A wooden footbridge leading to the beach

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After Hours On The Islands

It’s after 6 p.m. on Longboat Key. The sun is about to set and dinner plans are calling. It’s a gorgeous evening all around, and there’s absolutely no reason not to extend it well into the night. The area’s evenings are generally balmy, breezy and buzzing with entertainment both indoors and out. Whether you find yourself on Longboat Key, Siesta Key, St. Armands or in downtown Sarasota, a range of nightlife options are available. Here are six of our favorites.

The Classic Piano Bar: The Haye Loft

Euphemia Haye’s lofty quarters upstairs reveal a cozy, elegant bar and lounge, but it’s the fact that this spot offers live music every single night of the week that really makes it special. The gracious maple bar is stocked with top-shelf liquor, but there are romantic booths overlooking the treetops outside, too. Wherever you settle in, you can sample from the abbreviated menu, simply enjoy the craft cocktails or come ready for the Dessert Bar: the pies are famous here!

The Crowd Pleaser: Mattison’s City Grille Downtown Sarasota

Locals know there’s only one place to go to catch all the action downtown and hear great music. Mattison’s patio is expansive and sits right on the corner of Lemon Avenue and Main Street, the perfect place for some people-watching. This is a great meet-up spot for happy hour (or after hours), and there’s almost always live music being performed from a surprisingly substantial stage. This patio is under cover, too, so even if it’s raining you can still enjoy the social scene and dance the night away on the packed floor.

The Modern Florida Backyard Spot: The Cottage

Tucked away on a Siesta Key side street just a tad removed from the village hub bub sits this modest-looking restaurant. Climb a short flight of stairs into what seems a typical island pub inside, but go out back and it’s another scene altogether. The back patio transports you to a subtropical paradise (try to claim the tiki hut, with its circular, pillow-studded booth), lush with trees and plants, clusters of tables and all kinds of Key-themed decor. The best part? The musicians who routinely take the small corner stage, playing everything from Flamenco to gypsy jazz. And while you might assume the food would be as unassuming as the exterior, think again. Korean Short Rib, Peruvian Ceviche and Guava Slaw are just a few items on the fresh, Asian-inspired menu.

The Place For Latin Lovers: 15 South

St. Armands is a whole night unto itself, but if you’re in the mood for Latin music and dancing, this is your destination. Yes, you can enjoy 15 South’s scrumptious Northern Italian fare from the restaurant downstairs, but don’t miss the nightclub one floor up. Both jazz and Latin bands play here regularly, to an enthusiastic dance floor and a horseshoe-shaped bar. Step outside for a breather and have a drink on the ample balcony, which offers beautiful views of The Circle.

The Chic City Spot: Jack Dusty

The Ritz-Carlton Sarasota’s signature restaurant is exactly what you’d expect from the upscale hotel: refined, contemporary and serving innovative, seafood-centric fare. But this nautical-themed restaurant is even more known for its lounge, which extends out onto a beautiful patio that overlooks the Ritz pool, gardens and harbor. This is the perfect spot for happy hour or an after-dinner cocktail, and what cocktails they are. Ranging from Sippers to Gulpers, these concoctions are mixed to perfection (try The Siren) and unlike anything you’ve had before. Sink down into the chairs and couches on the patio where the gas fire pits and swaying palms set the mood.

The Laugh Factory: McCurdy’s Comedy Theatre and Humor Institute

McCurdy’s has been going strong since 1988 and has welcomed the biggest names in comedy—think Poundstone, Schumer, Rock and Nealon—to its stage. After a location move and renovation, the beloved comedy club finds itself strategically situated in the heart of Downtown Sarasota, putting it within walking distance of restaurants and bars (as well as three parking garages, but there’s valet also). Have a light bite and a drink at McCurdy’s Green Room East End before claiming your table among the cabaret-style seating in the spacious main room. Shows run about two hours in this family-run club.