The No. 1 Resort in Florida Is a Charming Family-owned Inn With a Private Beach Club

"I'm at the age where I attend at least one wedding every quarter. As a result, I've gotten used to securing the last spot in a group Airbnb or splitting a stay at a large hotel chain. But when I checked into The Gasparilla Inn & Club in Boca Grande, Florida, for the nuptials of my wonderful friends Teddy and Amanda, it was clear I was in for a completely different experience."

"On our first night, my partner and I headed to BZ's, a charming bar tucked off the main lobby, for a pre-welcome drink. The Kentucky Derby was being held in Louisville that same weekend, so, to celebrate the event, the space was anchored by a frozen ice sculpture of a horse, with pink and yellow fascinators everywhere I turned, and a whole lot of martinis being poured. The classic energy spilled well into the weekend."

The Gasparilla Inn & Club occupies a grand Old Florida-style columned manor that first opened in 1913. The resort emphasizes nostalgic, classic formality with an enforced dress code and attentive uniformed staff who often greet guests with hello ma'am. Social spaces such as BZ's bar feature island-inspired decor and festive events. Ceremonies can take place on the hotel's golf course overlooking Charlotte Harbor, with celebrations extending to a beach club reached by golf cart at sunset. The property offers 163 accommodations including suites, cottages, villas, and estate homes, and guest rooms feature bold colors and island-patterned textiles.

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