Cocktails with a View
These 10 bars and restaurants have something for everyone, whether you like it tiki, crafty, urban, beachy, fancy, or dressed-down. One thing they all have in common: an incredible view. Happy hour could become your new favorite form of sightseeing!
Casual
1 Seafood Shack
The indoor scene at this Old Florida gem is just as interesting as the outdoor one, with antique crab traps, lobster pots, ethereal glass floats, and other boating equipment suspended from the ceiling. The decor pays tribute to Seafood Shack’s historic fishing village home of Cortez, while the 270° view of Anna Maria Sound gives a sample of the vistas you might glimpse from one of the parasails waiting at the marina. Order up a glass of Shack Rum Punch if you need a juicy boost of courage— maybe make it a pitcher.
2 The Old Salty Dog: City Island
Tank tops, f lip-f lops, and Fido are all welcome at The Old Salty Dog! For a stellar sight of Sarasota Bay, perch at a high-top by the rail at the City Island location and get ready for some serious drinks. These attitude adjustments come at you big, boozy, and laden with enough fresh fruit garnish to cure the scurviest pirate. They’re great for washing down bites of Old Salty’s infamous battered-and-fried hot dog!
Craft
3 Jack Dusty
This upscale port-in-a-storm at the Ritz-Carlton warmed Sarasota to the concept of the hotel bar that welcomes you whether or not your ride home is the elevator. Its ultra-craft-cocktail menu features plenty of fresh juices and bubbles, but herbal, vegetable, spice, and smoke elements deepen many cups’ complexity. Ice is an ingredient here, not just a chiller, sometimes frozen with fruit, flower petals, and aromatics inside for an eye-popping (not to mention tasty) effect.
4 The Waterfront Restaurant
Amid frond-topped tiki bars and beachfront lounges, one might not expect to stumble upon an island speakeasy. You’ll find one at the Waterfront Restaurant on the northeast edge of Anna Maria Island. Modeled on the hippest craft bars of Manhattan, its recipes put Floridian twists on classic cocktails, each one a spectacle that’s almost— almost—too lovely to drink. Focused on 100 % fresh ingredients, spiced rum is the closest thing to flavored liquor you’ll see on the shelf here.
Elegant
5 Dry Dock Waterfront Grill
Tucked away on the east side of Longboat Key, the Dry Dock Waterfront Grill’s manicured patio gazes away to the mainland. Should you miss most of sunset’s riotous spectacle behind you, consolation comes as night deepens in the shimmer and twinkle of Sarasota’s lights across the bay. This ideal after-golf destination practically insists you sip on a dry martini or an old-fashioned after coming off the links.
6 Pier 22
There’s something extra-romantic about a riverfront, which makes PIER 22’s deck overlooking the Manatee River a great first stop on date night. The water flows like scintillating conversation; each sip from your happy-hour drink emboldens you to take a journey, chart a course whose destination you can’t yet see—but each searching glance over the rim of your glass lets you glimpse a little more of what’s around the bend.
Tiki
7 Oleary’s Tiki Bar & Grill
Oleary’s is no-frills, but who needs extra frills when you’ve got toes scrunched in sand while a local troubadour croons about living on sponge cake? Sometimes it just doesn’t get better than a cold drink in a plastic cup or the crunch of a Bloody Mary–soaked pickle. Oleary’s offers a precious opportunity to get eyelevel with Sarasota Bay close to downtown, admire a flotilla of serenely bobbing boats, and sail away on daydreams for a while.
8 Sharky’s on the Pier
Best place in Venice to catch a case of brain freeze? The tiki deck at Sharky’s on the Pier.
Sharky’s is Venice’s only beachfront eatery, and its “Famous Frozens” deliver heavenly refreshment after soaking up some rays or landing a ketch a few steps away on the Venice Fishing Pier. Sample all five Frozens—a classic pina colada … a luscious rum runner … an electric blue margarita … an indulgent mudslide … or the “soon-to-be-famous” Mango Bango, a true tropical smash—then choose wisely, because two’s the limit with these babies!
Rooftop
9 The Roof Bar and Eats at Westin Sarasota
When you visit the Westin Sarasota’s rooftop bar, you and your companions may not have much to say to one another for the first five minutes. Words are easily snatched away by the awe-inspiring panorama, Sarasota Bay on one side, the city stretching away on the other—the best of both worlds in an eyeful that’s interrupted only if you blink. Eventually you’ll come to your senses and remember how to order one of The Roof Bar’s sunshine-inspired tropical drinks. Consume it at complete leisure in these ultra-heady surroundings.
10 Perspective at Art Ovation Hotel
The Westin’s stunning bar debut whetted Sarasota’s appetite for more rooftop options, and the boutique Art Ovation Hotel answered soon after. Where the Westin’s view from 19 floors up is dazzling, the sights from Perspective are utterly charming, the city below rendered toy-sized rather than bug-sized. Sarasota’s skyline cradles this bar, lending it intimacy though it’s open to the air. A compelling cocktail menu reads like a list of magic potions best enjoyed while sunset casts a spell of its own.
