Live music in Sanford, FL

Enjoy a fun evening in Historic Downtown Sanford at the Twilight Artisan Market & Pet Stroll at Henry’s Depot. This monthly event features local artisans and handmade goods, a pet-friendly community stroll with leashed pets welcome, plus live music and a lively downtown atmosphere. Food and drinks are available from the Henry’s Depot food hall, making it a great outing for families and friends.

Set sail aboard the Barbara Lee for a lively river cruise soundtracked by Speed Limit 70. As the ship glides along the St. Johns River and Lake Monroe, the band powers a night of dancing and singalongs to timeless favorites. Operated by St. Johns Rivership Co., this outing departs from the Downtown Sanford Marina. Order food from an a la carte menu, visit the full cash bar for beverages, and take advantage of complimentary parking. Tickets are $25 per adult. Well suited to a date night or a fun evening with friends, with music and waterfront views throughout the journey.

Karaoke hosted by Jenny B features sing-along performances, with pool tables, darts, and poker also available. Drinks are offered, and the staff provides friendly service.

Chosen Legacy Motorcycle Association celebrates its first anniversary at Bravo Supermarkets with DJ Allen providing music, plus food trucks, vendors, trophies, a 50/50, mixed drinks, beer, and more. Everyone is welcome. Admission wristbands are $15 in advance or $20 at the door.

Set out for a relaxing evening cruise along the St. Johns River featuring a three-course dinner. Enjoy thoughtfully prepared dishes as live entertainment sets the mood, and take in the peaceful scenery throughout the voyage.

A dining cruise aboard the Barbara Lee features Songs Through the Years, a live tribute performed by Allan Coffin. The performance ranges across country, rock and roll, blues, heartfelt ballads, and current favorites, with quick transitions that keep the music moving for listeners of many eras. Guests can sing along, sway in their seats, or simply enjoy the passing views as the set flows from one familiar tune to the next. While cruising the St. Johns River and Lake Monroe, a freshly prepared four course meal from the onboard galley is served. Each party has a reserved table in an enclosed, climate controlled dining room with full table service for a relaxed experience. Lunch and dinner cruise options are available. Pricing is 79 dollars per adult for lunch and 98 dollars per adult for dinner. Departures are from the historic downtown Sanford marina.

A blues jam at The Alley in Sanford, FL, hosted by Jim Mahoney. Touted as Central Florida's longest running Tuesday blues jam, it features a full backline with a house PA, drum kit, keyboards, a bass rig, and guitar amplifiers.

This midweek market and hangout takes place at Tuffy's Music Box & Lounge with the Wizards. Attendees can enjoy drinks and snacks while browsing goods from area artists and makers. Activities and performers vary from one hangout to the next, with specifics announced for each edition.

Trivia Nation’s Music Bingo brings a musical twist to classic bingo at Duffy’s Sports Grill Lake Mary. A host keeps the energy high by playing upbeat, popular songs that invite singing and a bit of dancing while the game unfolds. There are $80 in prizes available each week, and it works whether you are playing solo, teaming up with a friend, or making it a family outing.

Karaoke with Jenny B brings lively sing-along nights to Shotski's Food and Drink on Wednesday, Thursday, and Saturday evenings. Take a turn at the mic, then mix in some fun with billiards, poker, or darts, and enjoy wings while you relax. Friendly, upbeat service helps create a welcoming atmosphere for a casual night out.

Hollerbach’s is introducing a summer series that highlights local performers in the main dining room, with Polka reserved for the weekend. This edition features a set by Jon Jacey and is part of a rotating lineup that also includes NDRW, Rhenn Again, Fred Lopacki, The Smoking Jackets, and Iesha Marie. The focus is on an easygoing night of homegrown music in a lively restaurant setting.

An upbeat karaoke gathering featuring singing and dancing, along with pool tables, darts, and poker. Wings and strong, inexpensive drinks are available. The focus is on music, movement, and meeting new people, with a welcoming host who encourages guests to introduce themselves. Many arrive as strangers and leave feeling like family.