FRI 8/14–SUN 8/23
Stage Crafters: Ken Ludwig's “Moriarty”
Fort Walton Beach Civic Auditorium
A Sherlock Holmes comedy takes the stage.
/Sat 7:30 PM · Sun 2 PM · two weekends (8/14-16, 8/21-23)
Date Night
The grown-up half of the list. The app will plan the whole evening for you.
Date Night
72 nights out · the app chains dinner, the main event and a night cap with drive times
Tuesdays + Thursdays thru FRI 10/2
Wine, Cheese & Sunset Dolphin Cruise: SOL y LUNA
SOL y LUNA, Baytowne Marina, Sandestin · Miramar Beach
SOLARIS's little sister offers a 1.5-hour sunset cruise with two wine pours and a cheese pairing each, dolphins likely.
6:30 PM · 1.5 hr
21+THU 8/20
Bubbly Baytowne: Free Champagne Sip & Shop (21+)
Village of Baytowne Wharf, Sandestin · Miramar Beach
A free evening stroll winds through the village with complimentary bubbly pours at the merchants, a browse-and-taste date that costs nothing unless something in a shop window wins.
5:00-7:00 PM · also 9/17
21+Thu thru FRI 10/16
Live Music: Manci's Antique Club
Manci's Antique Club · Daphne
This Daphne institution has walls of Jim Beam decanters and live local bands Thursday through Sunday.
6:30 · Fri-Sat 7:30 · Sun 6:00 PM
21+Nightly thru FRI 10/16
Karaoke & DJ Nights: FUBAR Pizza Bar
FUBAR Pizza Bar · Fort Walton Beach
Late-night karaoke runs five nights a week (Sun, Tue, Wed, Fri, Sat) plus a DJ on Monday and Thursday, 9 PM to 1 AM every night, with pizza till close.
9 PM-1 AM
21+Wed-Sat thru FRI 10/16
Karaoke Block: The Block
The Block · Fort Walton Beach
The Sports & Karaoke room at The Block runs Wednesday through Saturday, opening at 6 (8 on Thursday) and going late.
From 6 PM (Thu 8 PM)
Every night thru SAT 10/31
Karaoke at Lili Marlene's: every night
Seville Quarter, Lili Marlene's · Pensacola
Karaoke runs seven nights a week in the aviators' room, not just on the weekend, which makes it the answer to a Tuesday you did not plan.
8:00-11:00 PM
18+Thursdays thru THU 10/29
College Night: Seville Quarter (18+)
Seville Quarter, Phineas Phogg's · Pensacola
The Gulf Coast's oldest Thursday tradition, in the club room of an 1871 warehouse block.
From 8:00 PM
FRI 8/21–SUN 8/30
Dracula: A Comedy of Terrors
Pensacola Little Theatre
A laugh-out-loud stage spoof of Dracula takes the stage.
/Sat 7:30 PM · Sun 2:30 PM · two weekends
21+Every weekend thru FRI 10/16
Weekend Live Music: Sandshaker Lounge
Sandshaker Lounge · Pensacola Beach
The Shaker, birthplace of the Bushwacker, has live music every weekend and never a cover.
Evenings
21+Tue thru FRI 10/16
Live Music: Paradise Bar & Grill
Paradise Bar & Grill · Pensacola Beach
Beachside live music plays most nights on Pensacola Beach, with rotating local acts starting at 5:30 (Sundays 2:30).
/Fri/Sat 5:30 PM · Sun 2:30 PM
Fridays thru FRI 10/30
Flip My Quarter: Friday happy hour
Seville Quarter, Apple Annie's · Pensacola
Call the coin flip and the drink is free; miss it and you pay.
6:00-8:00 PM
Fridays thru FRI 10/30
Rosie O'Grady's Dueling Piano Show
Seville Quarter, Rosie O'Grady's · Pensacola
Two pianos take requests shouted from the floor, and the room sings back.
8:00-11:00 PM
FRI 8/21
Comedy on the Boulevard: the last summer show
Emerald Coast Theatre Company · Suite 200
This is the final night of ECTC's summer stand-up run, upstairs at Grand Boulevard.
7:00 PM
FRI 8/21
DIY Accessories Craft Night: Destin Library
Destin Library
Materials out, instructions on the table, make something you can wear.
6:00 PM
FRI 8/21
Goo Goo Dolls: The Wharf Amphitheater
The Wharf Amphitheater · Orange Beach
This open-air amphitheatre on the Intracoastal has ten thousand seats and a band whose whole catalogue is a singalong.
8:00 PM
SAT 8/22
Vince Gill: 50 Years From Home Tour
Saenger Theatre · Pensacola
Country royalty plays in the historic Saenger, gospel-friendly, completely clean, and about as elegant as a date night gets in this town.
