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Live Music
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May 2026
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Concert
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East Naples
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Barbara B. Mann Performing Arts Hall
Celebration Park
Compass Hotel by Margaritaville Naples
Giuseppe and the Lion
Hertz Arena
Mercato Naples
Rooftop at Riverside
Sugar Shack Downtown
The Hampton Social
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Mon
18
May
Live Music
Bryce Ivie
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Mon
18
May
Live Music
Bryce Ivie
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Mon
18
May
Live Music
Island Entertainment Karaoke
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Mon
18
May
Live Music
Island Entertainment Karaoke
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Tue
19
May
Live Music
Battle of the Bands
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Tue
19
May
Live Music
Battle of the Bands
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Tue
19
May
Food & Drink
Manhattan Connection
6:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Tue
19
May
Food & Drink
Manhattan Connection
6:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Tue
19
May
Live Music
CONO & DANGER
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Tue
19
May
Live Music
CONO & DANGER
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Wed
20
May
Food & Drink
Matt Stone Live
5:00 PM – 8:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Wed
20
May
Food & Drink
Matt Stone Live
5:00 PM – 8:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Wed
20
May
Live Music
Hunter McDaniel
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Wed
20
May
Live Music
Hunter McDaniel
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Wed
20
May
Live Music
Matty Jollie
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Wed
20
May
Live Music
Matty Jollie
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Wed
20
May
Live Music
Wooftop Fest
6:00 PM – 8:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Wed
20
May
Live Music
Wooftop Fest
6:00 PM – 8:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Thu
21
May
Live Music
Eric Whitener
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Thu
21
May
Live Music
Eric Whitener
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Thu
21
May
Food & Drink
Sweet Fleet A Tribute to Fleetwood Mac
7:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Thu
21
May
Food & Drink
Sweet Fleet A Tribute to Fleetwood Mac
7:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Thu
21
May
Live Music
Live Music Thursdays
6:00 PM – 9:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Thu
21
May
Live Music
Live Music Thursdays
6:00 PM – 9:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Thu
21
May
Live Music
Edison Schetter
5:00 PM – 7:00 PM
·
The Hampton Social
North Naples
The Hampton Social
Thu
21
May
Live Music
Edison Schetter
5:00 PM – 7:00 PM
·
The Hampton Social
North Naples
The Hampton Social
Thu
21
May
Live Music
Ross Brown
6:00 PM – 8:00 PM
·
Rooftop at Riverside
Multiple Dates
Bonita Springs
Rooftop at Riverside
Thu
21
May
Live Music
Ross Brown
6:00 PM – 8:00 PM
·
Rooftop at Riverside
Multiple Dates
Bonita Springs
Rooftop at Riverside
Thu
21
May
Live Music
Andy Moreillon
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Thu
21
May
Live Music
Andy Moreillon
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Fri
22
May
Live Music
From $48
Josh Gates Live! An Evening of Legends, Mysteries and Tales of Adventure
8:00 PM – 10:00 PM
·
Barbara B. Mann Performing Arts Hall
Fort Myers
Barbara B. Mann Performing Arts Hall
Fri
22
May
From $48
Live Music
Josh Gates Live! An Evening of Legends, Mysteries and Tales of Adventure
8:00 PM – 10:00 PM
·
Barbara B. Mann Performing Arts Hall
Fort Myers
Barbara B. Mann Performing Arts Hall
Fri
22
May
Live Music
Juice
7:00 PM – 10:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Fri
22
May
Live Music
Juice
7:00 PM – 10:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Fri
22
May
Live Music
Majesty of Rock
7:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Fri
22
May
Live Music
Majesty of Rock
7:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Fri
22
May
Live Music
Live Music Fridays
6:00 PM – 9:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Fri
22
May
Live Music
Live Music Fridays
6:00 PM – 9:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Fri
22
May
Live Music
Danielle Brittany
5:00 PM – 7:00 PM
·
The Hampton Social
North Naples
The Hampton Social
Fri
22
May
Live Music
Danielle Brittany
5:00 PM – 7:00 PM
·
The Hampton Social
North Naples
The Hampton Social
Fri
22
May
Live Music
Even Keel Band
6:00 PM – 9:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Fri
22
May
Live Music
Even Keel Band
6:00 PM – 9:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Fri
22
May
Live Music
Austin James
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Fri
22
May
Live Music
Austin James
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Fri
22
May
Live Music
DJ Honeybee (Copy)
9:00 PM – 11:59 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Fri
22
May
Live Music
DJ Honeybee (Copy)
9:00 PM – 11:59 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Fri
22
May
