🌴 What's Happening in Naples: May 25 - May 31

This is the first full week after Memorial Day, and the town settles into its summer rhythm. Old Town Saloon owns the weekend with Gator's Mayday Bash on Friday and a Saturday meet-and-greet, the East Tamiami lounge runs a late Latin night, and the 4805 Tamiami patio has live music four nights straight. The Saturday farmers market is back on Third Street South, FC Naples plays Saturday, and the Vanderbilt Beach Road extension is close enough to opening that you can almost drive it. Bigger picture: hurricane season opens June 1, sea turtles are nesting on the barrier islands, and it is a good week to sign up for Alert Collier before the first storm name lands. Here is what is worth getting off the couch for.

We recommend confirming with event hosts for complete details and current schedules.

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🍽️ Food & Drink Events

🍺 Brews, Bubbles, and Business
📅 Date: Thursday, May 28, 2026
⏰ Time: 5:00 PM
📍 Location: 5111 Tamiami Trail N, Naples, FL
🥂 Details: 33 interested, 7 going. The biggest midweek mixer of the week. Beer, bubbles, and a young-professional crowd that actually talks shop. Easy first stop before dinner.

🍷 "Classics from France & Spain" Wine Tasting Event
📅 Date: Tuesday, May 26, 2026
⏰ Time: 7:00 PM
📍 Location: Naples Wine Bar
🍇 Details: A guided pour through French and Spanish classics with the bar's resident pourer doing the storytelling. Smaller, smarter crowd than the average tasting.

🥬 Third Street South Farmers Market
📅 Date: Saturday, May 30, 2026
⏰ Time: 7:30 AM
📍 Location: Third Street South Farmer's Market, Naples
🍓 Details: The Saturday classic. Best place in town for the bakery box, the bouquet, and the cold-pressed juice you forget about until Tuesday.

🥞 Sunday Beachside Brunch at HB's
📅 Date: Sunday, May 31, 2026
⏰ Time: 11:00 AM
📍 Location: 801 Gulf Shore Boulevard North, Naples, FL
🌊 Details: HB's on the Gulf rolls out beachside brunch on the sand at the Naples Beach Club. Toes in the sand, Bloody Mary in hand, the water right there. Get there early on a holiday weekend.

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🎵 Music & Entertainment

🍺 Gator's Mayday Bash
📅 Date: Friday, May 29, 2026
⏰ Time: 7:00 PM
📍 Location: Old Town Saloon Naples
🎉 Details: 37 interested. The biggest bar night of the week and the unofficial start of summer at Old Town. Live music, drink specials, and a crowd that turns up early and stays late.

🤝 Meet & Greet at Old Town Saloon
📅 Date: Saturday, May 30, 2026
⏰ Time: 4:00 PM
📍 Location: Old Town Saloon Naples
🍻 Details: 32 interested, 8 going. Saturday afternoon hang at the same room that ran Friday's bash. Easy walk-in, regulars trading stools, the kind of spot where the bartender remembers your order.

🔥 KAZZABE Featuring Las Catrachas & DJ Arell
📅 Date: Friday, May 29, 2026
⏰ Time: 9:00 PM
📍 Location: 2634 Tamiami Trail E, Naples, FL
💃 Details: Late Latin night on East Tamiami with a live act and DJ Arell holding the floor. Dress comfortable, come ready to dance, the crowd takes the floor seriously.

🪗 Tropical Latin Night 2026: Practice and Enjoy
📅 Date: Friday, May 29, 2026
⏰ Time: 7:30 PM
📍 Location: 4367 Tamiami Trail N, Naples, FL
🕺 Details: Half social-dance practice, half party. Salsa and bachata with an instructor to get you moving early, then open floor once the lesson wraps. Beginners welcome.

🎶 Katie O at Celebration Park
📅 Date: Sunday, May 31, 2026
⏰ Time: 6:00 PM
📍 Location: Celebration Park Naples
🌮 Details: Sunday evening set at the food-truck park on Bayshore. Grab a taco and a craft beer, post up at a picnic table, and let Katie O close out the weekend.

🎸 Live Music Saturdays: Head Above Water
📅 Date: Saturday, May 30, 2026
⏰ Time: 5:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎵 Details: The band the regulars show up for, on the patio that runs music almost every night. Saturday fills up fast in summer, so get there before six.

🎤 Live Music with Joe Marino
📅 Date: Sunday, May 31, 2026
⏰ Time: 2:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎶 Details: Sunday afternoon set from a steady local. The kind of show you walk into for one drink and stay for three.

🎧 Live Music: Taylor Tones
📅 Date: Thursday, May 28, 2026
⏰ Time: 6:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎸 Details: Thursday night on the same Tamiami patio. Easy acoustic-leaning set, good way to start the long weekend a day early.

