The second you cross the bridge over the wide-water-views onto Gasparilla Island, you will be happy. Gorgeous Bermuda-blue water, relaxed vibe, small town, more golf carts than cars, though GI is not golf-centric. The preponderance of carts are populated by a human driver and a canine passenger…charmante! Most of the houses here are in Old Florida cottage style, pristinely-renovated, and none over two-stories tall. Lots of “financial wherewithal” here but almost no ugly McMansions. Also, no crime, as reported to me by two, long-time residents. Soooo relaxing!

STAY

• Gasparilla Inn: beautifully decorated (if you like happy colors, shells and lots of tropical references, which OF COURSE you do!), immaculately landscaped, expensive and worth it. Here’s the façade (below):

•  The Innlet: less expensive (by more than half) affiliate property of the Gasparilla Inn. The reason its less is twofold: (1) The décor is simple & not as stylish as the GI & (2) It is farther away from the center of Boca Grande, but not by much. While I have only viewed the rooms on the website, I have seen the outside in person, which is neat and cheery.
• Rent a house via Parsley-Baldwin Realty (1-800-741-3074) in the historic district, where they’re prettier and the walk into town is short.

SEE THE SIGHTS

• The beach–long walks on white sand, good shelling, no building over two stories, really low-key
• The town…the only town…on Gasparilla Island is called Boca Grande. It is tiny, quiet and very cute w/charming houses. Walk down Banyan Street to see the 100-year old Banyan trees–so evocative!

• Bike the trail that runs the length of the island (more interesting riding around town and south) and to the two lighthouses at the south end, especially Port Boca Grande Lighthouse (circa 1890) & its museum.

• Boating/fishing: Boca Grande is known as the “tarpon capital of the world!”
• Boca Grande Historical Society Museum : very small but interesting.
• Golf: four courses.
• The Boca Grande Community Center offers good lectures, yoga, and a small fitness room. During the week we were there, the CEO of the National Geographic and a railroad history expert spoke. In addition, a recorded performance of the Broadway play “War Horse” was being shown in its auditorium.

EAT, DRINK & BE MERRY

•  The Gasparilla Inn (500 Palm Ave.): pretty, old-fashioned dining room with sophisticated tropical décor. Food is good. Go to the Inn’s attractive bar for your pre-prandial libations!

• The Temptation: very good food and Old Florida ambience, friendly bar and two adjacent dining rooms. The best DR is the front one, with uplighting on its blue walls painted with old Florida scenes=retro and transporting. It is waaaay more fun than this photo conveys!

• 3rd Street Café (Third St. & E. Railroad Ave.): Sometimes excellent and other times unremarkable food here, but I like it a lot. Eat in the outdoor courtyard with its pretty banana leaf/palm tree garden, up-lit dramatically. It has a small attractive bar and good service.
• South Beach Bar & Grille (777 Gulf Blvd.): GREAT place to watch the sunset. This is a simple, non-fancy restaurant on the beach all by its lonesome…no competition and no need for it. Go to the bar, buy your drink, and toddle on out to the Adirondack chairs as you watch the sun go down. Very peaceful!
• Gasparilla Island’s signature cocktail is the Hummer, made with vanilla ice cream, Kahlua and Rum. It is not listed on all drinks menus but ask the bartenders. They’ll know!

SHOP IT

• The Palm on Park (444 4th St.): Lilly! Need I say more?

• Grapevine Gourmet & Gift Shop (321 Park Avenue): excellent carry out cocktail food, PLUS really attractive ceramic dip-bowl-attached-to-plates, like Lilly Pulitzer would’ve used to serve Fritos and onion dip.
• The Inn Boutique (at Gasparilla Inn) has a good selection of pastel beach dresses, tops and pretty jewelry (e.g., Meg Carter)
• The Gasparilla Inn hosts frequent trunk shows open to guests and non-guests, alike.
• The Patio Shop at Fugates (4th St. & Park Ave.)–is chocked full of cheery resort wear and cheery staff to match.
• Newlin’s (446 4th St.)–upscale carry out (one entrée per day is made and residents reserve them in advance; when I was there, they offered chicken pot pie, coq au vin, shrimp and grits) plus attractive dish ware for purchase.

Of Note: This is a happy, fun place. The natives are friendly. It is small. Few street lights at night and few cars, too. It can be dark walking back from dinner but that makes it easier to peer into the cozily lit-up houses (so MANY attractive tropical-cottage-style houses). No crime here, so the darkness is not spooky. If you like a go-go pace, this is not for you. We spent two, relaxing weeks here, never bored.