Live music in Winter Springs, FL

Set sail for a music-filled dining cruise featuring Allan Coffin, who leads a tribute to decades of favorites. Expect an upbeat blend of country, rock and roll, blues, heartfelt ballads, and contemporary hits, with smooth transitions that keep the music flowing for a wide range of tastes. Take in views along the St. Johns River and Lake Monroe while enjoying a freshly prepared four course meal from the onboard galley. A reserved table in the enclosed, climate controlled dining room and full table service create a comfortable, unhurried setting. Lunch and dinner sailings are offered, with pricing at $79 per adult for lunch and $98 per adult for dinner. It is a river cruise that pairs live music, dining, and scenic waterways for a memorable time on the water.

Live Local Thursdays at Hollerbach's introduces a new summer series that moves polka to the weekend while Thursdays highlight local talent in the main dining area. This edition features The Smoking Jackets as part of the rotating lineup of hometown performers.

Hosted by Jenny B at Shotski's Food and Drink, this karaoke and dance night blends singing with a welcoming social vibe. The venue offers pool tables, darts, and poker, along with wings and stiff, low priced drinks. Guests can take the mic, dance, and meet new people, arriving not knowing anyone and heading out with new friends. Guests can introduce themselves to Jenny B.

Gillian Carter, Dial Drive, Suck Brick Kid, and Effit perform live at Tuffy’s. Tickets are $15 pre-sale and $20 the day of the show.

Settle in for a relaxing evening on the water with a three course dinner served as the boat cruises the St. Johns River. Thoughtfully prepared dishes are complemented by live performances and plenty of time to soak in the river’s serene scenery.

Nicko McBrain's Titanium Tart returns to The Barn in Sanford with a tribute to Iron Maiden. The performance includes classic songs and stories shared by Nicko McBrain. Maximum Friction and Medal Militia are slated as opening acts. A limited presale for general admission and VIP standing in front of the stage will be available for a limited time, with additional details and ticket links to be announced. Booking is handled by Lazer Focused Talent Agency.

This concert celebrates 30 years of the Persona video game series with music from Persona and Shin Megami Tensei, along with other RPG favorites. The lineup features Lacey Johnson, Bi Score, Trash Burger, and Mintea. It is presented by Ongaku Overdrive, with sponsorship from Materia Music and Cybertron Video Games.

Ella & The Bossa Beat comes back to Blue Bamboo with a concert celebrating AMARE, the group’s new album on Schema Records in Milan in 2026. Composed entirely of the band’s original songs and featuring a collaboration with TOCO, the release includes the singles "Amanhecer" with 400K+ streams, "Areia" with 280K+, and "Amare" with 280K+. The performance unfolds in an easygoing bossa lounge setting that blends smooth grooves with upbeat moments that encourage singing and dancing. The set also features beloved Brazilian classics reimagined with the band’s own arrangements. This international father-daughter ensemble features Ella Blu on vocals and piano, Magrus Borges on drums and percussion, André Lafaete on bass and guitar, and Alain Bradette on saxophone and flute. Ella is a multilingual vocalist and pianist who performs in Portuguese, English, and Italian, and she collaborates closely with her father on composing, lyric writing, and producing. Her style draws on classic jazz, enriched with soul, bossa nova, and Brazilian jazz. In 2020, she received the Focus Brazil Award for Best Female Singer in Orlando.

Trade the usual dinner-and-drinks routine for a candlelit evening inspired by the Harlem Renaissance, where live music, laughter, connection, and vintage glamour set the tone. New York City duo Acute Inflections guides the night with a distinctive sound that nods to the timeless grace of Billie Holiday and the soulful spirit of Erykah Badu. They have performed for more than 50,000 guests at sold-out shows across the U.S. and abroad, have been featured on HBO and Amazon, and have earned over a thousand five-star reviews. Attire can range from Gatsby-style elegance to your own personal look. Complimentary snacks will be available throughout the show. Set at Venue on Lake Lily, a waterfront location in downtown Maitland with lake views, this intimate single-evening experience offers a setting that feels special. Ticket purchases help support the Renaissance Youth Center, a South Bronx charity that empowers inner-city youth through music education, after-school programs, and tutoring.

An Orlando event featuring Profanatica and Cloak alongside other performers. The night brings multiple acts together on one stage, with these two artists at the forefront.

Karaoke night brings lively sing-along vibes to Brooklyn South Bar, with Shining Starz hosting an evening of crowd-pleasing performances. Share the mic with friends and belt out favorite tunes in a relaxed, welcoming setting. Between songs, enjoy a full-service menu that includes snacks and appetizers, house specialties, hand-tossed pizzas, burgers, handcrafted sandwiches, fresh salads, and more.

Central Florida's longest running blues jam takes place on Tuesday. A complete backline is provided, including a house PA, drum kit, keyboards, a bass rig, and guitar amplifiers. The jam is hosted by Jim Mahoney.

An open mic and jam that invites solo performers, duos, and full bands. Drink specials at $4, $5, and $6 are available throughout the night. A backline is provided with a house PA, drums, keys, a bass rig, and guitar amps, so performers can plug in and play.