with your sailboat charter in the Florida Keys

You can find sailboats to rent with or without a captain in the Florida Keys on the Ocean Evasion website. Use the filters to help you find the best sailboat charter in the Florida Keys that suits your needs whether it's in the United States or in the world. You can also choose to do a yacht charter, bareboat charter, and more! Explore the Keys and their history, beauty, and be at one with nature as you cruise the aqua waters.

The Florida Keys is made up of 5 islands: Key Largo, Islamorada, Marathon, Lower Keys, and Key West. These islands are the perfect mix of arts, culture, and natural beauty whether under the water or above. You have endless possibilities of places to explore during your sailboat rental in the Florida Keys, whether it's coral reefs, nature trails, or beaches.

How much is it to rent a sailboat in the Florida Keys?

Renting a sailboat in the Florida Keys can vary in price depending on the characteristics of the boat, the added services, and amenities. These added services and amenities can include the captain, meals that are included in the rental, and more.

What is there to see in the Florida Keys?

In your sailboat charter in the Florida Keys, there is so much to see! You can go through each of the 5 islands and visit all of the beautiful parts of the island. From Key Largo to Key West you have plenty of small islands, coves, and cays to explore.

You could choose to go from Key Largo to the southernmost point of the USA, Key West! Or start from Key West and head all the way to Miami or Fort Lauderdale. The choices are endless when you have a private boat rental and the freedom to go everywhere you want.

Here are some of our personal favorites to visit while on your sailboat charter in the Florida Keys:

  • Dry Tortugas National Park
  • Indian Key
  • Biscayne Bay

 Rent a sailboat with a captain in the Florida Keys

In the Florida Keys, sailboat rentals can be done with or without a captain. This is great news if you guys want to take charge of your ship and set sail without a captain. To charter a bareboat, you will need to check that you have a valid boating license for the boat you chose.

You can also choose to enjoy your sailboat charter in the Florida Keys with a captain. This is great if you are looking to sit back and relax while someone takes care of the technicalities of sailing. You can even ask your captain to give you some tips on sailing or even show you the basics while you're sailing away in the Florida Keys.

 What is the best time to go to the Florida Keys?

In the sunshine state, it is always a great time to go! From October to May the temperature is around 89-72°F. However, from August to October it is hurricane season so we suggest you keep an eye on the news during these months! From November to April the weather is a little cooler, however, it is still great for sailing! The temperature during these months ranges from 82°F to 65°F.

Charter a sailboat near Florida Keys

In Florida Keys, private sailboat are available to charter. See other boats in the area

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