Sailing boat rentals in Florida Keys

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Type of boat charter
With or without a captain
Price per day
0 - $1,350+
Length of boat
0 - 196+ ft
Engine power
0 - 400+ hp
Year of manufacture
2003 - 2024
50 Max MI
2 sailboats available
No boats in Keystone, United States, see other boats nearby
These are our available boats around Keystone, United States

Beneteau - 373 | 6 people (11.37m)

St. Petersburg
With captain

From $779 per day

Custom - Merrit Walter | 20 people (16.76m)

Treasure Island
With or without a captain

From $1,495 per day

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All About Sailboat Rentals in the Florida Keys

Venture on the sailing trip of a lifetime as you explore exotic waters with your friends and family or special someone. Whether you have your own sailing license or not, it really doesn’t matter, as sailing with a skipper is an option we give our clients at Nautal. Sail with a skipper and relax as they show you the best parts of the Keys and give you inside info you would have never discovered by yourself! Alternatively, if you are a pro sailor, sail to Dry Tortuga National Park and visit these 7 utopian islands full of raw nature, wildlife and exotic sea life. 
A sailboat rental in the Florida Keys is perfect for exploring the 126 miles of exotic islands there is in the area. Other than relaxing onboard your sailboat rental in the Florida Keys, there are many other ways to enjoy the beautiful waters such as fishing, snorkelling or scuba diving … just to name a few. Why not become one with nature and observe the sea life and coral reef below? The Florida Keys is not only a beauty on the water but the islands also have a lot of fun to offer!
Distinguished from the rest of Florida because of its spectacular panoramic maritime views, luscious mangroves and easy-going — yet vibrant — atmosphere, the Florida Keys make for some of the best sailing in the world. With a large number of small islets and a captivating marine life to observe, you can sail with your rental sailboat on a unique adventure on the island by jumping from Key to Key. The overwhelming philosophy throughout the Florida Keys is "one human family" - expressing something of the love for nature and fellow travellers in this, one of the most exciting areas of the United States.

Ports and Areas of the Florida Keys

Within the Florida Keys’ main archipelago, you'll find easy-to-access marinas and ports offering vibrant nightlife and spectacular seafood overlooking glistening shores. When sailing from Key West, you can look to Islamorada, visiting the world-class Anne's Beach for glorious sun-soaked shores. Little Palm Island and Marathon Key are also must-sees, as areas famed for their dolphin populations and research stations. Next, Fero Blanco, Hawks Cay and Duck Key offer fine opportunities to fish (and cook), with Key Largo, finally, as the best area to anchor your sailboat rental and explore the nearby coral reef system.
Key West Harbour
Conch Key
Sailing in the Florida Keys
The Florida Keys is sandwiched between the Caribbean, Cuba and the Gulf of Mexico. As such, the area offers plenty of breathtaking sailing opportunities for you and your friends or loved ones to indulge in. Starting in Key West (easily accessible via plane) you can begin a circumnavigation of this alluring archipelago, or simply head out for more remote shores like the westernmost Key, Dry Tortugas. Chartering a sailboat for a week with a skipper is an ideal way to explore this melting pot of Floribbean culture. From coral reef ecosystems to abundant sea life and whale watching expeditions, sailing in the Florida Keys is an experience to behold.

Attractions in the Florida Keys

The Florida Keys are not simply a hotbed for utopian islands and clear blue waters. Ernest Hemingway lived in Key West from 1931 to 1939 and his beautiful house is now a museum that you can visit to learn all about his interesting and historically impressive life. 
After your informative time at the museum, why not go for a drink at Hemingway’s local, Sloppy Joe’s? Now called Captain Tony’s Saloon, this bar is located on Greene Street. 
You can also stop to observe the Southernmost Point Buoy at the very bottom of the US. This point was established in 1983 in Key West.

The climate in the Florida Keys

The Florida Keys not only gift sailors with beautiful views, scenery and nature, but also a sublime climate around most of the seasonal clock. 
We do not recommend renting a sailboat around July to November, as this season tends to be rainer and windier and depending on the area, can be known as “hurricane season”.

How to Get to the Florida Keys

Fly directly to the Keys from US locations such as Chicago, Miami, Orlando and New York. 
If you’re travelling other areas of Florida, you can also consider flying to Miami International Airport (MIA), which has plenty of international long-haul flights, and make your way down south. 

Charter a sailboat near Keystone

Privately owned sailboat are available for charter in Keystone. See other boats located in the area.

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