America's Other Coast: Cruising the Gulf of Mexico

Find pristine natural beauty and charming local character in these four ports of call along the Gulf of Mexico.


I still remember the first time I cruised the Gulf of Mexico. My family chartered a CSY 33 that almost blew up when a hot water heater caught fire during the night. This brush with death, however, is not what made this trip a standout in my memory. It was the the cruising grounds we explored. I have since had the pleasure of returning on multiple occasions and, every time, I leave more enamored with the region than before.

But despite the serenity and the number of destinations that line the Gulf coast of Florida, it doesn't seem to garner the same amount of attention as the east coast. And maybe that's a good thing and a contributing factor to the region's charm. I've always felt you cruise through destinations on the east coast of Florida, but you go cruising on the west coast. In order to do so properly, keep in mind that if you have six feet on the depth sounder, that's considered deep. I've found bottom on more than one occasion while cruising from my former home port of Naples, Florida.

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The variety of the region allows the cruiser to enjoy a vast array of experiences and after a week or two, you'll feel like you've been gone much longer. Larger metropolitan areas such as Sarasota, Tampa, Naples, and Ft. Myers dot the landscape, filled in by hidden gems such as the Little Shark River and the barrier islands of Pine Island Sound.

If, like many boaters, you move your boat south for the winter, consider leaving your boat on this coast for a season. We're only touching upon a sliver of the area, but moving up the coast and into Florida's Panhandle is also another road less traveled that deserves attention -stay tuned for future issues. But when planning your initial Gulf of Mexico cruise, these are four must-stop destinations that will leave a lasting impression on you, too. Enjoy.

Useppa Island

****In the past, I have bypassed this exclusive island, believing that transients were frowned upon. However, today Useppa Island and the members-only resort does allow transient dockage. The marina has six feet of controlling depth and can accommodate vessels up to 110 feet. A Get Acquainted membership pass can be acquired and is worth the price of admission, especially if you are already a guest at the marina. The exclusive nature of the island has resulted in a pristine, unspoiled environment oozing with Old Florida charm.

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Cabbage Key

Located on the Pine Island Sound, northwest of Ft. Myers Beach, is the 100 acre island of Cabbage Key. When I first visited the island 25 years ago during the aforementioned charter, I thought we had discovered our own secret paradise. Well, I was wrong. The island is a popular destination for cruisers and day trippers alike. Walkers will relish the network of nature trails marked to identify various fauna. Plan to take in a refreshment afterwards at the Cabbage Key Bar, which has served thirsty boaters and sportsmen for more than 60 years. The bar is infamous for the dollar bills pasted on the walls by patrons. Make sure you leave yours.

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Cayo Costa

This tiny barrier island just north of Sanibel and to the west of Cabbage Key is a Florida State Park. The park rents out small cabins. I'm itching to stay in one of these for a week. You can walk across the island from the anchorage to the beach, which offers superb shelling and swimming.

Gasparilla Island

After a few days of exploring Cayo Costa and Cabbage Key, you may wish to ease back into civilization. Gasparilla is just the place to do it. The barrier island lies at the intersection of Boca Grande Pass and Charlotte Harbor. Controlled development has resulted in an area that is truly the best of both worlds. Put away the flip-flops and T-shirts for the night and head up to the Gasparilla Inn. This special spot has been hosting visitors since 1913. The Inn's Pink Elephant restaurant is open for lunch and dinner. The village of Boca Grande is known as "Florida's Nantucket" thanks to the quaint brick streets lined with boutiques, galleries and restaurants. Be sure to take the bike path that stretches from town out to the lighthouse.