Explore the tranquil Florida waters via paddleboard at Portofino Island Resort.
1. For the Staycationer
Boasting eight miles of dining and shopping, a water park, tennis courts, cruises on a catamaran and more than 300 two- and three-bedroom Sky Homes within five Mediterranean-inspired towers, you’ll never want to leave Portofino Island Resort. Paddleboard or surf on Adventure Beach, or veg out at the Spa Portofino with a youthful glow smoothing facial and a pick-me-up from the Smoothie Bar. Munch on tapas at the Terracotta restaurant or feast in-suite with the Chef-to-You service. You’ll also find the latest iteration of local favorite Cactus Flower Café serving up California-style Mexican fare. Overnight rates from $305, @portofinoisland
2. For the Down-Home Southerner
Flora-Bama is a local find with national acclaim. When it’s not being written about in Rolling Stone, The New Yorker or Maxim, this dive straddling the Florida-Alabama state line is holding events like its annual Miss Memorial Day Bikini Contest (May 29) or Flora-Bama Fishing Rodeo (June 10 to 12). Whether you’re nibbling on firecracker calamari at the Yacht Club or sipping a Sweetwater IPA at the Ole River Bar, you’ll find a good time with live music and regular events at the Gulf party shack.
3. For the Oyster Obsessed
Dine bayside (minus Zack and Kelly) at this oyster house near Pensacola’s historic Seville neighborhood. A casual alternative to next door’s Fish House, Atlas Oyster House offers Apalachicola Bay and East Bay oysters any way you like, harvested fresh each day. Indulge in a triple chocolate cheesecake or a Fish House Punch. Swing by on Sunday for bottomless mimosas and oysters Rockefeller at brunch. @fishhousepensacola
4. For the Whimsical Reveler
Seville Quarter, a local entertainment mainstay traffics in nightlife and idyll. A menagerie of seven rooms make up this Frommer’s-recommended venue. Be it the Palace Café, Lili Marlene’s Aviator’s Pub, Apple Annie’s Courtyard or End o’ the Alley Bar, Seville puts the whimsy in wanderlust. Sip on a Flaming Hurricane at Rosie O’Grady’s Good Time Emporium, or shoot pool at Fast Eddie’s Billiard Parlor. Don’t leave before you’ve visited Phineas Phogg’s Balloon Works, the two-story dance club found between iron gates from the old Governor’s Mansion in New Orleans. @sevillequarter
5. For the Fickle Foodie
Whether you’re craving a gourmet grilled cheese or a deep-fried avocado taco, Al Fresco Pensacola has you covered. Dine out, literally, at this brand-new medley of food trucks, found under 14 palm trees in downtown Pensacola. Choose from five different menus, including Gunshot BBQ and Fusion World. Relax with a drink and oysters on the half-shell at Shux Oyster Bar at the indoor/outdoor bar on the covered patio.