Pine Island Sound Spotlight

by  ShermansTravel Editorial Staff | May 4, 2009
Pine Island Sound Aquatic Reserve, Florida
Pine Island Sound Aquatic Reserve, Florida / Photo courtesy of Florida Department of Environmental Protection

By: Sam Sifton

It takes about an hour to drive from the Fort Myers airport up into the scrub pine and woozy humidity of Pine Island, off Cape Coral, and by the time I get to the bridge at Matlacha, about halfway along in the journey on Route 78, I discover my pulse slowing and the stresses of workaday life drifting away on the tide. Seasonal blues? Before long, I’ll be skipping across the ruffled waters of Pine Island Sound in a water taxi, bound for the quiet elegance of North Captiva Island, 5 miles offshore.

And when the sun falls that evening, I’ll be on the beach for the spectacle, staring, happy and relaxed, from a varnished chair, out at the Gulf of Mexico, just steps from a beautiful rented home on an island that has no stop signs, no streetlights, no cars. My wife will smile as the kids run first into the low surf and then up toward the dunes, soaked and laughing in the fading light, again and again. I’ll be better than fine.

For some, travel in Florida is duty. For others, it’s compromise: old relatives in Vero Beach, drunken revelers in Key West, society scenes in West Palm or Hobe Sound, screaming children in Orlando. It’s something to be done, and if it’s watching spring training baseball or lying out on Miami Beach for a weekend, it might even be enjoyable. But a great travel destination? Florida?

Yes. For more than a decade now I’ve been traveling with my family to the peninsula’s southwest coast to explore what remains of old Florida—as much a state of mind as an actual place on a map. We’ve sailed charter boats on the Intracoastal Waterway from the Caloosahatchee River in Fort Myers, north through Charlotte Harbor and into Gasparilla Sound, anchoring at night in quiet lagoons, elegant marinas, and on rowdy docks alike. We’ve punted around the backwater of Estero Bay and the coves behind Marco Island, throwing lures and bait at redfish and snook under the watchful eyes of gulls, pelicans, and bald eagles. We’ve stayed in luxury condominiums on Sanibel Island and old-timey cabins on Captiva, in the coddled suites of the Ritz-Carlton Naples and in less extravagant circumstances along the Tamiami Trail.

And the region continues to make its siren call. We’ll get to luxury in a moment and we’ll enjoy it. But it’s important to note right from the start that old Florida is still out there on the southwest coast, beautiful and pungent under the bright-blue sky: Cracker-style homes set high above the flood-prone earth, rust-stained fishing boats, comfortable wicker chairs, roseate spoonbills, and sweet white shrimp.

The islands of Pine Island Sound, such as Sanibel and Captiva, are a good place to start a visit to the region. Pick any one as a vacation base; as with choosing varieties of steak or ice cream, it is difficult to go terribly wrong. Located just west of Fort Myers, the islands include a low-lying chain of barrier sandbars on the leeward coast of the Gulf of Mexico, shaped like a waning crescent moon, or a shrimp. Long a refuge for piratical sailors and, more recently, smugglers, Sanibel has been connected to the mainland since 1963 by a long causeway over San Carlos Bay, and Captiva to Sanibel by a short bridge over Blind Pass. North Captiva, which has always been divided from Captiva by scrub forest, became completely severed from its sister in a 1921 hurricane that created Redfish Pass. Smaller, interior islands like Cabbage Key and Useppa have likewise been battered by storms over the years.

Their resilience in the face of natural disaster is part of the region’s charm. Still, it’s best to travel to southwest Florida after the hurricane season passes, at the end of November. Hurricanes are like Christmas, as they say down there. At some point, you’re going to have a tree in your house.

View our Pine Island Sound Slideshow by photographer Annie Schlechter for glimpses of Florida's family-friendly southwest coast.

