Italian
Recommended
15 South by Napule
St. Armands Circle · $$$
Italian trattoria with handmade pasta, wood-fired Neapolitan pizza, an upstairs lounge and live entertainment.
Insider tip: Choose downstairs for a traditional meal or the upstairs lounge for music, cocktails and small plates.
Casual Dining
Recommended
Cottonmouth Southern Soul Food
Bradenton
Southern soul food and live music venue now operating at Flamingo Bay Brewing Co. in Bradenton.
Dolphin & Eco Tours
Recommended
LeBarge Tropical Cruises
Downtown Sarasota · $$
A distinctive floating-island cruise boat offering sunset, sightseeing, dolphin and manatee, live-music, and private charter experiences on Sarasota Bay.
Insider tip: Arrive at least 30 minutes before departure; reservations open three weeks in advance.
Waterfront Dining
Recommended
Linger Lodge Restaurant & Bar
Bradenton · $$
Quirky Old Florida restaurant on the Braden River serving Southern favorites, seafood, smoked meats, alligator and frog legs, with screened waterfront decks and live entertainment.
Insider tip: Request a screened-deck table for Braden River views; the taxidermy-filled interior is part of the unusual Old Florida experience.
Casual Dining
Recommended
Mattison's City Grille
Downtown Sarasota · $$$
Open-air downtown restaurant serving New American food, cocktails and frequent live entertainment at Lemon Avenue and Main Street.
Insider tip: Check the music schedule and expect a livelier atmosphere on event nights.
McCurdy's Comedy Theatre
Downtown Sarasota
Established comedy club presenting touring and regional stand-up performers.
Casual Dining
Recommended
Stottlemyer's Smokehouse
East Sarasota · $$
Open-air East Sarasota smokehouse, live-music venue and Old Florida tiki bar specializing in barbecue.
Insider tip: Check the music schedule and weather; the open-air setting is a major part of the experience.
Casual Dining
Recommended
Tommy Bahama Restaurant & Bar - St. Armands
St. Armands Circle · $$$
Island-inspired restaurant and bar serving seafood, salads, tropical cocktails and weekend brunch in a polished resort setting.
Insider tip: Reservations are especially helpful during season; check the entertainment schedule for live music.
941-388-2888 · tommybahama.com/restaurants-and-marlin-bars/locations/sarasota
Casual Dining
Recommended
Whitney's
Longboat Key · $$
Beachside all-day restaurant and bar in a restored 1950s service station with coastal food, cocktails, weekend brunch and live music.
Waterfront Dining
Recommended
Woody's River Roo Pub & Grill
Bradenton
Old Florida waterfront pub and grill in Ellenton overlooking the Manatee River with seafood, burgers, tiki bars and live music.
Sushi & Asian
Bar Hana
Downtown Sarasota · $$$
Tiki-inspired downtown bar and restaurant pairing tropical cocktails with pan-Asian small plates from the KOJO culinary team.
Insider tip: Treat it as a cocktails-and-small-plates destination rather than a conventional full dinner.
Casual Dining
Blase Martini Bar
Siesta Key · $$
Funky Siesta Key Village martini bar with food, cocktails and nightly live music.
Insider tip: Go in the evening for the full live-music and martini-bar atmosphere.
Casual Dining
Daiquiri Deck - Siesta Key Village
Siesta Key · $$
Flagship Siesta Key Village Daiquiri Deck serving frozen drinks, casual food and seafood in an open-air setting.
Casual Dining
Daiquiri Deck - St. Armands Circle
St. Armands Circle · $$
Open-air casual restaurant and bar known for frozen daiquiris, seafood, pub fare and a lively atmosphere.
Insider tip: Popular for drinks and a lively atmosphere; families may prefer earlier hours.
Latin & Peruvian
El Melvin Cocina Mexicana
Downtown Sarasota · $$$
Energetic Mexican restaurant and tequila bar serving tacos, shareable dishes and cocktails on Main Street.
Insider tip: The atmosphere becomes louder later in the evening; families may prefer an earlier meal.
Casual Dining
Gilligan's Island Bar & Grill
Siesta Key · $$
Lively Siesta Key Village bar and grill with outdoor seating, tropical drinks and entertainment.
Casual Dining
Guppy's Good Times
Longboat Key · $$
Casual Philly-themed sports bar and grill with cheesesteaks, burgers, wings, tacos, live music and multiple televisions.
Waterfront Dining
Marina Jack Dining
Downtown Sarasota · $$$
Downtown bayfront dining destination with an upstairs dining room, casual patio options, marina views, and live entertainment.
Insider tip: Choose the dining room for a more polished meal or the patio for a casual waterfront experience.
Casual Dining
Mattison's City Grille - Bradenton Riverwalk
Bradenton · $$
Open-air Bradenton Riverwalk restaurant serving casual American fare with frequent live music.
Insider tip: Pair it with a Riverwalk stroll and check the live-music calendar before you go.
Casual Dining
Midway Lounge at Cirque St. Armands Beachside
Lido Key · $$$
Stylish lobby lounge serving cocktails, light bites and Ringside menu selections in Cirque St. Armands.
Insider tip: Check the resort entertainment calendar for live music and busier evening periods.
941-413-5992 · opalcollection.com/cirque-st-armands/eat-and-drink
Waterfront Dining
Nokomo's Sunset Hut
Osprey / Nokomis · $$
Casual Dona Bay waterfront restaurant and tiki bar with Caribbean-influenced food, nightly music and boat access.
Insider tip: This is primarily an outdoor waterfront experience; plan around the weather.
Waterfront Dining
Pelican Alley
Osprey / Nokomis · $$
Long-running Nokomis waterfront restaurant on the Intracoastal serving seafood, daily specials and patio dining.
Insider tip: Friday music nights can fill up, so call ahead when live entertainment is part of the plan.
Waterfront Dining
Pop's Sunset Grill
Osprey / Nokomis · $$
Large casual waterfront landmark on the Intracoastal in Nokomis with tiki dining, boat access and live music.
Insider tip: Boat access and abundant outdoor seating make this a particularly good stop on a nice-weather day.
Seafood
Siesta Key Oyster Bar
Siesta Key · $$
Popular Siesta Key Village oyster bar serving seafood, drinks and a lively island atmosphere.
Waterfront Dining
Spearfish Grille
Siesta Key · $$
Small marina-side Siesta Key restaurant serving fresh local fish, island dishes and nightly live music.
Fine Dining
The Cottage Restaurant
Siesta Key · $$
Eclectic Siesta Key Village restaurant blending local seafood with globally inspired dishes and patio dining.
Latin & Peruvian
The Hub Baja Grill
Siesta Key · $$
Colorful Siesta Key Village restaurant serving Baja-style Mexican fare, cocktails and live entertainment.
Bahi Hut Tiki Bar
Sarasota · $$
Historic Sarasota tiki bar operating since 1954, known for its legendary Mai Tai, vintage Polynesian atmosphere, happy hour and recurring live entertainment.
Insider tip: Go Monday through Thursday between 1 and 6 PM for happy hour. Friday and Saturday evenings feature live music.
Hours, prices, and details change. Call ahead to confirm before you go. Know a place we should add? Use the form below.