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Island Hopping

By Staff | Feb 17, 2016

Cabbage Key is one of the midpoint stops on a barrier island hopping journey, where a tremendous burger can be eaten at the historic Cabbage Key Restaurant. Photo by BRIAN WIERIMA/illustration by Michael Pistella

There’s an adventure starting anywhere off the coast of Southwest Florida which can bring stops with its own unique personality at each one.

Several different worlds can be visited all in one day trip on the water by either one’s personal watercraft or by charter supplied by Captiva Cruises, which are the experts of barrier island hopping through the Pine Island Sound.

There are numerous barrier islands which line the Gulf of Mexico on one side and the Pine Island Sound on the other. That unique set up alone makes these barrier islands one of the best and popular estuaries in the United States.

“The conditions are perfect here to attract an abundance of different wildlife,” said Captiva Cruise’s Paul McCarthy, who has 30 years of experience of guiding tours through Pine Island Sound and the barrier islands. “Estuaries are the best places to attract wildlife and fish, because it’s where salt water meets fresh water, which brings in them all.

“We happen to have one of the best estuaries in the U.S. because it’s where salt, fresh, clean and clear water meets.”

Although Useppa Island is an exclusive, private island, Captiva Cruises is contracted with the club to stop at the restaurant there. The marina at Useppa contains dolphins and a bevy of other marine wildlife. BRIAN WIERIMA

Pine Island Sound is one of the best bodies of water to enjoy boating, since it is protected on all sides of it. The barrier islands protect it from the Gulf of Mexico’s tides and winds, while one of Florida’s largest island – Pine Island – protects it from the North.

Its shallow waters are also a perfect breeding ground for wildlife, since sunlight is able to penetrate all the way to the bottom, making it a lush field for sea grasses. That in return, produces an abundance of photosynthesis, which produces lots of oxygen and breeds an abundance of life.

It’s also perfect habitat for manatees, dolphins, a variety of birds and fish.

Add in the beautiful barrier islands, which each brings its own personality, it’s the making of a paradisiacal journey.

“Each stop at a barrier island is a different world to experience,” McCarthy said.

The Captiva Cruise captains are experts of navigating through Pine Island Sound and its channels to safely transport guests to all the different barrier islands. BRIAN WIERIMA

But safety is the first item boaters must have in mind when they plan their island hopping day. Since the Sound is shallow, there are many sandbars which are hazards.

Marine markers are placed around the Sound, marking the best navigational route. Going in between the green and red markers is the safest way.

“There is a saying when boating and watching for the markers, and that’s ‘Red is right return,'” McCarthy said. “The red marker will be on your right side when you are leaving and on your left when you return.

“If you go in between the green and red markers, it’s going through the gate and the safest, because it’s the deepest water.”

It is not safe to use a straight line route, but always use the aid of the markers because of the depth of the water. Also know what tide it is, either low or high, this makes a two-feet difference in depth.

The best tool, though, to avoid sandbars and running aground is the boater’s vision, so keeping an eye out for shallow waters is a must.

Navigating through or across is a pass – which is the opening from the sound to the Gulf – is also riskier, since the winds and tides from the Gulf make it a much rougher ride.

“I recommend if you are cruising and island hopping, you start earlier in the morning and come back in the afternoon,” McCarthy said. “Then you’ll be able to get a full day in and have a chance to stop at all the different places, have lunch at one of them and explore more.”

North Captiva is one of the first stops which can be made first. Much of the island is uninhabited, especially in the middle portion. Anchoring near the island’s coast is recommended.

Shelling and birding are two popular activities. The unique aspect also is starting in an estuary on one side, walking about 200 yards over the island and coming to another whole biosphere, which of course, is the Gulf of Mexico and beautiful, undeveloped beaches.

The hop over to Cayo Costa State Park is a must stop. The island is only accessible by boat and is a conservation state park, with only a few dwellings on it, since the vast majority is owned by the State of Florida.

There, hiking or biking can be done, as a boat can dock in Pelican Bay, where the main marina is located. This destination is the untouched paradise of the barrier islands.

It has nine miles of pristine beaches to shell and see a variety of birds or tortoises. The setting is that of a Gilligan’s Island, truly a paradise to behold.

Boats can also anchor in Pelican Bay, which is protected by Cayo Costa and another barrier island, which provide calm waters and a potential overnight stay on a comfy cabin cruiser.

If the island hopper can peel themselves off of Cayo Costa, without setting up reservations to camp in one of the many camping spots on the island, it’s off to Cabbage Key and Useppa Islands.

Cabbage Key boasts one of the most famous island restaurants, serving Cheeseburger in Paradise, which was dubbed by Jimmy Buffett, supposedly when he was visiting the island.

The island is one of the higher elevated islands, which is due to the Calusa Indian shell mound. The restaurant there has a full menu, as the island hopper can relax, stretch out, have a cocktail and burger.

A cruise through Useppa Marina, which is an exclusive and private island – but accessible with Captiva Cruises – sports dolphins in the water and beautiful homes, including the clubhouse of which was Baron Collier’s original home.

The history of each of Cabbage Key and Useppa is rich and contains much of what old Florida was all about, including tarpon fishing, the most popular activity of its time.

The journey next stops at Boca Grande and Gasparilla Island. Boca Grande, which is on Gasparilla Island, was also a destination for the affluent, after the shipping harbor in Boca Grande Pass was closed, due to Tampa Bay taking over the industry.

Instead, the railroad company marketed the island to the rich and famous in the Northeast U.S. because they could transport the guests in railcars, from New York all the way to Boca Grande.

Today, the sites of the affluent still exists, with a trip through Boca Grande Marina boasts of multi-million dollar yachts.

After docking, Boca Grande gives the old Florida feel, with the quaint little town featuring many old-style restaurants and the Gasparilla Inn, where rich and famous still stay, including former U.S. President George and Barbra Bush.

Walking the boardwalks gives one the feel of living in the early 1900’s, with golf carts being the preferred way to travel the streets of Boca Grande.

Pine Island is also a potential stop, with the island stretching almost the length of Pine Island Sound. One can navigate around the south of Pine Island past St. James City, where the Caloosahatchee River can be reached.

From there, it’s back home to Cape Coral in one of the many canals.

A barrier island hopping adventure provides variety and gives the hopper a taste of something of everything in which Southwest Florida can provide.

Captiva Cruises’ expertise in navigating the Pine Island Sound and its visits to all the barrier islands is an option. They can be found at or by calling at 239-472-5300.