Destinations

GASPARILLA ISLAND

By the time this reaches your inbox, I’ll already be 24 hours into my stay on Gasparilla Island. If you’ve been following along for a little while then you already know that this isn’t my first time on the island. We took a family trip there last May and enjoyed it so much that we rebooked for the following year before we had even checked out of the hotel. There’s so much to love about this little island but in a nutshell: it’s an easy trip (a quick 2.5-hour flight from Texas!) to a beautiful place with a fabulous hotel, delicious meals, and plenty of activities for everyone in the entire group.  Check, check, check. 

I’ll be taking the week off to enjoy my vacation (follow along!)  but while I’m away, I’m leaving you with my guide to Gasparilla Island. Here, all of my tips and tricks – from where to stay and the dining reservations to book to a list of activity ideas and, to finish it off, a peek at what I packed in my suitcase.

WHERE TO STAY

THE GASPARILLA INN & CLUB

This is what really sealed the deal for us. We loved every bit of our stay at the Gasparilla Inn & Club. Open seasonally from October to July, this historic hotel (it is over 100 years old!) is an ideal spot for a family getaway. With a spa, fitness center, and loads of activities and adventures, the property really checks every single box. It doesn’t hurt that it’s also gorgeous inside and out. 

 

THE BEACH COTTAGES

The Inn has several different options for accommodations – from standard guest rooms to four-bedroom villas – making it easy to find something that suits your needs. We stayed in one of the Beach Cottages. Located just steps from the beach, the beautifully-designed cottages provide an opportunity for a private, “home-like” setting (ideal if you are traveling with children!), while still giving you all of the amenities of the hotel. Our two-bedroom cottage featured an open floor plan that included a dining area, living room, kitchen, and a gorgeous patio that proved to be the perfect shady area for an afternoon game of Rummikub. Each cottage comes with its own golf cart (there’s something so luxurious about a vacation where you never have to set foot in a car) which you’ll use to go most everywhere on the island. 

WHERE TO EAT

THE BEACH CLUB

Located steps from the beach, the Inn’s private club serves poolside snacks and beverages along with a delicious lunch. I love this spot. It’s super easy and the food is really, really good. The menu features all poolside classics – think: club sandwiches, french fries, delicious salads, burgers and more.

THE DINING ROOM AT THE INN

Located in the main building of the Inn, the dining room serves both breakfast and dinner. The dinner menu offers a variety of options, including fresh fish and pasta. (If you’re a fan of Key Lime Pie, be sure to order it here.) What I love most is that it feels upscale but still maintains an unfussiness that welcomes children of all ages – even my rambunctious, sticky-handed two-year-old.

THE PINK ELEPHANT

Affectionately known as “The Pink,” this restaurant features a cozy pub, outdoor patio, and upstairs dining room. It’s a great option for lunch or dinner, and the cocktails are not to be missed. I recommend the Spicy Elephant.

TEMPTATION RESTAURANT

This place is a legend on the island. With framed photos of patrons gracing the walls, this restaurant is every bit as nostalgic as it is delicious. Start with a cocktail in the dimly-lit bar (the people-watching is top-notch here)  and then head into the main dining room for dinner, where you’ll enjoy the freshest fish on the island. Tip: Request the corner booth. It’s cozy and gives you a view of the entire restaurant.

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THE PINK PONY

What is it about being near the ocean that makes ice cream taste even better than it usually does? If you’re in need of a sweet treat, stop by this family-owned spot.  With a rotating menu of ice cream flavors, there’s something for everyone – note: there’s even a “Pup Cup Sundae” for your four-legged friend. 

HATSUNGLASSES

WHAT TO DO

TENNIS TIME

In addition to an outstanding golf course, the Inn’s tennis facilities are also top-notch. They offer clinics for both adults and children along with private lessons by appointment.

GO FISH

I spend no time whatsoever with a fishing rod in my hand but the same can’t be said about the men in my family. My husband and father spend every morning of vacation out on the water and return just in time for lunch to regale us with fishing tales. 

BIKE AROUND TOWN

Other than the ride to and from the airport, we never set foot in a car during our trip. There’s something really nice about vacations like that, don’t you think? During the afternoons, we would bike around town (burning off those ice cream calories!). You can rent bikes (including children’s bikes!) through the hotel.

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THE SPA

The Inn has a lovely spa with a list of services that include everything from a traditional Swedish massage to speciality treatments like acupuncture and crano-sacrial therapy. Pick your pleasure. Note: there’s also an excellent salon should you need a quick blow out or a conditioning treatment after all the sun and salt.

enjoy the happiest hour…

Located at The Inn, BZ’s, with its cypress bar and charming decor, is old-school Florida at its best. It’s the perfect spot to cozy up for a cocktail before dinner. Enjoy one of their signature cocktails (The Last Mango in Paris is definitely a must-try) over a game of backgammon.

WHAT TO PACK

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