1. At Flounders Restaurant and Tiki Bar, the tiki bar, crackling fire pits, live music and water view set the mood. With pub grub fare like “Wing It,” “Bite It,” “Shuck It,” and “Build It,” the menu makes it easy. Just grab a Technicolor libation and get social. Or come for breakfast (Saturdays and Sundays) and indulge in one of the popular breakfast cocktails, like the Tiki Mary, a spicy hot powerhouse created with jalapeño-infused Ketel One vodka and garnished with blue cheese-stuffed olives, pepperoncini, jalapeño bacon and a Cajun rim. The ideal eye-opener. 1975 Beach Road, Englewood, (941) 460-8280.
2. Beach Road Wine Bar and Bistro is called Englewood’s jewel by the sea for many good reasons. A selection of more than 60 exceptional vintages, the culinary delights of a chef-driven menu, the jaw-dropping views of Lemon Bay—and the spirit of camaraderie that enlivens on the outside patio. How to add to that? On many evenings, there’s a soundtrack of live music by regional musicians. 1350 Beach Road, Englewood, (941) 474-9500.
3 The inventive menu at Farlow’s on the Water marries Caribbean classics with down-home Southern cuisine. This fusion reflects the heritage of Keith Farlow, who grew up in St. Croix, and his wife, Laurie, who glories in the tastes of Dixie. Ask for a table on the comfortable outdoor patio and dig into some corn pudding or sizzling St. Croix seafood pie. You can also grab a table overlooking Ainger Creek, and watch Florida’s natural beauty unfold before your eyes. 2080 S. McCall Road, Englewood, (941) 474-5343.
4 Keep your eyes peeled for gators, otters, eagles and other wild critters at Myakka River Oyster Bar Seafood Restaurant, which sits smack-dab on the Myakka River. Going on 23 years, JoAnn and Mike Stegenga have kept folks well-fed with daily specials, fresh seafood, pasta and sandwiches. Although most fish is regionally sourced, the walleye special is an exception, created from the recipe of Mike’s mother. “Lots of people from Minnesota come here just for the walleye,” says JoAnn. With just six outside tables, come early to claim your perch. 121 Playmore Drive, Venice, (941) 423-9616.
5 People-watching is an art. Begin your life studies at one of Ristorante San Marco’s sidewalk tables. This charming Italian trattoria offers front row seats on fashionable Venice Avenue. Don a white suit and your jet-black Wayfarers, order a bottle of Camigliano Brunello di Montalcino and pretend you’re the star of Fellini’s La Dolce Vita. Just watch out for paparazzi. 305B W. Venice Ave., (941) 254-6565.
6 Envision yourself sipping a chilled Lillet on the terrace of a Monte Carlo brasserie overlooking the Mediterranean. Lost your passport? The Crow’s Nest affords you similar bliss closer to home. Kick back with a chilled fumé blanc from Sonoma and watch the pleasure boats sailing down Venice Inlet. If you’re with your special someone, order a dozen oysters from the raw bar and embark on a romantic interlude as the sun makes its sensational descent. 1968 Tarpon Center Drive, Venice, (941) 484-9551.
7 The outside deck at Fins at Sharky’s boasts picture-postcard views of the Gulf of Mexico and Venice Fishing Pier, a tranquil ambiance, an award-winning menu and wine selection and sexy craft cocktails like the Cucumber Caroline with Pimms and rosemary-infused syrup. With patio fans and a retractable screen shielding wind and direct sunlight, you’ve got it made in the shade. There are only 18 outside tables, so best to reserve ahead of time. 1600 Harbor Drive S., Venice, (941) 999-3467.
8 Old Florida is alive and well at the Casey Key Fish House, a bustling waterside joint in Osprey famed for its laid-back ambiance, solid seafood offerings, gorgeous views, and tiki bar with live music on the weekends. Grab a table on the deck and dig into such signature dishes as Chef Willie Tia’s raved-about bouillabaisse, mussels slathered in the house-made marinara sauce, and the conch fritters. If you’re feeling adventurous, rent a jet ski, paddleboard or kayak right on the dock. Or wander down to the beachside tiki bar and meet some new friends. 801 Blackburn Point Road, Osprey, (941) 966-1901.