Evening (time TBA)
SAT 8/22
Kellen Erskine: CLEAN Stand-Up (Mattie Kelly)
Mattie Kelly Arts Center, Sprint Theater · Niceville
A Dry Bar-style comic takes the stage, billed by the venue as all-ages clean, the rare comedy night that needs zero content asterisks.
7:00-8:30 PM
SAT 8/22
Goo Goo Dolls: Wharf Amphitheater
The Wharf Amphitheater, Orange Beach
"Iris" plays under the open sky, 90s/2000s nostalgia built for a 32-year-old couple.
Evening (time TBA)
Tuesdays and Saturdays thru SAT 10/31
The Brandon Styles Variety Show
Brandon Styles Theater at OWA · Foley
Celebrity impressions, comedy, and magic play a purpose-built theatre at OWA, twice a week.
7:00 PM
18+SAT 8/22
Island Fights 57: The Forgotten Show
Pensacola Bay Center
Pensacola's long-running professional MMA card takes place in the arena.
7:00 PM
Sundays thru SUN 10/25
Sunday Brunch with John Wheeler: Seville Quarter
Seville Quarter, Apple Annie's · Pensacola
Brunch runs in the courtyard room while John Wheeler plays through it.
11:00 AM-2:00 PM
Mondays thru MON 10/26
Bar Bingo: Seville Quarter
Seville Quarter, Apple Annie's · Pensacola
A free-to-play bingo night runs in Apple Annie's courtyard room, inside the 1871 warehouse block that has been Pensacola's night-out address for fifty years.
8:00-10:00 PM
Mondays thru MON 10/26
Monday Night Blues: Lili Marlene's
Seville Quarter, Lili Marlene's · Pensacola
Live blues plays in the World War I aviators' room, which the venue keeps smoke-free, the one room in the complex where you can hear the band and still hear each other.
7:00-9:00 PM
21+Tuesdays thru FRI 10/16
Team Trivia Night: Coastal County Brewing
Coastal County Brewing Co. · Pensacola
Grab a team and a local craft pour.
6:30 PM
Tuesdays thru TUE 8/25
Wine + Song at NEAT: Alys Beach
NEAT Tasting Room & Bottle Shop · Alys Beach
Four wines and a live guitarist fill two hours in Alys Beach's tasting room, at a fixed price, a fixed length, and a drive that is genuinely part of the evening.
5:00-7:00 PM · thru 8/25
18+Wednesdays thru WED 10/14
Ballroom Dance Night: Let's Dance Pensacola
Sanders Beach-Corinne Jones Resource Center · Pensacola
Weekly cha-cha, waltz, and swing lessons run from championship instructors through the city rec department.
6:30-8:30 PM
18+Wednesdays thru FRI 10/16
Ladies Night: Flora-Bama
Flora-Bama Lounge · Perdido Key
The legendary state-line roadhouse runs Ladies Night every Wednesday 6-9 with free admission, then live music across its stages the rest of the night.
6:00-9:00 PM
21+Wednesdays thru FRI 10/16
Karaoke Night: AJ's Oyster Shanty
AJ's Oyster Shanty · Fort Walton Beach
Early-evening karaoke runs on Okaloosa Island every Wednesday 6-9, with oysters, a Gulf view, and a mic.
6:00-9:00 PM
WED 8/26
Jack Johnson: The Wharf Amphitheater
The Wharf Amphitheater · Orange Beach
The most on-brand booking the Gulf Coast will get all summer, outdoors on the Intracoastal.
7:30 PM
18+Wednesdays thru WED 10/28
Noche Tropical: Latin night (18+)
Seville Quarter, Phineas Phogg's · Pensacola
A midweek Latin dance night fills the club room, featuring salsa, bachata and reggaeton on a floor that actually dances.
From 7:00 PM
THU 8/27
Jack Johnson: Wharf Amphitheater
The Wharf Amphitheater, Orange Beach
Mellow acoustic surf-rock plays at sunset, about as low-key and clean as a big-venue date gets.
Evening (time TBA)
FRI 8/28
Light of the Moon Climb: Pensacola Lighthouse
Pensacola Lighthouse & Maritime Museum, NAS Pensacola
Climb 177 steps, then watch sunset over the Gulf on one side and the full moon rising on the other.
4:30-8:30 PM · sunset + moonrise
SAT 8/29
Jason Aldean: Wharf Amphitheater
The Wharf Amphitheater, Orange Beach
Aldean headlines the Wharf's C Spire series about 40 minutes west, a clean country date night with openers Chase Matthew, Mackenzie Carpenter, and Dee Jay Silver.
