🌴What's Happening in Naples May 18 - May 24

Memorial Day weekend lands at the back end of the week and the calendar reflects it. Three Latin music nights cluster at the East Tamiami lounge: an all-white kickoff Friday, a banda blowout that same night, and a Tribal versus Huapango dance battle Sunday. The Naples Players close out Much Ado About Nothing midweek, the 24th Annual Ride of Silence rolls through Cambier Park on Wednesday, and Rise and Connect packs Inn on Fifth Thursday morning. Bayfront patios on Tamiami North run music almost every night. Hurricane season opens in two weeks, sea turtles are nesting, and Sprouts finally opened up on Logan. 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

🍷 "Mediterranean Characters" Wine Tasting Event
📅 Date: Tuesday, May 19, 2026
⏰ Time: 7:00 PM
📍 Location: Naples Wine Bar
🍇 Details: A guided pour through Mediterranean varietals with the bar's resident pourer doing the storytelling. Smaller, smarter crowd than the average tasting.

🥬 Third Street South Farmers Market
📅 Date: Saturday, May 23, 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.

🍸 Naples Connect
📅 Date: Wednesday, May 20, 2026
⏰ Time: 5:30 PM
📍 Location: Aqua on Fifth, Naples
🥂 Details: 44 interested, 10 going. The biggest midweek mixer of the month. Rooftop networking with a young professional crowd, two drink tickets at the door.

🍑 Collier Fruit Growers Meeting
📅 Date: Monday, May 18, 2026
⏰ Time: 6:00 PM
📍 Location: Collier County Golden Gate Community Center
🍌 Details: Monthly meeting of the local tropical fruit growers club. Tastings, swap of cuttings, and the most knowledgeable mango people in Southwest Florida.

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🎵 Music & Entertainment

Memorial Day Weekend - Texas VS Florida Tribal VS Huapango Dance Competition
📅 Date: Sunday, May 24, 2026
⏰ Time: 9:00 PM
📍 Location: 2634 Tamiami Trail E, Naples, FL
💃 Details: The flagship Memorial Day weekend party at the East Tamiami lounge. Texas dancers against Florida dancers, Tribal style against Huapango, full live banda and a crowd that takes the dance floor seriously.

🤍 The 54 Experience - All White Weekend
📅 Date: Friday, May 22, 2026
⏰ Time: 6:00 PM
📍 Location: 2634 Tamiami Trail E, Naples, FL
🪩 Details: 25 already interested. Studio 54 inspired all-white dress code, late night DJs, and the unofficial kickoff to the long weekend on East Tamiami.

🎺 Celebrando Memorial Day Weekend - A Ver De Qué Lado Suena La Banda
📅 Date: Friday, May 22, 2026
⏰ Time: 10:00 PM
📍 Location: 2634 Tamiami Trail E, Naples, FL
🎶 Details: Live banda night with two acts trading sets to see whose horn section pulls the bigger crowd reaction. Late start, late finish, dress comfortable for the floor.

🌴 Reggae Pool Party at Wahoo's
📅 Date: Friday, May 22, 2026
⏰ Time: 6:30 PM
📍 Location: Wahoo's River Bar and Grill, Naples
🍹 Details: 15 interested, 4 going. Poolside reggae set on the river, frozen drinks, no shoes required. Easy Friday move before the East Tamiami crowd gets going.

🎤 Chelo Chelo Live in Naples Florida
📅 Date: Monday, May 18, 2026
⏰ Time: 7:00 PM
📍 Location: Naples, FL
🪗 Details: Monday night live set from the Latin singer-songwriter. Smaller room than he usually plays, easy walk-in.

🎸 Live Music Fridays: Head Above Water
📅 Date: Friday, May 22, 2026
⏰ Time: 6:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎶 Details: Friday night patio set on Tamiami. The room runs music almost every night this week and Head Above Water is the band the regulars show up for.

🎶 Live Music Sundays: Head Above Water
📅 Date: Sunday, May 24, 2026
⏰ Time: 2:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🌞 Details: Same band, Sunday afternoon vibe. The shaded patio fills up fast on holiday weekends, so get there before three.

🎵 Live Music with Dockside Duo
📅 Date: Thursday, May 21, 2026
⏰ Time: 6:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎤 Details: Thursday night acoustic duo on the patio. Two singers, two guitars, a setlist that runs from Eagles to Jack Johnson without slowing the room.

🎸 Live Music with Joe Marino
📅 Date: Saturday, May 23, 2026
⏰ Time: 5:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎶 Details: Saturday afternoon-into-evening set from a steady local. The kind of show you walk into for one drink and stay for three.

🎤 Open Mic Night at Food & Thought
📅 Date: Friday, May 22, 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 into the second half of the night.

🪩 Take Me Thur There at Dimension Night Club
📅 Date: Sunday, May 24, 2026
⏰ Time: 12:00 AM
📍 Location: Dimension Night Club, Naples
💿 Details: Midnight rollover into Memorial Day at Dimension. Late ticket, dance-floor crowd, the closing move for anyone running long off East Tamiami.

