Keep Cool with Naples’ Hottest Poolside Bars

It’s the essence of Florida living: the ability to grab a chilled beverage and hang out poolside. And with the seasonal crowds gone, this pastime is even better in the summer. These four locales excel in food, drink, and ambiance.

1. Island Gypsy Poolside Café

Restaurateur Jerry Alajajian, who also owns the Island Gypsy Café & Marina Bar, transformed this spot in the Park Shore Resort earlier this year. The lush, tropical atmosphere is enhanced by a menu that features everything from peel-and-eat shrimp to filet mignon. Relax with a flavored piña colada or a gypsy punch (light and dark rum, brandy, schnapps, and fruit juices) and find out why this place is “locally world famous.” 

2. Gulf Coast Oasis Pool Bar

The Baja-influenced cuisine at this poolside retreat in the Naples Grande Beach Resort includes chicquitos (guacamole, nachos, and Southwestern egg rolls), plus sandwiches, salads, tacos, and bowls. Registered guests can wash it all down with a tropical drink or a mocktail and luxuriate on the terrace or in the privacy of a cabana or lounge chair. 

3. Pool Bar at Edgewater Beach Hotel

Who says poolside fare can’t be healthy? This pool bar slings items from the hotel’s Coast restaurant kitchen, with some dishes inspired by the Blue Zones Project, a community-led wellness initiative. Try the meze platter (roasted garlic hummus, local crudités, feta, country olives, and warm pita chips) paired with a “skinny” blueberry lemonade or a shaken agave limeade. 

4. Harold’s Place

One of Naples’ best-kept secrets has been tucked away off Tamiami Trail North for 33 years. On any given afternoon or evening, locals congregate at the chickee bar for carefully crafted tiki cocktails accompanied by burgers, smoked fish dip, Gulf oysters, and quesadillas. Indulge in happy hour Monday through Friday from 4 to 7 p.m., and don’t miss karaoke every Sunday from 3 to 7 p.m.

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