Time TBA
SAT 8/29
Western Murder Mystery Dinner Theatre
Heritage Hall at Seville Quarter · Pensacola
This frontier-saloon whodunit downtown includes dinner, a cast working the room, and clues you actually chase.
Doors 6:00 PM · Show 7:00 PM (runs to ~10 PM)
FRI 9/4–SAT 9/5
Leanne Morgan: Clean Comedy (date night)
Pensacola Bay Center
Clean stand-up comedy plays two nights at the Bay Center, a date-night pick for the adults, not a kids' show.
7:00 PM
AdultsSUN 9/6
Flux Pavilion: Labor Day weekend at Laguna's
Laguna's Beach Bar + Grill · Pensacola Beach
A dubstep headliner plays the boardwalk for Labor Day weekend, the biggest touring name the beach bars book all year.
Labor Day weekend
THU 9/10–SUN 9/27
Come From Away: Emerald Coast Theatre Co
Emerald Coast Theatre Company · Miramar Beach
The Tony-winning true story follows a town that fed and housed 7,000 stranded 9/11 passengers.
Thu-Sat 7 PM · Wed + Sun 2 PM
THU 9/10–SUN 9/20
Come From Away: Chickasaw Civic Theatre
Chickasaw Civic Theatre
The heartfelt true story of Gander, Newfoundland taking in stranded 9/11 passengers gets staged by a community theatre about an hour west.
Eves + matinees
FRI 9/11
Girls Gone Bible: Revival Tour
Saenger Theatre, Pensacola
The Girls Gone Bible revival tour comes to the Saenger, a faith-centered worship night downtown.
Evening
SAT 9/12
Ty Myers: The Legal Tour
The Wharf Amphitheater, Orange Beach
Rising country and soul singer-songwriter Ty Myers plays under the stars at The Wharf, a warm-night date about 50 minutes west.
Evening
THU 9/17
Josh Turner: This Country Music Thing
Saenger Theatre · Pensacola
Deep-voiced, gospel-rooted country plays the Saenger, one of the cleaner big country nights in town.
7:30 PM
18+FRI 9/18–SUN 9/20
Gulf Coast Summer Fest (Jazz Edition)
Community Maritime Park, Pensacola
A downtown-waterfront jazz-and-R&B festival fills the weekend, and the rules say 18-and-over only.
20/2026 · gates 1 PM, music 2 PM
SAT 9/19
White Tie Rock Ensemble: 80s Rock Night
Pensacola Bay Center
The local symphonic-rock spectacle covers 80s arena hits.
Evening
SAT 9/19
Pensacola Opera Jukebox Gala: Dinner + Table-Side Opera
Hilton Pensacola Beach
Cocktail hour, a four-course dinner, and 30+ table-side opera performances chosen by the room's bids make this the dressiest date on the fall calendar.
6:00 PM · formal
SAT 9/19
Use Your Illusion: Guns N' Roses Experience
OWA Theater · Foley
This GnR tribute plays OWA, a loud classic-rock date about an hour west.
Evening
SAT 9/19
Totally 80s Murder Mystery Dinner Theatre
Heritage Hall at Seville Quarter · Pensacola
Neon, big hair, and a body in the room set the scene.
Doors 6:00 PM · Show 7:00 PM
SAT 9/26
Gabriel “Fluffy” Iglesias: The 1976 Tour
Pensacola Bay Center
The biggest-room comedy of the fall is Fluffy, who runs mostly clean (PG-13, mild language, no filth).
Evening
SAT 9/26
Light of the Moon Climb: September Full Moon
Pensacola Lighthouse & Maritime Museum, NAS Pensacola
The September edition of the sunset-and-moonrise climb brings the first properly cool evening of the series, and it falls on a Saturday.
4:30-8:30 PM
SAT 9/26
Gabriel Iglesias: The 1976 Tour
Pensacola Bay Center
"Fluffy" brings The 1976 Tour downtown.
Time TBA
THU 10/1–SUN 10/11
Pensacola Beach Songwriters Festival (cherry-pick sets)
22+ venues, Pensacola Beach + downtown
Ten days of acoustic storyteller rounds run, mostly free, a build-your-own date.
Venue-by-venue schedule
FRI 10/2–SUN 10/11
Ballet Pensacola: Frankenstein (two weekends)
Ballet Pensacola, The Center · FL 32502
A gothic, atmospheric Frankenstein ballet spans two October weekends, a moody, elegant date.
Times TBA
SAT 10/3
Pensacola Symphony: Opening Night
Saenger Theatre · Pensacola
The dress-up date of the fall opens the 2026-27 season in the Saenger.
