Your Guide to Planning the Month
Pack your sunscreen and calendar—Pensacola in May doesn’t ease into summer, it cannonballs in. From wine tastings to roaring engines and salsa dancing in the streets, there’s a little something for everyone. Here’s your need-to-know guide to this month’s can’t-miss events.
Annual Crawfish Festival
May 2nd-4th
Celebrate 25 years of spicy crawfish, live music, and family fun at Bamboo Willie’s. Bonus: It’s basically a beach bash with claws.
Plant-A-Palooza at Gary’s Brewery & Biergarten
May 3rd
Beer, rare plants, and vegan tacos? You had us at “pale ale brewed just for this.” From 11 AM–5 PM.
Free Yoga at Bayview Park
May 4th
Stretch your weekend with a free morning yoga session at 9:30 AM. BYOM (Bring Your Own Mat—and maybe a towel for your zen sweat).
East Hill Makers Market
May 6th
From 3–7 PM, mingle with makers, shop 60+ local vendors, and snack from food trucks. It’s peak Pensacola charm.
Bands on the Beach
May 6th, 13th, 20th, 27th
Tuesdays hit different when you’re oceanside with a band and a breeze. Live music kicks off at 7 PM at the Gulfside Pavilion. Bring a blanket and some snacks!
Blue Angels Practice at NAS Pensacola
May 6th, 7th, 13th, 14th, 27th, 28th
Watch the Navy’s Blue Angels tear across the sky during their epic practice sessions. Gates open at 9:30 AM, and the show starts at 10:30 AM. May 7, 14, and 28 feature autograph sessions at the Naval Aviation Museum after the flights. Pro tip: arrive early—parking fills up fast and so do the best views.
Succulent Workshop at Coastal Cat Cafe
May 8th
Craft a cat-themed planter while sipping a hot drink and cuddling rescue kitties. Wholesome chaos, in the best way.
Cinemas in the Sand – Moana 2
May 9th
Moana and Maui return to the big screen—beachside! Movie starts at sunset at the Gulfside Pavilion. Free, fun, and family-friendly.
Art & Wine Festival on the Pensacola Beach Boardwalk
May 10th
Peruse local art, sample 50+ wines, and find the perfect last-minute Mother’s Day gift. Tastings begin at 1 PM.
Mother’s Day Brunch at Hilton Pensacola Beach
May 11th
From 9:30 AM–2:30 PM, treat Mom like royalty with live music, mimosas, a photo booth, and coastal vibes. Call ahead—she deserves it.
Full Moon Glow Paddle
May 11th
Kayak under the stars in a glowing, clear-bottom boat. It’s like moonlight therapy—on water.
Hot Rods in Paradise
May 15th-18th
Classic cars, revved engines, and retro conversations take over town. No traffic complaints here.
Gallery Night – “Art in Bloom”
May 16th
Downtown blooms with color and culture from 5–9 PM. Art installations, street performers, and food vendors galore.
Latin Salsa Festival
May 17th
Live music, food vendors, and a vibrant celebration of community and culture. From 12–10 PM, expect nonstop rhythm and spice.
Monster Jam at the Pensacola Bay Center
May 17th-18th
Grave Digger, Sparkle Smash, and El Toro Loco tear it up in dirt-flying, eardrum-rattling glory. You’ll feel it in your bones.
Saenger Theatre’s 100th Birthday Bash
May 24th
Celebrate a century of showtime at the Saenger with music, food trucks, building tours, and free screenings of The Phantom of the Opera.
Weekly & Recurring Events
Brunch at Salt – Every Sunday, 11 AM – 2 PM
Don’t miss brunch at Salt inside Hilton Pensacola Beach. Try the Shrimp and Grits—Cajun grilled shrimp, smoked gouda grits, and andouille sausage.
Palafox Market – Every Saturday, 9 AM – 2 PM
Shop fresh produce, artisan goods, and handmade crafts at this award-winning market in Downtown Pensacola.
Red Fish Blue Fish Coin Flip Happy Hour – Monday to Friday, 2 PM – 5 PM
Try your luck at happy hour! Call the coin flip right, and your drink is free.
Pensacola doesn’t do boring, and May proves it. So, bring your beach bag, your appetite, and your dancing shoes—this month’s schedule is packed and ready for action.
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