Live Music
DJ Honeybee
9:00 PM – 11:59 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Fri
22
May
Live Music
DJ Honeybee
9:00 PM – 11:59 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Sat
23
May
Live Music
Matty Jollie
1:00 PM – 4:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sat
23
May
Live Music
Matty Jollie
1:00 PM – 4:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sat
23
May
Live Music
TI Jentgens
7:00 PM – 10:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sat
23
May
Live Music
TI Jentgens
7:00 PM – 10:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sat
23
May
Live Music
Ben Allen Band
7:00 PM – 9:30 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Sat
23
May
Live Music
Ben Allen Band
7:00 PM – 9:30 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Sat
23
May
Live Music
Complimentary
Sounds on Strada
6:00 PM – 9:00 PM
·
Piazza
Multiple Dates
North Naples
Mercato Naples
Sat
23
May
Complimentary
Live Music
Sounds on Strada
6:00 PM – 9:00 PM
·
Piazza
Multiple Dates
North Naples
Mercato Naples
Sat
23
May
Live Music
Live Music Saturdays
5:00 PM – 8:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Sat
23
May
Live Music
Live Music Saturdays
5:00 PM – 8:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Sat
23
May
Live Music
Jenny Vē
11:30 AM – 1:30 PM
·
The Hampton Social
North Naples
The Hampton Social
Sat
23
May
Live Music
Jenny Vē
11:30 AM – 1:30 PM
·
The Hampton Social
North Naples
The Hampton Social
Sat
23
May
Live Music
Matty Jollie
1:00 PM – 4:00 PM
·
Celebration Park
East Naples
Celebration Park
Sat
23
May
Live Music
Matty Jollie
1:00 PM – 4:00 PM
·
Celebration Park
East Naples
Celebration Park
Sat
23
May
Live Music
Hunter McDaniel
1:00 PM – 4:00 PM
·
Celebration Park
East Naples
Celebration Park
Sat
23
May
Live Music
Hunter McDaniel
1:00 PM – 4:00 PM
·
Celebration Park
East Naples
Celebration Park
Sat
23
May
Live Music
Dino's trio band
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Sat
23
May
Live Music
Dino's trio band
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Sat
23
May
Live Music
Phenominal Animal
6:00 PM – 9:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Sat
23
May
Live Music
Phenominal Animal
6:00 PM – 9:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Sun
24
May
Live Music
The Yacht Rockers
1:00 PM – 4:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sun
24
May
Live Music
The Yacht Rockers
1:00 PM – 4:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sun
24
May
Live Music
Michael Dutra Strictly Sinatra
5:00 PM – 8:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Sun
24
May
Live Music
Michael Dutra Strictly Sinatra
5:00 PM – 8:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Sun
24
May
Live Music
Sprout
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sun
24
May
Live Music
Sprout
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Sun
24
May
Live Music
Live Entertainment Sunday
2:00 PM – 5:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Sun
24
May
Live Music
Live Entertainment Sunday
2:00 PM – 5:00 PM
·
Compass Hotel by Margaritaville Naples
Multiple Dates
Midtown Naples
Compass Hotel by Margaritaville Naples
Sun
24
May
Live Music
Claire Liparulo
11:30 AM – 1:30 PM
·
The Hampton Social
North Naples
The Hampton Social
Sun
24
May
Live Music
Claire Liparulo
11:30 AM – 1:30 PM
·
The Hampton Social
North Naples
The Hampton Social
Sun
24
May
Live Music
Sunday Yoga
12:00 PM – 1:00 PM
·
Rooftop at Riverside
Multiple Dates
Bonita Springs
Rooftop at Riverside
Sun
24
May
Live Music
Sunday Yoga
12:00 PM – 1:00 PM
·
Rooftop at Riverside
Multiple Dates
Bonita Springs
Rooftop at Riverside
Sun
24
May
Live Music
Joel Fry Band
5:00 PM – 8:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Sun
24
May
Live Music
Joel Fry Band
5:00 PM – 8:00 PM
·
Rooftop at Riverside
Bonita Springs
Rooftop at Riverside
Mon
25
May
Live Music
Driftstone Duo
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Mon
25
May
Live Music
Driftstone Duo
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Mon
25
May
Live Music
Island Entertainment Karaoke
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Mon
25
May
Live Music
Island Entertainment Karaoke
6:00 PM – 9:00 PM
·
Celebration Park
East Naples
Celebration Park
Tue
26
May
Live Music
Manhattan Connection
6:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Tue
26
May
Live Music
Manhattan Connection
6:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Tue
26
May
Live Music
Battle of the Bands
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Tue
26
May
Live Music
Battle of the Bands
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Wed
27
May
Concert
"Weird Al" Yankovic: Bigger & Weirder 2026 Tour
7:30 PM – 10:30 PM
·
Hertz Arena
Estero
Hertz Arena
Wed
27
May
Concert
"Weird Al" Yankovic: Bigger & Weirder 2026 Tour
7:30 PM – 10:30 PM
·
Hertz Arena
Estero
Hertz Arena
Wed
27
May
Live Music
Lasagna Day
4:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Wed
27
May
Live Music
Lasagna Day
4:00 PM – 9:00 PM
·
Giuseppe and the Lion, 1585 Pine Ridge Road, Naples, FL, FL, 34109, United States
Midtown Naples
Giuseppe and the Lion
Wed
27
May
Live Music
Sweendog
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
Wed
27
May
Live Music
Sweendog
6:00 PM – 9:00 PM
·
Sugar Shack Downtown
Bonita Springs
Sugar Shack Downtown
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