📖 Open Mic Night at Food & Thought
📅 Date: Friday, May 29, 2026
⏰ Time: 6:00 PM
📍 Location: 2132 Tamiami Trail North, Naples, FL
☕ Details: Friday open mic at the organic cafe. Singer-songwriter heavy, family-friendly, espresso flowing into the second half of the night.

🎲 Twisted Bingo: Music Bingo Naples
📅 Date: Monday, May 25, 2026
⏰ Time: 7:00 PM
📍 Location: Dylan's Drafthouse, Naples
🍻 Details: Memorial Day Monday music bingo at Dylan's. Name the song, mark the card, win the round. Free to play, drinks flowing, no team required.

🎯 Monday Trivia on Marco Island
📅 Date: Monday, May 25, 2026
⏰ Time: 7:00 PM
📍 Location: Paddy Murphy's Irish Pub, Marco Island
🍀 Details: Monday night quiz on Marco. Free to play, drink specials run all night, the bartenders know the regulars by name.

🍕 Monday Night Trivia in Estero
📅 Date: Monday, May 25, 2026
⏰ Time: 7:00 PM
📍 Location: Naples Flatbread Kitchen & Bar, Estero
🧠 Details: The Estero version of the Monday quiz. Same friendly format, woodfire pizza, easy walk-in even with a team of two.

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🎭 Arts & Theater

🎻 Artis Naples Chamber Concert
📅 Date: Friday, May 29, 2026
⏰ Time: 2:00 PM
📍 Location: 5200 Crayton Road, Naples, FL
🎼 Details: Afternoon chamber program at the Crayton Road campus. A small ensemble, a quiet room, and an hour of music before the weekend gets loud.

🖼️ New Ways of Seeing: American Modernism from a Private Collection
📅 Date: Monday, May 25, 2026
⏰ Time: 10:00 AM
📍 Location: 585 Park St, Naples, FL
🎨 Details: A calm holiday-Monday move through American Modernist paintings from a private Naples collection. No crowds, free admission, in and out in under an hour.

👨‍👩‍👧 Family-Friendly Activities

🐒 Gone Bananas Naples
📅 Date: Saturday, May 30, 2026
⏰ Time: 10:30 AM
📍 Location: Third Street South Farmer's Market, Naples
🍌 Details: Pop-up at the Saturday market with games, music, and a banana mascot the kids will not stop hugging. Pair it with the farmers market and you have the morning handled.

⚾ Florida Clutch 11U Tryouts
📅 Date: Saturday, May 30, 2026
⏰ Time: 9:00 AM
📍 Location: Golden Gate Community Park, Naples
🥎 Details: Saturday tryout for the Florida Clutch 11U travel team. Bring a glove, cleats, and a water bottle. Get there a few minutes early to warm up.

🥎 13U Southwest Sting Tryouts
📅 Date: Thursday, May 28, 2026
⏰ Time: 6:30 PM
📍 Location: Big Corkscrew Island Regional Park, Naples
⚾ Details: Thursday evening tryout for the 13U Southwest Sting at the new Corkscrew park. Cleats, glove, bat if you have one. Parents can catch the sunset over the fields.

🌿 Outdoor & Community

🚴 SWFL Critical Mass Naples Ride
📅 Date: Saturday, May 30, 2026
⏰ Time: 7:00 PM
📍 Location: Gordon River Greenway Parking Lot, 1596 Golden Gate Pkwy, Naples
🚲 Details: 9 interested. Group ride that rolls out of the Greenway lot at a casual pace. Lights on, helmets recommended, all bikes and all speeds welcome.

🏍️ The Hangout by Two Guys Bike Night
📅 Date: Wednesday, May 27, 2026
⏰ Time: 6:30 PM
📍 Location: 2360 Pine Ridge Rd, Naples, FL
🍔 Details: Midweek bike night on Pine Ridge. Rows of motorcycles, food, and a friendly crowd that shows up rain or shine. Roll in or just come look at the chrome.

👕 Clothing Swap at Naples Pride
📅 Date: Saturday, May 30, 2026
⏰ Time: 12:00 PM
📍 Location: Naples Pride
♻️ Details: Bring what you no longer wear, leave with something new to you. Free, low-key, and a good excuse to finally clean out the closet.

🌀 KundaFlow with Dama'De
📅 Date: Saturday, May 30, 2026
⏰ Time: 1:00 PM
📍 Location: 4949 Tamiami Trail N Suite 204, Naples, FL
🧘 Details: Kundalini-leaning flow with breathwork and movement. Bring a mat, an open hour, and leave the to-do list at the door.

💃 Hips Don't Lie: Free Workshop
📅 Date: Saturday, May 30, 2026
⏰ Time: 1:00 PM
📍 Location: 4649 Tamiami Trail North, Naples, FL
🪕 Details: 7 interested. Free Saturday dance workshop loosening up the hips, no partner and no experience needed. Come curious, leave a little less stiff.

