The 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.
Friday
Orange Beach Billfish Classic -- 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 -- The Stage at Portside, 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 -- Cosmo's 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 -- 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 -- 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 -- 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.
Saturday
Orange Beach Billfish Classic -- 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 -- Olde Towne Daphne, 7:00 AM CT
An early morning community basketball event in 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 -- 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 -- 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 -- 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 -- Pensacola Beach Boardwalk, 12:00 PM CT
The festival doubles in size this year, taking over the 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 -- Cosmo's 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 -- 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 -- 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.
The Full Lineup
Find all 36+ events this weekend at gulfshoreslineup.com/events/.
Got a tip or event we should know about? Email [email protected]