The Weekend Lineup: May 15-17

**The [Orange Beach](/directory/orange-beach/) Billfish Classic kicks off Friday -- big boats, blue marlin, and free admission at Marlin Circle for one of the Gulf Coast's best fishing tournaments. The Asian/Pacific American Festival runs Saturday and Sunday in Pensacola with food, performances, and cultural showcases. Weather is about as good as it gets for mid-May: sunny Friday with a high of 81, mostly sunny Saturday at 82, and Sunday holds at 82 with only an 11% chance of rain -- light winds all three days.**

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## Friday

### [Orange Beach Billfish Classic](/events/orange-beach-billfish-classic-2026-05-15-2/) -- [Portside at the Wharf](/directory/portside-at-the-wharf/), Free, 12:00 AM CT

The Orange Beach Billfish Classic is a two-day tournament -- Friday and Saturday -- and the first major stop in the Gulf Coast Triple Crown Series. This one is family-run and fishing-focused, with blue marlin as the headline species alongside tuna, wahoo, and mahi. Weigh-ins happen at Marlin Circle and are free to watch, which makes it one of the better spectator sports on the water this weekend -- standing next to a 700-pound marlin on the scale is something else.

### [Tee Off Turned Up Live Music Series](/events/tee-off-turned-up-live-music-series-2026-05-15/) -- [The Stage at Portside](/directory/portside-at-the-wharf/), 12:00 AM CT

The Tee Off Turned Up series runs Thursday through Sunday all summer at The Stage at Portside, rotating through local favorites and high-energy bands week to week. It's a good setup -- covered outdoor stage, easy access to food and drinks, works equally well as a pre-dinner hang or a full night out.

### [Live Music -- Strickly Rivers](/events/live-music-strickly-rivers-2026-05-15-82ca427c/) -- [Cosmo's Restaurant & Bar](/directory/cosmos-restaurant-bar/), 2:00 PM & 4:00 PM CT

Roger Strick and Flo Rivers play under the covered patio at Cosmo's Friday afternoon. It's a relaxed way to spend a few hours, and the timing lines up perfectly with happy hour.

### [Gallery Night: Festa Italiana](/events/gallery-night-festa-italiana-2026-05-15/) -- [Gallery Night Pensacola](/directory/gallery-night-pensacola/), Free, 5:00 PM CT

Pensacola's monthly Gallery Night is doing an Italian-themed edition this Friday. It's the third-Friday tradition -- galleries open late, streets fill up, and there's usually food and music mixed in. Palafox is under construction but Gallery Night is still running; they've adapted the route, so worth checking the event page for the current layout before you head downtown.

### [Sunset Cruise from the AWF Delta and Bay Conservation Center at Five Rivers](/events/sunset-cruise-from-the-awf-delta-and-bay-conservation-center-at-five-rivers-2026-05-16/) -- [Bartram Landing at AWF Delta and Bay Conservation Center at Five Rivers](/directory/bartram-landing-at-awf-delta-and-bay-conservation-center-at-five-rivers/), $22/adults, 7:00 PM & 8:00 PM CT

A short boat cruise out of Bartram Landing at Five Rivers, timed to catch the sunset over the lower Delta. The plan is to be back early enough to grab a seafood dinner on the Causeway after -- which is a pretty ideal Friday night on the water. Two departure times available: 7 PM and 8 PM.

### [Gator Cruise](/events/gator-cruise-2026-05-16/) -- [Bartram Landing at AWF Delta and Bay Conservation Center at Five Rivers](/directory/bartram-landing-at-awf-delta-and-bay-conservation-center-at-five-rivers/), 7:00 PM & 8:00 PM CT

Also out of Five Rivers Friday evening -- this one heads into the secluded reaches of the lower Delta after dark, looking for alligators and other nocturnal wildlife. Two departure times at 7 PM and 8 PM. If you have kids who want to see a gator in the wild, this is a more structured way to make that happen.

