More Photos (4)

Driving over the single-lane swing bridge connecting Boca Grande to mainland Florida, I always feel my New Yorker blood pressure drop. Arriving at this Gulf of Mexico barrier island is like going back in time; its understated peacefulness has kept me coming back at least once a season for my whole life. The old-Florida feel of Boca Grande’s Gasparilla Inn & Club, built in 1913, inspired its motto: Florida as it was meant to be. Even its name has historical significance: José Gaspar was an 18th-century Spanish naval officer turned pirate who was attracted to the small but beautiful place.

An ideal spot for families, the majority of visitors to the Gasparilla Inn have been coming for multiple years—often for multiple generations. Guests can choose to stay in the plantation-style main inn or follow the lead of President Bush’s family (#41 and 43), and get their own separate cottage on the grounds.

The Inn’s 137 rooms are divided between the three story main building and seventeen cottages on the property. Rooms range from small but practical, ground-floor twin rooms that harken back to the inn’s original set-up, to more spacious suites with sitting rooms and dining areas. Room service is available throughout the day and all rooms have a mini-fridge and Keurig coffee makers. Guests looking for a bit more privacy and freedom have the option of taking a room or two in a cottage, or an entire cottage (which consists of two king-sized rooms and two twin rooms, all en suite.) The cottages also include two lanais (a Florida-specific term for a screened-in porch) and a spacious sitting room.

A member of the National Register of Historic Places, the Inn has rooms that feel like your grandmother’s beach house—if you grandmother is very preppy and chic. Rocking chairs on the main porch greet arrivals and the doors open to a carpeted hallway lined with potted palms and display shelves of seashells. Pink-and- green botanical prints hang on yellow-and-white-striped walls and Tempurpedic beds have white rattan headboards. All rooms and cottages were recently renovated so while the furnishings lend an old-fashioned allure, they are all new: bathrooms have stand-alone, molded radiators (which are rarely turned on), but also chrome accessories. Doors are opened with real keys, not magnetic keycards, but WiFi is available throughout all the rooms and cottages.

Days are spent in Lilly Pulitzer and tennis whites. Activities through the Club range from highly active to stationary and relaxed. Tennis can be booked on the seven clay courts, golf is available on the Pete Dye-designed course, guides are ready to take anglers sport-fishing in the Gulf or the harbor (Boca Grande is the tarpon-fishing capital of the world), and the island has even caught on to the trendy new aquatic activity: SUP (stand up paddle-boarding.) For a more relaxed day – in or out of the sun – I love to play backgammon and croquet, visit the spa, swim and sun-bathe by the two pools and magnificent Gulf, and visit the beautiful Spanish-style Johan Fust Community Library (1040 W. 10th and Gasparilla Road) and its serene courtyard. The spa offers massages and facials a serene lap pool, Jacuzzi, steam and sauna and a hair and beauty salon. There are Yoga, Zumba and Pilates studios, and the gym overlooks the ocean. Indoor and outdoor lounge areas are luxuriously comfortable and worthy of a visit.

Bikers and golf carts most definitely have the right-of-way on the island. The Inn can provide airport transfers and arrange for bike, golf cart, and rollerblade rentals for transportation around the island, eliminating the need for a rental car. The island-long bike- and golf cart-paths built on the old railroad tracks, have a paved lane as well as a sand lane for joggers. Other modes of Boca Grande touring can be arranged including those by seaplane, chartered boat and kayak.

Visitors of all ages can go shelling on the seven miles of white sandy beaches, hunting for the rare tulip shells and sand dollars and ending at the iconic Boca Grande Lighthouse. The island is also home to such wildlife as sea turtles, manatees, ospreys, pelicans, great blue herons and white ibis.

Guests have the choice of à la carte or all-inclusive meals, with breakfast and dinner in the inn’s dining room or Pink Elephant restaurant and buffet lunch at the Beach Club. Highlights include weekly seafood buffets, afternoon tea in the lobby and breakfast in the dining room (in particular the oatmeal pancakes with lingonberry compote). While parents linger over dinner in the Inn’s dining room and enjoy cocktails in BZ’s or the Pink Elephant (try the White Russian-meets-milkshake cocktail), kids and teenagers can play billiards and ping pong in the game room. On Bingo Nights whole families rally together in the grand ballroom for the much loved and eagerly anticipated “stand-up-bingo.”

Surprisingly, the sleepy island has some good shopping: Fugate’s (428 4th Street West; 941-964-2323), a 1930’s-era drugstore-turned-boutique, sells everything from Jack Rodgers to The New York Times and sunscreen. Ariel Ltd. (444 4th Street; 941-964-0480) and the Inn Shop offer a variety of beachwear and accessories. Boca Grande-logoed belts and hats as well as supplies can be found at Boca Grande Outfitters (375 Park Avenue; 941-964-2445). When I’ve finished strolling the three streets making up the town, I treat myself to a homemade ice cream cone at the Loose Caboose (433 W 4th Street; 941-964-0440), housed in the former train depot.

The Inn is open from October to July and can take parties of up to eight guests. Rooms from $250 per night. Contact our Bookings Team for help planning a Boca Grande retreat.

Getting There: Many airlines fly to Tampa (2 hr. drive to Boca Grande), Sarasota (1.5 hr. drive to Boca Grande) or Ft. Myers (1.5 hr. drive to Boca Grande) and the Inn can provide transfers. International flights fly to Orlando (3.5 hr. drive to Boca Grande).

When to Go: October through May

Perfect Length of Stay: 3-6 nights

Who Should Stay: Active or beach-loving families with kids ranging from infants to teenagers. Families traveling with pets; dogs are welcome in the cottages.

Who Should Not Stay: Those looking for a sleek and cool Miami or even Palm Beach experience. And anyone interested in a wild nightlife will be bored here post-10pm.

Indagare Tip: Take a sunset bike ride through Banyan Street and down to the lighthouse.

Rooms to Get: Rooms on the 2nd floor of the Inn, or any of the cottages.

Don’t Miss: Visit nearby islands Cabbage Key and Cayo Costa by boat. Guides can even motor down to the Florida Keys, about three hours each way.