Florida Keys Sailing Boating

Sailing & Boating

Blue skies and crystal clear waters with different color intensity are just two of the main features brought to our mind when it comes to sailing and boating in the Florida Keys.

Everything here is reminiscent to the Caribbean: flora, fauna, water, weather, and even the festive mood of those Islands, but with the convenience of sailing in the United States, where you have the Coast Guard and all the facilities and amenities just around the corner.

From sand deserts surrounded by mangroves to marinas, there are plenty of opportunities for sailing and boating throughout Key Largo, Islamorada, Marathon, Big Pine Key, and Key West.

In each and every one of the Florida Keys you will find sailing facilities, classes, and more, as well as equipped sailboats and powerboats rentals, besides information, maps and expert guidance of professional captains and sailor men.

Miami, Florida City, and Forth Lauderdale, in the nearby mainland, are other options to hire sailing services, boats, and powerboats. Keeping the draft of charter boats below 4 feet will allow you to sail through all the Florida Keys.

Remember, sailing and boating provide you with other recreational opportunities, such as diving, snorkeling, fishing or just relaxing aboard under the sun of the Floridian paradise.


Located in the Upper Keys, Key Largo is the unpolluted region of the Florida Keys, where some caution is advised to navigate around the coral reefs. Growing coral and seagrass beds blend with the color of water, making it unable to determine how deep the bottom is, whether you are close or away from the shore.

If your are sailing in Key Largo for the very first time, it is advised to have the guidance of professional that can teach you how to “read” the water color for safe navigation and what to do in emergency case.

Some sailing and boating facilities in Key Largo:

Morning Star Charters

Location: Key Largo Fisheries

Phone: (305) 451-7057

Boat charters, including a 50′ sailing yacht, with multiple opportunities for relaxing, snorkeling, diving, or having fun.


Location: Holiday Inn Docks

Phone: (305) 451-0105

Private charter and catamaran with bathroom onboard and fresh water shower to enjoy sailing the shore


There is no better place to find sailing and boating enthusiasts that are just right, the so-called “Sportfishing Capital of the World” and it really is!

You will find plenty of boating facilities for every type of boating activity. Islamorada is also the right spot for windsurfing, fishing charters and enjoying freshly caught seafood.

Some sailing and boating facilities in Islamorada:

Coconut Cove Resort & Marina

Location: 84801 Old Highway

Phone: (305) 664-0123

Accommodations, restaurants and all the sailing facilities that you would expect from a world-class marina can be found in this place.

Bud n’ Mary’s Fishing Marina

Location: MM 79.8 – Oceanside

Phone: (305) 664-2461

Another marina providing accommodations, boat tours, party fishing boats, boat rentals and other sailing facilities.

Seacamp Association Inc.

Location: 1300 Big Pine Avenue

Phone: (305) 872-2331

A cooperative non-profit effort dedicated to educate youth in marine science. Providing boating and sailing information.


Sailing in Marathon is a pleasure encompassing all the surrounding Middle Keys, enjoying a breeze that brings to mind the lure of the Caribbean Sea without leaving the American coast.

There are many sailing clubs and sailing adventures to help you enjoy in the heart of the Florida Keys. However, powerboats are better for zipping out throughout the small islands, because some of the channels are narrow and swallow.

Some sailing and boating facilities in Marathon:

Adios Charters

Location: Marathon Marina

Phone: (305) 360-6826

A service providing fishing and boating services, plus some of the best equipment in the Keys.

Fish’n Fun Rentals

Location: Next to the Boat House Marina

Phone: (305) 743-2275

Waterfront boat rental and equipped boats with full day and weekly discounts for those who want to be their own captain.

Two Conchs Dive & Fishing Charters

Location: 10800 Overseas Highway

Phone: (305) 743-6253

Bay wrecks fishing and offshore fishing in aboard a 31 feet Contender and 300 horsepower Yamahas.


Sailing and boating in the lower Keys is to approach the third largest living reef in the world, one of the treasures of the Florida Keys declared the National Marine Sanctuary.

Snorkeling and diving within the protected area is allowed so you can sail straight to this place and enjoy the underwater life and ecosystem of this region, visited by more than one million people each year.

Some sailing and boating facilities in Big Pine Key:

Jay Bird’s Powerboat Rentals

Location: Big Pine Keyai Fishing Lodge

Phone: (305) 872-8500

Boat rentals, fishing charters, diving, snorkeling adventures offshore, and exploring the mangroves around this place,

Patriot Boat Rentals

Location: Boggie Road

Phone: 305-872-0409

All what you need to live an unforgettable experience boating and sailing through Big Pine Key and the Lower Keys.


Located on the tip of the Florida Keys, Key West is basically a tourist destination where you can enjoy sailing and boating with other attractions included.

However, you can still rent your own powerboat or even a yacht to explore the surrounding waters or approach Cuba without leaving the limits of the United States.

Some sailing and boating facilities in Key West:

Liberty Fleet of Tall Ships

Location: Hilton Resort and Marina

Phone: (305) 292-0332

Daily tours aboard one of two ships, the Liberty and the Liberty Clipper, including parasailing, sunset cruises, and special events

Yankee Freedom II

Location: Land’s End Marina

Phone: (305) 294-7009

Catamaran that takes you to Dry Tortugas in a 2-hours trip, leaving you at Fort Jefferson and returning to pick you up several hours later.

Discovery Glass Bottom Boat Tours

Location: 251 Margaret Street, Land’s End Marina

Phone: (305) 293-0099

Two-hour sailing trips aboard a glass bottom boat enjoying underwater views of coral and fish life on reefs surrounding Key West.

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