7:30 PM
SAT 10/3
“Weird Al” Yankovic: Wharf Amphitheater
The Wharf Amphitheater, Orange Beach
The cleanest big show of the fall offers pure absurd fun and October air.
8:00 PM
SUN 10/4
Roman Street
Saenger Theatre · Pensacola
This local instrumental duo plays Latin and smooth-jazz guitar, easy and romantic.
7:30 PM
THU 10/8–SUN 10/11
Taste of the Beach: Pensacola Beach
Casino Beach / beach venues · Pensacola Beach
A beach food festival fills the weekend.
Sat daytime = the family window
THU 10/8
Postmodern Jukebox: The Future Is Vintage
Saenger Theatre · Pensacola
Modern pop hits are reworked as 1920s-50s jazz and swing, a stylish, clean, dress-up date night.
8:00 PM
18+FRI 10/9
Daniel Tosh: My First Farewell Tour
Saenger Theatre, Pensacola
Tosh's "My First Farewell Tour" plays the Saenger downtown.
7:00 PM
SAT 10/10–SUN 10/11
Mobile Symphony: Spectacular! (Pictures at an Exhibition)
Mobile Saenger Theatre
The Mobile Symphony season opener features Mussorgsky's Pictures at an Exhibition.
Oct 10 (7:30 PM) + Oct 11 (5:00 PM), 2026
THU 10/15–SUN 10/25
The 39 Steps: Hitchcock Farce (ECTC)
Emerald Coast Theatre Company · Miramar Beach
Four actors play 150 roles in a full-tilt Hitchcock spoof that is clean, fast, and laugh-out-loud.
Thu-Sat 7 PM · Wed + Sun 2 PM
FRI 10/16
Choral Society of Pensacola: “Voices of the Sea and Sky”
Sanders Beach-Corinne Jones Resource Center · Pensacola
The Choral Society's season opener is sea-and-sky themed and held in the waterfront resource center.
7:30 PM
FRI 10/16
Nirvanna: A Tribute to Nirvana (Vinyl)
Vinyl Music Hall · Pensacola
The cleanest pick on Vinyl's fall calendar brings a faithful 90s grunge tribute with Crawling opening.
8:00 PM · doors 7:00
FRI 10/16–SUN 11/1
Blithe Spirit: Theatre 98
Theatre 98, Fairhope
Noël Coward's classic ghost-comedy plays at Fairhope's intimate community playhouse, a witty, dressed-up date about 50 minutes west.
Eves + matinees
THU 10/22
CeCe Winans: Come Worship! Pensacola
Pensacola Bay Center
A worship night brings the most-awarded female gospel artist ever, the strongest faith-aligned date on the fall calendar.
Evening
21+FRI 10/23
Taste of Gulf Breeze (21+)
Gulf Breeze Community Center
The Chamber's annual tasting night features more than 50 local restaurants, food trucks, and bakeries with unlimited samples, Golden Spatula voting, and a live DJ.
6-9 PM · VIP entry 5 PM
FRI 10/23–SAT 10/24
Rocky Homicide Murder Mystery Dinner Theatre
Heritage Hall at Seville Quarter · Pensacola
This boxing-gym whodunit downtown is the longest run of the series, four nights across two weekends.
Doors 6:00 PM · Show 7:00 PM · also 10/29-10/30
18+SAT 10/31
Saosin: Vinyl Music Hall
Vinyl Music Hall, Pensacola
This Halloween-night reunion show downtown is loud and nostalgic.
Doors 6, show 7 PM
TUE 11/10
Hawthorne Heights: Vinyl Music Hall
Vinyl Music Hall, Pensacola
Mid-2000s emo plays downtown on a Tuesday, a nostalgic, low-key date night.
Doors 6, show 7 PM
WED 11/11
Fortunate Youth: Vinyl Music Hall
Vinyl Music Hall, Pensacola
Laid-back West-Coast reggae plays downtown on Veterans Day, an easy, mellow date night.
Doors 6, show 7 PM
THU 11/12–SUN 11/22
Noises Off!: Chickasaw Civic Theatre
Chickasaw Civic Theatre
Michael Frayn's door-slamming backstage farce, one of the funniest plays ever written, plays at Chickasaw's community playhouse about an hour west.
Eves + matinees
THU 11/12
Tab Benoit with Jesse Dayton
OWA Theater · Foley
Louisiana swamp-blues plays at OWA, a soulful, clean, grown-up night.
Evening
WED 11/18
Whose Live Anyway?
Saenger Theatre · Pensacola
The 'Whose Line' improv cast performs live, fast, clean, audience-driven comedy.
7:30 PM