by Sheila Gaspers

For over 100 years, the wealthy and privileged have migrated like geese to lovely Gasparilla Island to escape from the cold harsh northern winters. This small, seven mile barrier island, named for legendary pirate Don Pedro Gaspar, is a one hour drive from both Sarasota and Fort Myers. It is an eco-rich paradise in Southwest Florida nestled between Charlotte Harbor and the blue-green waters of the Gulf of Mexico. Here you will find world class fishing, kayaking, sailing, birding and miles of pristine white beach.

The historic village of Boca Grande is the official center of the island. The town’s origin dates back to the arrival of the railroad in 1907. The original train depot has since been converted into a restaurant and the tracks were transformed into the island’s current day trail system. The main street area, just two blocks square, is bustling with activity during “social season” (late October to April) when the seasonal residents and loyal guests return for an extended holiday.

Fun Fact: The Boca Grande Zip Code is ranked among the top 125 most expensive zip codes on Forbes’ real estate list.

There are no stop lights, no high rises and no chains. As one local phrased it nicely, “We are the other Boca. Most folks don’t know where we are and we like it that way.”

Downtown you will find eclectic shops, high end boutiques, art galleries and some of the best seafood in the country. In fact, word spreads fast when the shrimp fleet comes in. Be forewarned; your only clue is a simple sign that reads “Fresh Local Shrimp Today”. Follow the crowd to uncover the boat location before the catch is gone (insider tip: check out Whidden’s Marina).

On Boca Grande, life slows down and pleasure schedules follow island time. Rounds of golf, bridge at the club, an afternoon swim or a bike/golf cart tour around the island are daily distractions. The grueling 9-to-5 office grind and the stresses of every day big city living are soon forgotten. The only traffic jams experienced will be the occasional line of golf carts, often with dog in tow on the passenger side, headed to Hudson’s, the local grocery, for a cup of coffee and a copy of the Boca Beacon newspaper.

Boca Grande golf carts are in a luxury league of their own. A tricked-out ride is the ultimate status symbol. Custom cart body styles include Mercedes Benz, Cadillac, Jaguar, Bentley and the occasional Rolls-Royce stretch-cart limo. Not to worry, you can join in the fun. Cart rentals are readily available.

The Grand Dame of the Island is the majestic Gasparilla Inn and Club. This year marks its 97th season as one of Florida’s most celebrated historic hotels. The resort property has been the host to Presidents, celebrities and dignitaries. You have your choice of a deluxe room, superior suite with balcony or private cottage accommodations. All 140 rooms have been beautifully restored and exemplify Old Florida elegance.

The Gasparilla resort’s magnificent 72 par, 18-hole Pete Dye Signature golf course covering 106 lush green acres on an adjacent island and the Boca Grande Pass’s reputation for world famous Tarpon fishing have heightened the destination’s claim to fame.

If there is no room at the Gasparilla Inn, you will find a wide variety of other overnight options from house rentals to quaint family owned hotels. The Anchor Inn is a gem, just down the street from Gasparilla. Built in 1925, this historic property is a beautiful example of classic Florida Cracker architecture. The Inn offers affordable one and two bedroom apartment style units. Each unit has a full kitchen, wireless internet and access to a private garden pool. Bright and airy Corner Unit #4, my personal recommendation, can easily accommodate a family of four.

Foodies will not be disappointed. Culinary delights await you. The Gasparilla’s Pink Elephant Restaurant is a favorite offering a casual dining and family friendly experience. The Hog Snapper entrée, a mouth watering signature dish, will tantalize even the most discerning of palates. A free local marina, just steps away, also provides boaters easy access. All agree that it is one of the top picks to watch the sunset over the bayou.

Other fun local dining spots include Sisters Restaurant, offering the some of the best pizza and burgers in town; Third Street Café, a popular breakfast eatery; and South Beach Bar & Grille, the only public seafood restaurant on the beach with incredible daily all-you-can-eat specials and a spectacular view.

Happy Hour at the The Temptation, a timeless watering hole, is a tradition that should not be missed. On any given day, you will find local fisherman chatting with blue blood aristocracy at this Boca Grande treasure. The “Moscow Mule”, a vodka and ginger beer concoction served in an ice cold copper mug, is the libation of choice to mark the end of a perfect beach day.

Step back in time with a visit to the Port Grande Lighthouse on the south end of the island. The lighthouse museum exhibits offer a glimpse into the colorful past dating back to the Calusa Indians, the island’s earliest inhabitants. For a complete history lesson, spend a few hours in the Boca Grande Historical Society Museum on the corner of Park Avenue and Banyan Street.

Ladies, be sure to pack the pearls and the Lilly Pulitzer. And gentlemen, don’t forget your evening dinner jacket. The A-list crowd always has a dress code and you don’t want to miss out on a gala or dinner party.

Whether you come for a day, a week or the entire season, this little island will leave you with big memories and will beckon you to return for more.

About the Author:
Sheila is a freelance writer who has crossed the country and the continents to connect to the people and places that will inspire and re-ignite one’s passion for living. Her stories have been published in print and online domestically and internationally. Her successful media and business career spans thirty years. But her discovery that the climb up the corporate ladder could be spiritually crippling, she changed her course. “The view is so much better when you are grounded with eyes wide open.” True to her gypsy heart, Sheila reinvents herself daily and follows her dreams. A storyteller, historian, entertainer and true soul sister – this travel diva can’t wait for her next gig. Did someone say “TV Talk Show Host” or perhaps “Cruise Director”?