So many Florida island restaurants check the right boxes. Waterfront? Check. A surplus of two-tops catering to couples? Check. Plus, as the competition grows, so do the dining experiences being served up, everywhere from Shore on Longboat Key to Little Pearl on Key West.
In our list, we bring you a bit of classic favorites and the new kids on the block so you can try it all.
Thistle Lodge, Sanibel Island
There’s a deliciously warm coziness to Thistle Lodge in Casa Ybel Resort on Sanibel Island. Maybe it’s the thick, polished wood of the bar. Maybe it’s the wood beams and board-and-batten walls. Or the hundreds of twinkle lights on the porch adding their own magic to the evening.
Regardless, this Old Florida setting makes you want to snuggle yours over wine, mussels, black grouper with provencal butter and the rest of the menu of French-meets-Florida fare.
Old Captiva House, Captiva Island
Start with views of the Gulf of Mexico just across Captiva Drive. Then add in the classic charm of the building itself, part of the National Registry of Historic Places. Classic, yes—stuffy, no.
Old Captiva House’s menu, including sushi, duck with an orange-mango-rum glaze and Asian-flavored tuna with wasabi potato, attracts a mixed crowd who appreciate chef Greg Nelson’s leanings toward island flavors—including key limes, guava and watermelon.
Ophelia’s on the Bay, Siesta Key
Call at least a week in advance to enjoy your meal right on the water’s edge—at the string of two-tops Ophelia’s on the Bay refers to as the lower deck. Settle in, then opt for the tender grilled Spanish octopus appetizer or the Burgundy escargots Ophelia, followed by the Gulf grouper with mango Beurre fondue.
Thanks to the dedicated pastry chef, you will want to indulge in dessert, most likely the liquid-center chocolate cake or the chocolate-covered tuile basket filled with Belgian chocolate mousse.
Shore on Longboat Key
Open as of September 2019, this midcentury-modern-hip charmer is the newest location from the team behind the restaurant of the same name on St. Armand’s Circle on Lido Key, Sarasota. Both dish up heightened, fresh takes on southern favorites, such as fried chicken and meatloaf. The vibe at both buzzes with young energy.
Shore’s Longboat Key location is located dockside, making this a happy-hour and dinner destination for the boat set—and all the more happening a spot come sunset to drink in views of pink skies and the yachts floating atop the water reflecting it all.
Espana, Amelia Island
The lush garden patio encourages lingering, perfect for a leisurely meal of tapas where you and yours can nibble and share a wealth of rich flavors, from Portuguese sausage flambéed with brandy to grilled Portobello mushrooms topped with manchego cheese.
Plus, Espana’s wine list offers much to explore, from cavas and proseccos, to tempranillo rose and tawny ports—and of course, homemade sangria.
Latitudes on Sunset Key, Florida Keys
Offering a modern take on Florida style both in the interior design and the menu selections, Latitudes flirts with your senses from the moment you arrive—by boat, no less. Guests reach this date-night must on Sunset Key—so named for its unbeatable location for those hot pink skies—via ferry from Key West, which helps set the mood.
Then get ready to tuck into delectables from carpaccio ahi tuna with caper meringue and basil sauce, to pan roasted rosemary cobia with preserved lemon and tomato vinaigrette.
Little Pearl, Key West
Nestled on Olivia Street a short walk from Duval, Little Pearl sets that just-right date-night ambiance with low lighting and candles, and the restaurant itself is intimate with fewer than 20 tables. On the menu you’ll find seafood dishes with Thai, Korean, Japanese and French flavors. Diver scallops are served with shiitake mushroom bacon.
You’ll also find prawn bibimbap—a take on the Korean classic. The snapper entrée is heightened with a guava beurre blanc. Each dish is an experience, giving you much to talk about and savor.
Pierre’s on Islamorada, Florida Keys
Yes, the two-story plantation house that is Pierre’s is a wedding venue—thanks to its on-the-water location, interior brimming with Balinese wood carvings and a menu of flavors that have received the Zagat nod.
The ever-changing menu showcases the skills and playfulness of executive chef Ishmael Toro, who welcomes international flown-in-daily offerings from Australian lamb to Norwegian salmon, as well as locally caught lobster and black grouper.
Sundowners, Key Largo
Go for an unpretentious spot to watch the sunset Gulf side with a cocktail, stay for the stone crab, ceviche, oysters and other seafood favorites. When in season, the hogfish Fernando is our must-try pick at Sundowners: This local catch is dished up with lump crab meat, tomatoes and scallions and plenty of garlic butter.
The Sandbar Restaurant, Anna Maria Island
Beachy meets updated classic Florida at this Anna Maria favorite right on the water. On the menu, you’ll find seafood plated alongside Southern favorites. One standout entree at The Sandbar is the islander scallops with lemongrass, lime and candied orange; side dishes include cheese grits, hush puppies and made-from-scratch cornbread.
After dinner, enjoy the stars with a walk on the wide, white-sand beach.
