The Best Spots to Explore By Trailer Boat in South Florida
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  • Post last modified:October 7, 2020

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Your Boat Can Open a Wonderland in South Florida

One of the best things about owning a boat on a trailer is that you are not limited to your own neighborhood. With a suitable tow vehicle and a plan, you can experience all sorts of boating.

If you want a tropical getaway without the expense of traveling overseas, South Florida has pretty much everything you could ask for. From the vibrant nightlife and eclectic culture of Miami to the laid-back lifestyle of the Florida Keys, South Florida is the perfect place for exploring by trailer boat.

If your boat is big enough to overnight on, you’ll have more options. It’s pretty easy to plan a trip that divides your time between staying on anchoring and staying in hotels. But there are plenty of marinas and facilities in every area, so any type of boat can find just the right place to explore.

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Biscayne BayExplore Biscayne Bay by Boat

Miami sits on the northern edge of Biscayne Bay. Most of the bay is a national park and is therefore undeveloped. The bay is wide and open, with a few shallow spots that make for great flats fishing. Dolphins are a common sight here, and if you venture offshore of the outer islands, you will be in the uppermost reaches of the Florida Reef Track that stretches from here, southwest along the Florida Keys to the Dry Tortugas.

The official visitors center for Biscayne National Park is in Homestead, just south of Miami. From there, you can travel by boat the seven or so miles to Elliot Key on the eastern edge of the bay. Here you can see what the Florida Keys were originally like, a wilderness not unlike what you’ll find in the Everglades. The marina here caters to boat camping and can be busy during holiday weekends. There is also a popular day dock with picnic and beach facilities at Boca Chita Key. It’s hard to believe that such a remote place is so close to Miami.

By boat, it’s roughly sixteen miles north to Coconut Grove, one of the most underrated spots to explore Miami. You can continue up the Intracoastal Waterway to Miami Beach, Miami Bayfront Marina and Park, or even up to Fort Lauderdale. Heading south on the Intracoastal Waterway from Miami will put you in the Upper Keys and the bayside of Key Largo.

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Florida’s Everglades and Ten Thousand IslandsVisit Everglades National Park by Boat

The Everglades is one of the largest tracks of true wilderness east of the Mississippi River. Once covering all of South Florida, the Everglades is now limited to the very southwestern tip. Everglades National Park, Big Cypress National Preserve, and Ten Thousand Islands National Wildlife Refuge all make fantastic places to explore by boat.

The main hubs for boating activity, with ramps and facilities, from south to north are Flamingo, Chokoloskee, Everglades City, Goodland, and Marco Island. With miles and miles of mangrove coastline and unspoiled Gulf-side beaches, boating here is unlike anything you’ve likely done. Make sure your navigation skills are up to snuff and watch the water depth!

For the truly adventurous, check out the Wilderness Waterway, a 99-mile long winding trek through the mangroves and creeks connecting Everglades City and Flamingo. The route is popular in the winter months as a 7-day adventure trek for kayakers and canoers, but small vessels of all shapes can take the journey. Overhead tree canopies and shallow waters are the most limiting factors. Along the trail, you will find three kinds of backcountry campsites, including beaches, ground camping on the higher and dryer spots, and chickees. Chickees are elevated platforms built over the water where you can pitch your tent and sleep with the dolphins under the stars.

Note that boating in Everglades National Park requires completion of a free online course from the park service to help familiarize you with the unique aspects of navigation in the backcountry. Trips into the Everglades should be planned for winter months when bugs, especially mosquitoes and no-see-ums, are at a minimum.

Boating in The Florida Keys

The Florida Keys are decidedly very different depending on where you want to go. Key West, at the end of the road, is connected to the mainland via the 100-plus mile long Highway US 1. The Upper Keys are known for their small-town vibe and laid-back style. The Lower Keys share the same vibe until you get to Key West, which is the party town at the end of the road. Both areas have lots of boat ramps and facilities for trailerable boats.

One of the world’s largest barrier reefs lies offshore of the Florida Keys, making it one of the only places in the United States where you can see tropical corals and reef fish. It lies between five and seven miles offshore, so you’ll want to plan a trip on a calm day. The entire area lies within the Florida Keys National Marine Sanctuary. Summer months make lovely swimming and snorkeling here, and the wind is usually calm and the water warm.

To explore the Upper Keys, Key Largo and Islamorada are your best bests. Both have ramps and many marinas. Notably, John Pennekamp Coral Reef State Park in Key Largo has a beautiful facility with easy access to the oceanside reefs. The Upper Keys are known for world-class snorkeling and diving on the oceanside, and tranquil mangrove-lined coves on the bayside. The oceanside of the Keys is offshore territory, a shallow area of the open Atlantic. The bayside is protected waters, made up of Florida Bay and other smaller bays and coves. The kayaking, paddle boarding, and fishing are spectacular.

Farther south, the town of Marathon marks the beginning of the Lower Keys. From here, the bayside waters open up to the Gulf of Mexico, and the islands themselves become larger. Don’t miss Bahia Honda State Park, with its excellent boat ramp and small marina, which is a convenient spot to camp on your boat or head out to Looe Key National Marine Sanctuary. Looe Key is not an island at all, but one of the Lower Key’s largest coral reefs.

If you’re in the Florida Keys, you’ve got to go diving. Read my article on how to plan the perfect dive trip.

Charlotte Harbor and BoatingTrailer Yor Boat

This vast area lies on the southwestern edge of Florida and connects the cities of Punta Gorda, Fort Myers, Fort Myers Beach, Sanibel Island, and Captiva Island. There are quite a few quiet spots that you can only get to by boat as well. The entire area is protected by the outer barrier islands, meaning that pretty much any type of boat can explore here with the right weather.

The town of Boca Grande isn’t easy to get to by car, which makes it a unique spot to explore by boat. Boca Grande Pass is world-famous for its tarpon fishing. Just south, you’ll find the completely wild Cayo Costa State Park, accessible only by boat. Rent a cabin on the beach or camp on your boat in the protected cove near the marina. The island has miles of hiking and biking trails and is truly a special place.

Sanibel and Captiva Islands are popular island-getaway spots. The shelling here is excellent. As you head south, the next stop is Fort Myers Beach, which is a lively beach town with major resorts, fine dining, beachside seafood restaurants, and any other vice your heart desires. When you’re done exploring the outer islands, downtown Fort Myers lies twenty-odd miles up the Caloosahatchee River. You’ll find several marinas and hotels in the area. The downtown area is lined with shops and wonderful restaurants, making it a top-notch destination for boaters.

If you want to continue your adventure, the Caloosahatchee marks the beginning of the Okeechobee Waterway. A series of locks will take you through to Lake Okeechobee and then onto Stuart on the east coast. Charlotte Harbor has a lot to offer everyone


South Florida has some of the best boating destinations in the country. Florida is popular with tourists and visitors from all over the world, but only a select few get to experience it as boaters do. The state is bursting with scenic cruises and eco-tours, but nothing beats the experience of exploring these waters in your own boat on your own time.

John Allen

With more than a decade of experience cruising the lakes in my Crestliner Grand Cayman pontoon boat and my Boston Whaler, I now want to share everything I've learned with my community here at Boating Hub.

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