Location, Location, Location

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From feasting on the flakiest snapper with fresh mango slaw to raising a salt-rimmed margarita made with local limes, nothing makes dining better than a breeze on your back and a view of our aquamarine-toned waters. If you know where to look, there is no shortage of Gulf-side bistros, laid-back bars lining canals and stilted bungalows along bays.

If you find yourself on resort row on Marco Island, you owe it to yourself to dine at Sale e Pepe, one of the region’s most romantic restaurants. The Marco Beach Ocean Resort takes its flagship restaurant so seriously, Sale e Pepe has its own separate driveway and valet—and a 500-bottle wine list. The Italian chef’s reinventions of classic dishes from his homeland sing—especially the seafood stew and the sea bass with stewed clams. Sit alfresco on the spacious fan-covered terrace and dive into perfectly al dente linguine and a glass of pinot grigio.

Just north of Marco Island, chef AJ Black, of Sanibel’s former Il Tesoro fame, gutted and rebuilt longstanding The Blue Heron restaurant on Johnson Bay, reshaping it into Isles of Capri’s finest casual dining experience. Opened in 2020, Osteria Capri overlooks bobbing boats on serene backwaters from its intimate, windowed dining room with a spacious patio and full bar—the latter a new addition. The chef imports his flour from Italy and sources organic greens and other products locally to produce house-made pastas and Italian classics, such as whole-roasted branzino, lamb osso bucco and braised beef short ribs with gnocchi.

Unsurprisingly, Naples has more than its fair share of waterfront options, from mangrove-perched standout The Bay House, which overlooks the Cocohatchee River, to Bayside Seafood Grill & Bar in The Village Shops on Venetian Bay, which feels like you’re canalside in Italy. If you want the experience of curling your toes in the sand while dining, check out The Turtle Club on Vanderbilt Beach. Another more upscale option is BALEEN at LaPlaya Beach & Golf Resort. From breakfast to dinner, the menus are divine and the experience is always memorable (they even have fire pits on the beach at night). For sweeping vistas of the Gulf, Gumbo Limbo in The Ritz-Carlton, Naples, goes above and beyond with an ever-changing menu and clever cocktail list, served from its beach-shack-style perch just above the sand.

At Naples’ BALEEN, guests can head to the beach after dinner to sit around the fire pits. (Courtesy LaPlaya Beach & Golf Resort)

In Fort Myers, there weren’t many places to dine on the waterfront until Luminary Hotel & Co, part of Autograph Collection, landed on the scene in 2020 with its restaurants set on prime riverfront real estate. You’ll have the best view of the water from one of the deck tables at Oxbow Bar & Grill, where the fare is modern American and the sunsets are spectacular. Further north in Cape Coral, there’s the luxe marina development of Cape Harbour, which includes Fathoms Restaurant & Bar. There, the kitchen team is known for its globally informed dishes—including tuna poke tostadas, an unbeatable banh mi, chimichurri grilled ahi tuna steak and duck leg confit—while its patio and contemporary glassed-in dining room overlook elegant yachts cruising by.

Over the causeway on Sanibel Island, you’ll be hard-pressed to find a more romantic dinner spot than The Mad Hatter, where the whimsical vibe takes a cue from Lewis Carroll and the menu overdelivers on the classics, such as filet mignon, day-boat scallops and lobster tail.