Live Entertainment, Dancing & Nightlife – 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. At the south bridge on Stickney Point, there’s also an open air second floor Daiquiri Deck location.


Cross a bridge to discover Sarasota’s varied clusters of entertainment. Each club, bar or restaurant offers its own particular style and is generally within walking distance to other venues.

From the North Bridge of Siesta Key

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 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 Grill features a low key Cheer’s like atmosphere and plenty of friendly local conversation.


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

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

The Blue Rooster serves up good Southern food with great blues bands belting out a tune after 8:00 pm.

Located at 1991 Main, the Old School Bar and 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 beers.  Check their events calendar for movies, music and more.

Head to McCurdy’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 and O’Leary’s come to mind. 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.

The Westin Hotel Rooftop Bar is the perfect spot for those panoramic views.

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 music and Jimmy Buffett hits. Sailing several times a day around Sarasota Bay it offers great views of waterfront homes and spectacular sunsets. Be sure to bring that camera.

Into sunsets with a more intimate feel?

Key Sailing’s 41’ sailboat heads out from Marina Jack’s offering a relaxing sunset adventure you’ll never forget. Just bring your favorite libation.

Capture a sunset and tranquil views at Jack Dusty’s expansive outdoor patio lounge.  Go to the Ritz Carlton at 1111 Ritz Carlton Drive.

St. Armand’s Circle

Plan to spend at least one evening at 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 pianist, great drinks and deserts.

If you’re looking for boat drinks, Cha Cha Coconuts has ’em and live music too. This is a great place to have a drink and work on your Hemmingway style.

A cheeseburger in Paradise may be good – but a dozen oysters in Paradise is much better! 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 acts like Roadblock, Rising Tide, Swamp Root Funk Band, Local Celebrity Band and Left Hand Side.


Head to the Haye Loft at Euphemia Haye Restaurant. There’s a great line-up of jazz with full bar, comfortable seating and Dessert Room offering imported coffees, teas, appetizers, salads, sandwiches and personal pizzas. Entertainment rotates nightly.

From the South Bridge of Siesta Key

In the Gulf Gate Area

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.

Looking for something a little different from traditional bars? The Thirsty Turtle and Detention are always serving reasonably priced strong drinks to anyone over 21 with a good attitude.

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.

Like a lot of the taverns in the area, Hurricane Mike’s is crowded with blue-collar drinkers on weeknights while weekends bring a young contingency.