~ John Wanamaker
| Location | Gasparilla Island, Florida |
| Type | Seaside, village |
| Distance | 14 miles, walking and biking, plus strolls to good food |
| Highlights | Beaches, shells, great food, jumping manta rays, and family time |
| Duration | Three days, two nights, or keep walking 'round and 'round. |
| Difficulty | E |
Ever walked on a beach and wanted to keep on walking? No turning around to retrace your steps? On an island, you can do it. And on Florida’s pristine Gasparilla Island, you can do it on gorgeous white sand, stop to snorkel in crystal clear gulf waters, sort through
obscenely big piles of shells for prime specimens, watch marine biologists document sea turtle nests, and catch glimpses of leaping manta rays, dolphins, and giant tarpon. Once you make it to the island’s town of Boca Grande, you can shop at hip boutiques, eat real cuisine, not to mention home-made ice cream, and stay in a roomy ol’ downtown inn.

For our family, everything seemed a bit more special because, well, we were on an island. Gasparilla is small and removed, with the slow-paced, easy-going attitude that makes for an ideal vacation-escape ambiance; an escape that in our case was not only from the world, but from the car. Fresh off the heels, so to speak, of our decidedly urban walking adventure in Dallas we were looking forward to the possibilities of a two-day walking and pedaling trip around the island. Just an hour’s drive from Sarasota, across a sequence of bridges connecting an archipelago of smaller islands, Gasparilla has long been a special spot. Back in the day there was a full-service, non-stop train to and from New York, servicing a wealthy clientele who succeeded in ensuring that development on the island is all but locked down and devoted to private residences. No high rise hotels here, thank you very much.

The Island House Inn at The Boca Grande Resort is the only hotel at the north end of the island, but we found it had exactly the amenities needed for an ideal starting point for our journey. There was a fine swimming pool where we relaxed the night before our trek, and a general store where we bought our sandwiches for our upcoming picnic. The next day, we were rested, well-supplied and positioned just right for our island circumnavigation. We set off our first morning walking up the bike path to the foot of the bridge that entered the island from the east. We then turned north, and respectfully picked our way over private dock walkways for about 200 yards before getting to the unobstructed beach. From there we walked around the northern point of the island, then set off down the western coast.
And oh, the shells. Now, we knew this section of the gulf is famous among beachcombers, but were stunned at the obscene piles of shells piled up at the island’s northern point. As foot-travelers, we had to be discriminating. But that just means a stronger collection, right? No regrets. Really.
We weren’t carrying camping gear, but even a relatively light load on your back also helps you appreciate something else: the pleasure of taking it off. I’ve never had breaks as delicious as these. Drop the pack, toss the straw hat, shed the shirt n’ shades, and do the plunge. As sweet and cool as a glass of southern iced tea. Break out the snorkels, stick the umbrellas in the sand, spread out the sheet, lay out the picnic, and get ready for yoga, ‘cuz it’s a party. A party so good that day-old pizza gets crowned “the best pizza I’ve ever tasted,” and just sitting in the shade and floating in the water become vividly sensual experiences. On our way to town we had four such parties.
About two thirds of the way down the island we turned inland from the beach, and in just four blocks we’d reached downtown Boca Grande, and the Anchor Inn, our bed for the night. It’s one of the town’s original old houses, and is set up perfectly for a home-style stay. We had a two-bedroom, 1.5 bath suite with a full kitchen, front & back porches, a deck, and a cute little pool in a nicely gardened area. The wife and I sipped beers while the kids played in the pool and we all reflected on the achievement of our hike. Then, refreshed and relaxed, we dressed for dinner.
We celebrated our fifteenth wedding anniversary that night at one of the island’s best restaurants, “The Temptation”, and had one of those meals you keep returning to in your mind to savor again. In particular the pan-fried snapper with lemon, garlic, and apple juice scored high in the gustatorial category when we later recalled the trip’s highlights. The kids’ pan-fried grouper “fingers” from the children’s menu? Having “helped” eat them, I can tell you, those are happy meals.
The next day we rented beach cruiser bikes from “Island Beach ‘n Bikes” and cruise we did. We first went south to finish traveling the length of the Island, stopping at Gasparilla State Park to see the lighthouse and museum, which nicely describes the local nature and history. Then it was back to town for lunch at The Loose Caboose, which included excellent homemade ice cream, by the way. Finally, that afternoon, we biked back to our car at the island’s northern end. (We’d arranged to leave our bikes there where Beach ‘n Bikes would pick them up later.) Every bit of the way was on a beautiful bike path often lined with palms, and which skirts the hanging roots of banyan trees. Here and there are strategically placed benches overlooking the bay. Now that’s easy-going, vacation bicycling.
And even though it had been fun every step and pedal of the way, when we finished, we were proud. O.K., so we hadn’t circled Australia, or climbed Everest, but we definitely DID Gasparilla.
Eat/Sleep/Do

Planning: Lee County Tourism Info
The Boca Grande Resort: www.thebocagranderesort.com/
The Anchor Inn: www.anchorinnbocagrande.com/
The Temptation Restaurant: http://temptationbocagrande.com/
Editor's Note: The Demeraths' trip to Gasparilla was capped by the successful capping of the gushing BP oil well in the Gulf - just another occasion to celebrate the many upsides of car-free travel...
(all photos by the Demerath family)