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## Saturday

### [Orange Beach Billfish Classic](/events/orange-beach-billfish-classic-2026-05-15-2/) -- [Portside at the Wharf](/directory/portside-at-the-wharf/), Free, 12:00 AM CT

Day two of the Billfish Classic. The weigh-ins are where the action is -- Marlin Circle is the place to be when the boats come in with their catch. Free to spectate, and the crowd energy around a good weigh-in is hard to beat.

### [Ballin' on Belrose 2026](/events/ballin-on-belrose-2026-2026-05-16/) -- [Olde Towne Daphne](/directory/olde-towne-daphne/), 7:00 AM CT

An early morning community basketball event in [Olde Towne Daphne](/directory/olde-towne-daphne/) with a nonprofit fundraising angle -- the East Shore Art Center has a team registered and is working toward a big goal this year. Good excuse to get out to Daphne before the heat kicks in.

### [Asian/Pacific American Festival](/events/asianpacific-american-festival-2026-05-16/) -- 234 West Oakfield Road Pensacola, Florida 32503, 9:00 AM CT

A two-day cultural festival running Saturday and Sunday in Pensacola, featuring food, performances, art, and community showcases from across Asian and Pacific Islander communities. It's a family-friendly event and one of the more distinctive things happening in the region this weekend. Saturday starts at 9 AM -- worth making the drive up if you're in the area.

### [Home Sweet Home Gulf Coast Block Party](/events/home-sweet-home-gulf-coast-block-party-2026-05-16/) -- 351 W Cedar St, Pensacola, FL 32502, 12:00 AM CT

A block party in Pensacola spotlighting local real estate pros, home service providers, makers, and artists. Think neighborhood market energy -- a good excuse to browse local businesses and meet some of the people behind them.

## Sunday

### [Asian/Pacific American Festival](/events/asianpacific-american-festival-2026-05-16/) -- 234 West Oakfield Road Pensacola, Florida 32503, 9:00 AM CT

Day two of the festival at the same location in Pensacola. If you missed Saturday, Sunday gives you another shot. Mostly sunny with an 11% rain chance -- nothing that should slow things down.

### [2026 Pensacola Beach Art and Wine Festival](/events/2026-pensacola-beach-art-and-wine-festival-2026-05-09/) -- [Pensacola Beach Boardwalk](/directory/400-quietwater-beach-rd-pensacola-beach-florida-32561/), 12:00 PM CT

The festival doubles in size this year, taking over the [Pensacola Beach Boardwalk](/directory/pensacola-beach-boardwalk/) and Gulfside Pavilion with 60+ tents and live music on two stages. The $75 Grand Tasting from 2--5 PM gets you unlimited pours at 25 wine, seltzer, and spirits tents -- 100+ selections, a commemorative glass, and light bites from local restaurants. Walk the boardwalk to browse the 20+ artist booths even if the tasting ticket isn't your thing.

### [Live Music -- Lisa Christian](/events/live-music-lisa-christian-2026-05-17-b00d49d0/) -- [Cosmo's Restaurant & Bar](/directory/cosmos-restaurant-bar/), 2:00 PM & 4:00 PM CT

Lisa Christian plays the covered patio at Cosmo's Sunday afternoon, running alongside happy hour. A low-key way to close out the weekend.

### [Mahjong Lessons -- Beginner](/events/mahjong-lessons-beginner-2026-05-17/) -- 1625 W Garden St Pensacola, Florida 32502, 2:00 PM CT

A beginner-level American Mahjong class in Pensacola Sunday afternoon. If you've been curious about the game but haven't had anyone to show you the ropes, this is a structured start -- solo attendees welcome.

### [Smokey Otis Band](/events/smokey-otis-band-2026-05-17/) -- [Flora-Bama Lounge](/directory/flora-bama-lounge/), 5:30 PM CT

The band's own description gets it right: classic rock, outlaw country, motown, soul, with a splash of reggae and disco poured over rhythm and blues. Smokey Otis fronts a four-piece on Flora-Bama's Dome Stage from 5:30 to 9:30 -- one of the more reliable live-music slots on a Sunday close to the water.

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## The Full Lineup

Find all 36+ events this weekend at [gulfshoreslineup.com/events/](/events/).

*Got a tip or event we should know about? Email [email protected]*