🌅 Sunset Beach Pilates Class
📅 Date: Sunday, May 31, 2026
⏰ Time: 6:30 PM
📍 Location: Lowdermilk Beach, Naples
🏖️ Details: Mat Pilates on the sand as the sun drops over the Gulf. Bring a towel and water, arrive a few minutes early to find a flat spot.

🪑 Chair Yoga
📅 Date: Tuesday, May 26, 2026
⏰ Time: 1:00 PM
📍 Location: 4949 Tamiami Trail N Suite 204, Naples, FL
🧘 Details: Gentle chair-based class. Perfect for first-timers, recovery weeks, and anyone done with floor yoga.

⛪ Midweek Bible Study
📅 Date: Wednesday, May 27, 2026
⏰ Time: 6:30 PM
📍 Location: Naples, FL
🕊️ Details: Wednesday evening study with a small, friendly crowd. New attenders walk in every week.

⚠️ Please verify event details and availability with the respective venues or organizers, as schedules may change.

📰 What's Happening in Naples

🔗 Hurricane Season Opens June 1, Collier EM Pushing Alert Collier Sign-Ups
One week out from June 1, Collier emergency management is leaning on residents to sign up for Alert Collier and download the Collier Cares app. Now is the window to confirm your evacuation zone, stock a gallon of water per person per day, and put documents somewhere waterproof.

🔗 Vanderbilt Beach Road Extension Targets a Late-Summer Opening
The long-awaited extension runs about seven miles east from Collier Boulevard to 16th Street Northeast, with six lanes near Collier tapering to two out in the Estates and a shared-use path the whole way. Crews are laying the final asphalt and finishing new traffic signals at Wilson, Eighth Street and 16th.

🔗 Naples Pier Rebuild Clears Demolition, Eyes 2027 Reopening
The seventh rebuild of the 137-year-old pier is underway after demolition wrapped this spring, with the City Council's final design locked in. The new pier sits elevated on larger concrete pilings with a portable concession cart, and the roughly 18-month build points to a 2027 return.

🔗 Conservancy Marks 2026 Sea Turtle Nesting Season on Keewaydin and Barefoot
The Conservancy of Southwest Florida has staked the season's first loggerhead nests on Keewaydin Island and Barefoot Beach. The standing rule through the summer: lights off the sand by 9 PM and beach furniture off by 9:30.

🔗 Naples April Home Sales Notch Eleventh Straight Month of Year-Over-Year Growth
NABOR's latest report counts 966 closed sales, up 11.8 percent year over year, with $1.22 billion in dollar volume. Showings per listing climbed from 2.7 to 3.5, while homes above $3 million still offer real negotiating room.

🔗 Naples Airport Authority Election Field Fills Out Across All Five Seats
With all five board seats now headed to a countywide vote in November, candidates are filing across the board. Michelle Arnold, Rick Ruppert, Ralph Alberto and several others have entered the first-ever elected race for the authority.

🔗 Collier Planners Back Ave Maria Expansion of More Than 2,000 Acres
The Collier County Planning Commission voted nearly unanimously to recommend Ave Maria's expansion under the Rural Lands Stewardship program, clearing the way for some 6,738 new homes, retail and a senior community east of Camp Keais Road. Developers say the plan ties in 511 affordable units, most delivered off-site.

🔗 RH Naples Takes Shape at the Former Nordstrom Site in Waterside Shops
The luxury furniture brand is building out six skylit galleries plus a 4,143-square-foot, 174-seat restaurant and wine bar in the old Nordstrom box. The build is targeted to open near the end of 2026.

🔗 Connors Steak & Seafood Coming to North Naples
The steakhouse chain is opening a 10,000-square-foot location in North Naples this year, adding to its Florida footprint. It joins a long list of upscale dining names betting on the North Naples corridor.

🔗 Avenue 31 Mixed-Use Project Approved for Fifth Avenue South
A three-story building with a new restaurant and condos, backed by restaurateur Stefano Frittella, won approval to replace a single-story retail space on the Avenue. It is the latest sign that Fifth Avenue South keeps trading low-slung storefronts for vertical mixed-use.

🔗 Naples Zoo Opens South American Trail With Toco Toucan and Capybara
The new South American Trail is open with Manu the toco toucan and Izel the capybara, both transferred in on the AZA Species Survival Plan. Baird's tapir, a screamer and a coati round out the new species. Worth the midweek detour if the membership has been gathering dust.

🔗 Costco's East Naples Warehouse Targets a Fall Opening
Costco's second Collier warehouse is rising on 25 acres at Rattlesnake Hammock Road and Collier Boulevard. The 162,671-square-foot store includes a 24-pump gas station and a liquor store, with an early-fall opening in play.

🔗 FC Naples Looks to Snap a Skid as It Faces Union Omaha on May 30
Sitting around .500 on the season and working through a rough stretch, FC Naples meets Union Omaha this Saturday. The bright spot lately has been the U.S. Open Cup, where the club punched through to the second round.