Florida Island Hopping: the Gulf ICW

Fort Myers Beach, Florida

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Fort Myers Beach, is a barrier island on the Gulf of Mexico that lies just south of the junction that marks the western end of the Okeechobee Waterway and the beginning of the Gulf Intracoastal Waterway. Fort Myers Beach has a rich history dating back 2,000 years to the Calusa Indians.

The best spot to dock on Fort Myers Beach is the Pink Shell Resort & Marina (855-482-1947, pinkshell.com). Experience their newly built floating docks adjacent to Bowditch Point on the north end of the island.

Begin your tour of the island with a bit of time travel at the Mound House (239-765-0865, moundhouse.org). Walk inside a Calusa Indian shell mound and discover the indigenous culture that Ponce de Leon met as he searched for the Fountain of Youth. Tour the William Case House which was built atop of the shell mound and has been restored to its 1921 grandeur.

A peaceful trail walk through an unspoiled mangrove canopy and oak hammock along the Back Bay awaits you at the Matanzas Pass Preserve (239-765-6794). Observe the flora and fauna native to Southwest Florida at this unique park which includes the Estero Island Historic Cottages.

Since the 1950s, Fort Myers Beach has been home to a large fleet of shrimp trawlers that harvest pink gold from the Gulf of Mexico. Dinghy over to San Carlos Island to visit the shrimp boats. Take a self-guided walking tour of working shrimp fleet and don't forget to buy some fresh pink shrimp right at the shrimp docks.

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Day 1- Sanibel and Captiva, Florida

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If you enjoy shelling, then the beaches of Sanibel Island offer the best location to pursue that hobby in Southwest Florida. If you are new to shelling you will soon learn the Sanibel stoop. As you walk along the beach bending down in hope of finding that rare junonia shell. And if you just want to learn more about shells, visit The Bailey-Matthew Shell Museum on Sanibel (3075 Sanibel Captiva Rd, 888-679-6450).

The only marina on Sanibel is appropriately named Sanibel Marina (239-472-2723, sanibelmarina.com) and is just about a mile away from the Sanibel Lighthouse and across San Carlos Bay from Fort Myers Beach. The marina is also home to Gramma Dot's Seaside Saloon, a local's choice for lunch or dinner (239-472-8138).About 10 miles north on the Gulf Intracoastal Waterway is the island of Captiva. According to local folklore got its name because the pirate Jose Gaspar kept his female captives there for ransom. Dock your boat at the Yacht Harbor at South Seas Island Resort (888-777-3625, southseas.com) and you can enjoy the amenities of one of the Top 10 Beach Resorts for Families. End your day watching a fabulous sunset over the Gulf of Mexico from the resort's beach.

A visit to Captiva is not complete without dinner at The Bubble Room (15001 Captiva Dr., 239-472-5558). Words cannot describe the eclectic nature of this restaurant, seeing is truly believing. From the uniforms of the servers to the restaurant's décor chock full of memorabilia, it is always a night to remember. And do save room for dessert!

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Day 2- Cabbage Key, Useppa Island and Cayo Costa

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Cruising about 15 miles further north on Gulf Intracoastal Waterway are three unique islands clustered together, each with their own ambiance.

‍Useppa Island (239-283-1061, useppa.com) is a private island club with Old Florida charm. In the early 1900s it was the center of tarpon sportfishing in Southwest Florida and was owned by wealthy Florida land owner and entrepreneur Barron Collier. The guests at his private retreat included Hollywood stars, tycoons and political bigwigs. Call ahead for dock space at the marina, lunch at the elegant Collier Inn and a tour of the island. You may want to join the club!If your tastes are a bit more laid back, dock at Cabbage Key (239-283-2278, cabbagekey.com) for lunch or dinner. Have a cheeseburger, and discover why it is rumored that after eating here, Jimmy Buffet was inspired to write his song Cheeseburger in Paradise. And if you get bored, try to count the dollar bills plastered all over the bar and restaurant by patrons throughout the years.

‍Cayo Costa is both a Florida State Park (941-964-0375) that is accessible only by water, and a barrier island with nine miles of pristine beaches and primitive campsites. Anchor for the night at Pelican Bay. If you enter from the north at Pelican Pass you will find deep water and a snug harbor for the night.

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Day 3- Boca Grande

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Just five miles to the north across Charlotte Harbor is Gasparilla Island with the town of Boca Grande as its heart. Boca Grande looks like a quaint Midwestern town dropped down onto a sandy island, which gives it a uniqueness. Katherine Hebpurn made Boca Grande her winter home and for the former Presidents Bush and their families it is a favorite Christmas holiday destination. The south end of Gasparilla Island at Boca Grande Pass is nexus of professional tarpon fishing tournaments. You may want to try your hand at catch and release with one of the many local fishing charter captains.

You can tie up at Whidden's Marina (941-964-2878, whiddensmarina.com) or Boca Grande Marina (941-964-2100, bocagrandemarina.net) depending on the draft and LOA of your yacht.

While dinner at the Main Dining Room of the Gasparilla Inn is a must, you can also enjoy lunch at Inn's Pink Elephant Restaurant (500 Palm Ave., 877-403-0599). And at the end of the day take a stroll along Lighthouse Beach to search for a fossil shark's tooth, which is a lucky find for beachcombers, and who knows it just may be your lucky day!