🎲 Monday Trivia on Marco Island
📅 Date: Monday, May 18, 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 18, 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

🎭 Much Ado About Nothing at the Naples Players
📅 Date: Wednesday, May 20, 2026
⏰ Time: 7:30 PM
📍 Location: 701 5th Ave S, Naples, FL
✨ Details: Final week of the run at the Kizzie Theater. Shakespeare's sharpest rom-com, crisp pace, big laughs. Last call before it closes Sunday.

🖼️ New Ways of Seeing: American Modernism from a Private Collection
📅 Date: Monday, May 18, 2026
⏰ Time: 10:00 AM
📍 Location: 585 Park St, Naples, FL
🎨 Details: Quiet Monday morning move through American Modernist paintings from a private Naples collection. Calm room, no crowds, free admission to the gallery.

🍽️ Paint-a-Plate at Baker Senior Center
📅 Date: Tuesday, May 19, 2026
⏰ Time: 5:30 PM
📍 Location: Baker Senior Center Naples
🎨 Details: 6 interested, 2 going. Paint a ceramic plate, fire it at the studio, pick it up the following week. All supplies included.

👨‍👩‍👧 Family-Friendly Activities

🐒 Gone Bananas Naples
📅 Date: Saturday, May 23, 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.

🎮 Retro Game Night at Naples Depot
📅 Date: Friday, May 22, 2026
⏰ Time: 5:00 PM
📍 Location: Naples Depot
🕹️ Details: 5 interested, 2 going. NES, Sega Genesis, an old CRT, and pizza on a folding table at the train depot. Bring the kids, bring the snacks.

⚾ Florida Clutch 11U Tryouts
📅 Date: Monday, May 18, 2026
⏰ Time: 6:00 PM
📍 Location: Naples, FL
🥎 Details: Monday tryout for the Florida Clutch 11U travel team. Bring a glove, cleats, and a water bottle.

🌿 Outdoor & Community

🚴 24th Annual Ride of Silence
📅 Date: Wednesday, May 20, 2026
⏰ Time: 6:00 PM
📍 Location: Cambier Park, Naples
🕊️ Details: 10 interested. Silent group ride through downtown to honor cyclists killed or injured on the roads. Bikes meet at Cambier, no entry fee, slow pace.

🚶 God Girl Walk
📅 Date: Saturday, May 23, 2026
⏰ Time: 8:30 AM
📍 Location: Baker Park, Naples
☕ Details: 15 interested, 5 going. Saturday morning women's walk-and-talk through Baker Park. Coffee after, no pace pressure, brings new faces every week.

🧘 Rise and Connect
📅 Date: Thursday, May 21, 2026
⏰ Time: 9:00 AM
📍 Location: Inn on Fifth, Naples
☀️ Details: 34 interested, 9 going. The biggest Thursday morning move in town. Networking breakfast at Inn on Fifth, light yoga and breathwork, coffee and intros after.

🌸 Slow Flow and Sound Bath
📅 Date: Saturday, May 23, 2026
⏰ Time: 1:00 PM
📍 Location: 4649 Tamiami Trail North, Naples, FL
🔔 Details: 8 interested. Gentle Saturday flow followed by a singing-bowl sound bath. Bring a blanket, an open hour, and don't plan anything urgent after.

🪑 Chair Yoga
📅 Date: Tuesday, May 19, 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.

📖 Love Yoga Center Book Club: The Untethered Soul
📅 Date: Monday, May 18, 2026
⏰ Time: 7:30 PM
📍 Location: 4949 Tamiami Trail N Suite 204, Naples, FL
📚 Details: 4 interested, 1 going. Monthly book club working through Singer's Untethered Soul. Show up even if you only read half.

⛪ Midweek Bible Study
📅 Date: Wednesday, May 20, 2026
⏰ Time: 6:30 PM
📍 Location: Naples, FL
🕊️ Details: Wednesday evening study with a small, friendly crowd. New attenders walk in every week.

🩺 Naples Community Breast Ultrasound Screening
📅 Date: Wednesday, May 20, 2026
⏰ Time: 8:30 AM
📍 Location: OMNI Balanced Life Center, Naples
💕 Details: Wednesday morning community breast ultrasound clinic. Walk-in friendly, registration on site, free if you qualify.

⚖️ Family Law Seminar
📅 Date: Friday, May 22, 2026
⏰ Time: 8:15 AM
📍 Location: 3315 Tamiami Trail East, Naples, FL
📝 Details: Free morning seminar on Florida family law basics. Practical, not pushy, hosted by a local firm.

❤️ Love from the Inside Out at Trinity by the Cove
📅 Date: Friday, May 22 through Saturday, May 23, 2026
📍 Location: Trinity by the Cove Episcopal Church, Naples
🙏 Details: Two-day women's retreat at Trinity by the Cove. Morning sessions Friday and Saturday, lunch included both days, open to all comers.

