Sand Key outside waterfront deck
Sand Key outside waterfront deck

One of the best things about dining out in Florida is the restaurant names. Only in the Sunshine State will diners find places unabashedly called Cooter’s, Crabby Bill’s, Frenchy’s, and Salty’s. Clearwater Beach, a barrier island off the coast of the Gulf of Mexico, is no exception. This walkable beach town offers a wide range of places to eat, from casual surf shacks to fine dining rooms.

What they all have in common (apart from the creative naming) is a sense of fun and lack of pretense. Visitors are more likely to find iceberg lettuce than kale and quinoa, and showing up in shorts and T-shirts even at upscale restaurants is totally welcome. Calorie counting, however, is not. Clearwater Beach offers the chance to indulge in fried grouper, Key Lime pie, and gator bites, to name a few. The dining scene isn’t trendy and that’s the point; this town is all about honest food in an honest setting. Plus, happy hour tends to start very early.


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Here’s where to go.

1. Columbia Restaurant

Hop on the Jolley Trolley to neighboring Sand Key to reach Columbia, a Cuban-American restaurant that opened in 1905 in Tampa’s Ybor City. The restaurant is still family owned, and the menu includes a mix of traditional Cuban dishes like black bean stew over rice, and grilled octopus and chorizo tapas. If you feel like dressing up for dinner, sit indoors; the dining room is decorated with dark wood trim, Spanish tiles, and potted palms. Otherwise, grab a seat on the deck for a casual meal and water views. Waiters will prepare pitchers of mojitos tableside, as well as Columbia’s 1905 salad, which is iceberg lettuce tossed with baked ham, Swiss cheese, green olives, and a dash of Worcestershire sauce. It’s a little salty, tangy, and a meal in itself.

2. Crabby Bill’s


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This neon-lit fishing shack is the perfect place to roll up straight from the beach. At Crabby Bill’s, seafood is the star of the menu — from typical clams and oysters, to the New Orleans-style po’boy stuffed with grouper. Those looking to challenge their threshold for heat can order the Volcano Gator with Inferno Sauce, made with ghost chili pepper. For something a bit cooler, try Crabby’s twist on the hipster staple of avocado toast made with shrimp and feta, served on garlic toast. Happy hour is an all-day affair, starting at 11 a.m. and ending at 7 p.m.

3. SHOR American Seafood Grill

Located inside the Hyatt Regency hotel, SHOR offers a fine dining experience that still manages to be family friendly, and shorts are acceptable attire. Parents will appreciate the children’s buffet, which includes kid-approved staples like chicken nuggets and hot dogs, priced equivalent to your child’s age (so $3 for a 3-year-old, etc.). The adult menu is more sophisticated, with oyster starters and fried calamari made from slabs of giant squid, followed by whole snapper either grilled, fried, or prepared Asian-style in the open kitchen.

4. Post Corner Pizza

Located directly across the street from the new Opal Sands hotel, you can’t miss Post Corner Pizza thanks to its life-size dolphin statue, holding Greek and American flags. Kitsch is all part of the fun at this old school pizzeria. Slide into a vinyl-covered booth and order a Southern breakfast of biscuits and gravy or get into a crispy pizza for lunch or dinner. The Greek salad contains huge blocks of feta and refreshing green peppers.

5. Caretta on the Gulf

Take a stroll to the Sandpearl Resort for a beachfront lunch at Caretta on the Gulf. Bring your sunglasses and settle into an outdoor table, and order a cucumber gin gimlet to cool off. Standout dishes include the oysters, a steak-and-gorgonzola salad, flatbread pizza, and a grouper BLT.

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