Cabbage Key

A high point of any trip to the islands is a visit to Cabbage Key, a 100-acre island off the northwest coast of Pine Island accessible only by boat or seaplane and where, in the 1930s, the family of the mystery novelist Mary Roberts Rinehart built a concrete and coquina-shell homestead atop a Calusa Indian shell mound. In 1944, the Stults family turned the place into a lodge, and people started tacking dollar bills onto the walls and ceiling of the bar, which has since taken on all kinds of pop-cultural baggage: Cabbage Key has been cited both as an old Hemingway fishing hangout and as the location of the original cheeseburger in paradise, immortalized in song by Jimmy Buffet. (Similar claims about both men have been made at bars and lodges across the state and throughout the Caribbean, of course. Tall tales are a hallmark of old Florida as well!)

Regardless, it is indeed a kind of paradise to take a water taxi to Cabbage Key from Pine Island or Captiva for lunch or dinner, to sit under palm and royal poinciana trees, drinking beer and eating that meal as a barge steams past in the channel or a charter captain expertly maneuvers a 50-foot yacht into a 52-foot boat slip, and then to nap, or kayak, or fish, with no more thought of what might come next than the humble manatee rubbing hard against the rough pilings on the dock.

Where to Eat
Looking for that cheeseburger in paradise? Find it in the bar on Cabbage Key (Mile Marker 60; 239/283-2278).

Captiva Island

Don't miss the charms of the ’Tween Waters Inn (from $180/night;, at Captiva Island’s narrowest point, steps from both a sound-side marina and a wide Gulf beach. Established in 1931, the resort offers magnificent little seaside cottages, which have played host to presidents, novelists, and naturalists alike over the years, and a terrific bar and restaurant where we have enjoyed winter barbecues to rival anything put forth in the Carolinas. More purely luxurious, the South Seas Island Resort (from $500/night; on Captiva has been extensively renovated since taking the brunt of Hurricane Charley in 2004, and is a lovely family-friendly destination for those for whom relaxation is not enough. Indeed, for the tennis and golf obsessed, it’s a must not to avoid.

Read our Sanibel and Captiva Island Travel Guides for even more in-depth destination and trip-planning advice!

Sanibel Island

Down on Sanibel, hotels and resorts abound, but the point of the place is best captured in two activities. First, conspire to be on the island during a proper low tide, when you can walk along the deep shoreline looking for shells pushed ashore by the prevailing breeze and passing currents. Locals call it the Sanibel stoop, and it is a wildly addictive sport. (Field guides to the shells are to be found everywhere, from the lowliest inn to the most luxe suite in the county.)

Second, there are few more enjoyable jaunts in the region than a trip to the J.N. “Ding” Darling National Wildlife Refuge (, a giant tract of undeveloped mangrove hummocks on the island’s southeastern coast. Named for Jay Norwood “Ding” Darling, the Pulitzer Prize–winning cartoonist for the Des Moines Register and Tribune and a noted conservationist, the refuge is home to a spectacular number of migratory birds and indigenous wildlife (yes, that’s an alligator in the distance) and visitors can explore it by bicycle, kayak, canoe, or car.

Where to Stay
Great value may be found at the Casa Ybel Resort (from $300/night; on Sanibel, a secluded hotel on 23 acres of beach at the southern end of the island. Founded in the 1890s, the hotel has a terrific pool, newly renovated one- and two-bedroom suites, and close proximity to a 14-mile length of white-sand beach, home to some of the best shelling in the world.

Where to Eat
Sweet Melissa’s Cafe (751 Tarpon Bay Rd., 239/472-1956) features a menu of fresh local fish and tapas-like offerings in a casually elegant room. Also on Sanibel, Doc Ford’s Sanibel Rum Lounge (975 Rabbit Rd., 239/472-8311) serves excellent Gulf shrimp in a sports-bar atmosphere not nearly as loathsome as that adjective usually implies. 

Read our Sanibel and Captiva Island Travel Guides for even more in-depth destination and trip-planning advice!  

North Captiva Island

For anyone who wishes to understand the draw the region had on Hemingway, Theodore Roosevelt, and all the other notables who made the then-difficult journey in the first half of the 20th century, the place to head to is North Captiva.
Most of the southern end of the island is a protected wildlife refuge. Walking North Captiva’s sandy edges as birds pinwheel overhead and dolphins feed in the surf, it is possible to imagine life as it was 400 years ago in Florida—a land unspoiled by human hands. The town, such as it is (only 300 homes) is found at the island’s north end, a verdant settlement divided only by a short, grass airstrip. Many, if not most, of these homes are taken care of by management companies and are available for rent; when we visited in the winter, early in 2009, there was only about a 40 percent occupancy rate, which meant that there were both deals and increased solitude available for the prospective tenant.