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

📰 What's Happening in Naples

🔗 Newman Drive Brush Fire Hits 1,733 Acres in East Naples, Containment Climbs to 60%
The Newman Drive Fire near Alligator Alley pushed past 1,700 acres before crews knocked containment up to 60 percent. Evacuations were lifted along Stable Way, Benfield, Beck Boulevard and Le Buff Road. Golden Gate Community Center stayed open as a pet-friendly safe haven during the worst of it. Air quality alerts are still landing during inversion mornings.

🔗 Sprouts Farmers Market Opens at Ridgeport Plaza in North Naples
Sprouts opened Thursday at 5351 Airport-Pulling Road in Ridgeport Plaza, the chain's second Collier location after the 2019 Logan Landings store. The 24,491-square-foot build sits in the old Bed Bath & Beyond box. Golf Galaxy follows into the same plaza late summer.

🔗 Conservancy Stakes First 2026 Sea Turtle Nest on Keewaydin Island
The Conservancy of Southwest Florida found a loggerhead nest on Keewaydin on April 28, with another staked the next day on Barefoot Beach. The Conservancy has been monitoring Keewaydin since 1983. Standing rule for the season: lights off the sand by 9 PM, beach furniture off by 9:30.

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

🔗 Costco's East Naples Build Targets Fall Ribbon Cutting at Rattlesnake Hammock and Collier
Costco's second Collier warehouse is targeted to break ground this spring on 25 acres at Rattlesnake Hammock Road and Collier Boulevard. The 162,671-square-foot store includes a 24-pump gas station and a 2,000-square-foot liquor store. Construction runs about 100 to 110 days, so an early-fall opening is in play.

🔗 DeSantis Signed HB 4005, Naples Airport Authority Now Headed to County-Wide Election
All five Naples Airport Authority seats are now elected as of the November general election. Three seats are reserved for city residents, two for unincorporated Collier. Candidates are already filing. The new law is the trigger for the city's Chapter 164 dispute and the active Friends of Naples Airport lawsuit.

🔗 Naples Airport Authority Election Field Takes Shape, Michelle Arnold Files
Former Collier code enforcement director Michelle Arnold opened her campaign for one of the first elected Naples Airport Authority seats. Several other candidates have filed across both city and unincorporated tracks. The August primary sets the runoff field for November.

🔗 Naples April Home Sales Notch Eleventh Straight Month of Year-Over-Year Growth
NABOR's April report counts 966 closed sales, up 11.8% from last April, with $1.22 billion in dollar volume. Showings per listing climbed from 2.7 to 3.5, the biggest jump across the five-city tracking area. Inventory still sits at 5.4 months on single-family and 7.5 on condos.

🔗 Naples Mayor Heitmann Pleaded Not Guilty May 11 in Probation Violation Case
Mayor Teresa Heitmann's arraignment landed last Monday on the cannabinoid-positive probation violation tied to her 2024 DUI plea deal. Her attorney has entered a not-guilty plea and is pointing to two independent negative samples from late March. Bond stays at $10,000 with weekly check-ins.

🔗 Naples Players Close Out 72nd Season With Final Week of Much Ado About Nothing
The Naples Players run the final shows of Much Ado About Nothing in the Kizzie Theater this week, closing the 72nd season Sunday. The 73rd season schedule drops alongside subscription renewals once the run wraps.

🔗 Donna Fiala Eagle Lakes Community Park Officially Renamed in East Naples
Collier commissioners renamed the East Naples park between Naples Manor and Lely Resort to honor former district commissioner Donna Fiala. The park sits off U.S. 41 East and keeps all current programming and field rentals.

🔗 Fifth Avenue South Adds Prime Social Reserve, Barrio Taqueria, All Too Well
Three new concepts have hit the Avenue this spring. Prime Social Reserve runs a 7,300-square-foot indoor-outdoor build at 837 with a rooftop elevator. Barrio Taqueria opens esquites and empanadas at 539. All Too Well, the gourmet sandwich shop on the Eighth Street corner, has been pulling lines since February.

🔗 Hurricane Season Opens June 1, Collier EM Pushing Alert Collier Sign-Ups
Two weeks out from June 1, Collier emergency management is leaning on residents to sign up for Alert Collier and download the Collier Cares app. CSU's outlook calls for 13 named storms, 8 hurricanes, 2 majors. Special Needs Shelter registrations are open through county Emergency Management.

🔗 Superintendent Leslie Ricciardelli's Contract Ends June 2026, Decision in New Board's Hands
Collier County Public Schools Superintendent Leslie Ricciardelli's three-year contract runs out next month. Three school board seats are on the ballot this year, with the August primary on the 18th and the general in November. The renewal call lands with whoever wins.

🔗 FC Naples Drops Home Match to Reigning USL League One Champion One Knoxville
More than 3,000 fans packed Paradise Coast Sports Complex earlier this month as FC Naples hosted defending USL League One champ One Knoxville SC. Naples controlled 63.7% of possession but fell 0-3. The club hits the road through May before returning home in early June.