Longboat Key

Most nightly entertainment occurs off island yet, there’s one location mixing it up every single night and that’s the “Haye Loft” at Euphemia Haye Restaurant.  They feature a great line-up of live music with full bar, light menu and a fabulous Dessert Room .

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.

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.

Selva Grill, (Main Street) offers jazz on Fridays & Saturdays in the lounge.

The Blue Rooster (Fourth Street) features music nightly. Closed Mondays.

Sarasota’s Bayfront

Marina Jacks boasts 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.

Sarasota’s downtown Westin Hotel features a Rooftop Bar with expansive views of the bayfront.

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 OspreyAvenue

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.

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

Veronica’s and Libby’s Café is a haven 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 Tavern has a low key Cheer’s like atmosphere and plenty of friendly local conversation.

Other good establishments include Bijou Cafe, Selva Grill, Caragiulo’s, Barnacle Bills, Café Epicure and Patrick’s.

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.