St. Armand’s Circle

Catch a bite to eat and head to 15 South Ristorante Enoteca featuring live music at the upstairs nightclub called “Straight-up” on Avenue of the Presidents.

The Crab & Fin enjoys sidewalk seating with a pianist belting a tune while patrons enjoy great drinks and deserts.

If you’re looking for boat drinks, Cha Cha Coconuts has ’em and live music too.

Catch some sun then chill with a frozen daiquiri at the Daiquiri Deck. Wednesdays is “80s for the Ladies”, with dancing and live music. Fridays and late-night Saturdays feature bands like Roadblock, Rising Tide, Swamp Root Funk Band, Local Celebrity Band and Left Hand Side.

Longboat Key

The Haye Loft at Euphemia Haye Restaurant features a great line-up of jazz with full bar, comfortable seating and Dessert Room.

Downtown Sarasota

Pulsating nightly, Mattison’s City Grill draws a huge crowd at its covered open-air bar and eatery offering Blues, Jazz, Rock, Pop and Swing on the corner of Lemon and Main.

Directly across on Main, is the Gator Club offering exceptional live music beginning around 9:00pm. The upstairs bar boasts 125 single malt scotches, pool tables and comfy couches for relaxing.

The Blue Rooster serves up good Southern food with great Blues Bands belting a tune after 8:00 pm.

Sarasota Sky Bar & Club at 1927 Ringling Blvd. keeps the dance floor packed and the booze flowing with bands playing Reggae and music of the ’60’s.

Located at 1991 Main, the Old School Bar & Grill is more than a sports bar as it features live music Friday and Saturday nights.

The Mandeville Beer Garden at 428 N. Lemon Ave., offers indoor/outdoor seating, plus burgers, homemade sausages and craft beer.  Check their events calendar for movies, music and more.

Head to McCudy’s Comedy Club for a fun time and plenty of laughter.  Be sure to join the crowd for drinks and party bites in the Green Room before and after the show.  McCurdy’s is located downtown at 1923 Ringling Blvd.

Sarasota’s Bayfront

Marina Jacks features a huge covered patio with band and area for dancing. You can even slip inside and sing along at the piano bar.

O’Leary’s Tiki Bar and sandy beach is at the opposite end of Centennial Park attracting a crowd at sunset with live Reggae and beach music.

Also at Centennial Park is Le Barge… a giant houseboat with bar, dance floor and cocktail tables on the top deck. Entertainment is usually a solo guitar player/singer performing island style and Jimmy Buffett tunes. Sailing several times a day around Sarasota Bay it offers great views of waterfront homes and spectacular sunsets. Be sure to bring that camera.

Hillview Street and Osprey Avenue

The Five O’Clock Club is a laidback neighborhood bar attracting everything from cowboy boots to gauzy blouses… and all drawn to the best of “Blues”, rock and more. Daily performances start around 5:30pm followed by another band requiring a cover around 8:00pm.

New York Times Review… “The Five O’Clock Club is a rocking dive bar that’s been showcasing live music since 1955. On any given night, there might be reggae or an eccentric AC/DC tribute band”.

Music is not the only attraction of this neighborhood for there are several comfortable spots for libations, gawking and a bit of gab.

Libby’s Café and Veronica’s are havens for singles and young professionals with curbside dining and plenty of people watching. Pacific Rim is another “in-crowd” spot with excellent drinks, sushi and patio seating while Knick’s Grill features a low key Cheer’s like atmosphere and plenty of friendly local conversation.

Gulf Gate Area (near Stickney Point and Clark Roads)

Gulf Gate is a hodgepodge of restaurants, businesses and bars located on Gulf Gate, Mall Drive, Superior and Gateway Avenues. Gulf Gate revels in its down-to-earth, unique establishments and events.

The Sarasota Brewing Company is the only microbrewery in the county. This family-friendly, rustic-themed establishment provides plenty of sports and award- winning beer.

Since opening its doors, Pastimes, a beige music and sports pub on the west side of Superior Avenue, has become known for bringing all types of music to Gulf Gate… from rockabilly to classic rock to electronica.

Siesta Key

After dark, Siesta Key takes on new life as Ocean Boulevard draws a youthful crowd to the rocking sounds of The Beach Club where live music and crazy contests keep patrons coming back for more. Gilligan’s turns it down a notch with a cool tiki bar in the back and live entertainment every night while the Daiquiri Deck mixes it up with more contests and sporting events.

The Cottage is also in Siesta Village offering live Latin music and exceptional Peruvian dining.