After our arrival from Pine Island, which is a 40-minute taxi ride from the Fort Myers airport and where a regular ferry service to North Captiva originates, we checked in at the dock maintained by the North Captiva Island Club. The club handles rentals for many of the houses on the island and provides an ersatz village square for visitors: You get your golf cart there, swim in the pool, play tennis, take a kayak out into the sound—all this is included in your house-rental fee. Keys were handed over, and a pleasant fellow offered to take our bags to our home. We had a lovely breakfast at Mango’s next door to the club, investigated the tennis courts and pool, then took a short and silent drive along a sandy path to our vacation residence, a gem on stilts that offered a magnificent view of the Gulf.

We found the refrigerator filled with groceries we had ordered ahead of time and charcoal on the grill outside. The pool gurgled and soft winds rustled in the fronds of palms, out front, out back, all around. There was swimming to be done, a long walk to take on the beach before dinner, and a movie to watch before bed. My wife and I set our bags down in a plush bedroom with 120-degree views of the island and the Gulf and started to laugh. Who knew paradise had a ceiling fan?

“Come on, Mom and Dad,” our daughters called, already in bathing suits, urban doldrums receding behind them, and eager to swim. “Let’s go!”

Where to Stay
Renting lodging from the North Captiva Island Club Resort ( can be either a smart splurge or a great value, depending on the home’s size, location, and amenities. A five-bedroom home located on the Gulf, with a pool and a gourmet kitchen, starts at about $5,500 a week. A two-bedroom home with a pool and incredible views of the Gulf, and located only a short walk from the beach goes for $2,500 a week.

Where to Eat
A dessert in the ticky-tacky brilliance of Captiva’s Bubble Room (15001 Captiva Dr., 239/472-5558) would not be an error, though those who dislike kitsch would be wise to avoid the place entirely. 

Read our Sanibel and Captiva Island Travel Guides for even more in-depth destination and trip-planning advice!  

Island Hopping in Your Own Boat

There is perhaps no better feeling than that of cruising the waters of Pine Island Sound from atop the bridge of your own boat and floating home. For those who agree and have moderate or greater experience piloting boats larger than 25 feet, a smart splurge is to rent one from Southwest Florida Yachts in North Fort Myers. The company offers a selection of beautifully maintained luxury trawlers and sailboats available for charter. Take a Grand Banks 42 ($4,500 for the week, plus $200 a day if you’d like a licensed captain onboard to teach you the ropes; down the Caloosahatchee River toward the Gulf of Mexico and turn north along the east coast of Sanibel. Spend an evening in the shallow waters of Tarpon Bay, then head north again along the Intracoastal Waterway for lunch at the clubhouse on Useppa, an elegant private island that provides charter captains courtesy docking. Pass another evening at the ’Tween Waters Marina on Captiva or off Gasparilla Island on the far side of Charlotte Harbor. Head home slowly, with the wind in your face, and make sure to stop whenever you wish to swim, fish, or just drift on the tide.

Less elegant perhaps but roomier and delivering a great value are the Gibson houseboats available for charter through Holiday Cruise Yacht Charters in Fort Myers ($2,400 for the week;

Getting There

The southern tip of Sanibel Island is a 40-minute drive from Fort Myers. Travel logistics will vary depending on the destination. Those visiting Sanibel or Captiva may wish to rent a car; travelers to North Captiva or Cabbage Key need only hire a taxi from the airport to Pine Island and then hop on a Island Girl Charters (; 239/633-8142) ferry from Pineland Marina. One might begin a trip to the area by spending a night at Pineland’s marvelous Tarpon Lodge (from $140/night;, a 1926 pile with views of the water and rooms steeped in the history of old Florida.

When to Go

Peak season, when temperatures hover in the mid-70s, runs from the end of December through early April. Rates drop at the end of April and temperatures creep into the 80s. Hurricane season begins in June and ends in November. Storms are most common in September and October.

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