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Florida Keys Boating
Florida Keys boating is one the best ways to spend a day or two on vacation. 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 Florida Keys boating and sailing. 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 Florida Keys 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.
KEY LARGO
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.

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Heading Out for a Day of Florida Keys Boating |
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.
Quicksilver
- Location: Holiday Inn Docks
- Phone: (305) 451-0105
- Private charter and catamaran with bathroom onboard and fresh water shower to enjoy sailing the shore
ISLAMORADA
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.
MARATHON
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.
BIG PINE KEY
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.
Quick Links
Some sailing and boating facilities in Big Pine Key:
Jay Bird’s Powerboat Rentals
- Location: Big Pine Key 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.
KEY WEST
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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