🌴 What's Happening in Naples: May 4 - May 10

This is a stacked week in Naples. Cinco de Mayo lands on Tuesday and the patios on Gulf Shore, Tamiami, and Vanderbilt all turn into one big margarita zone. The Great Dock Canoe Race opens Friday at the Naples Depot and runs through Saturday. Mother's Day closes the weekend out with brunches, teas, and a beach social full of pups. Hurricane Preparedness Week is also quietly running in the background, so if you've been meaning to put together a kit, this is the nudge. Here's what's 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

🌮 Cinco de Mayo at Tequilas Naples
📅 Date: Tuesday, May 5, 2026
⏰ Time: 2:00 PM
📍 Location: Naples, FL
🌶️ Details: All-day Cinco at Tequilas with the full margarita lineup, taco specials, and a livelier crowd than the room usually pulls. 28 interested already.

🌯 The Stars Aligned: Cinco de Mayo Hits Taco Tuesday
📅 Date: Tuesday, May 5, 2026
⏰ Time: 11:00 AM
📍 Location: 4255 Tamiami Trail N, Naples, FL
🥑 Details: A rare year where Cinco lands on actual Taco Tuesday. The kitchen is leaning into it. 23 interested, 5 going, and the patio fills up fast on theme days.

🍹 Cinco de Mayo at Sunset Bar (HB's on the Gulf)
📅 Date: Tuesday, May 5, 2026
⏰ Time: 11:00 AM
📍 Location: 801 Gulf Shore Boulevard North, Naples, FL
🌅 Details: Beachfront Cinco at the Sunset Bar at HB's. Margaritas, Gulf wind, sunset in the same direction as your drink. Easy walk-in.

🍷 Good Old World Wine Tasting Event
📅 Date: Tuesday, May 5, 2026
⏰ Time: 7:00 PM
📍 Location: Naples Wine Bar
🍇 Details: A guided pour through Old World varietals from the corners of Europe most lists skip. Quieter, calmer alternative to the Cinco scene a few blocks over.

🫖 Mother's Day English Afternoon Tea
📅 Date: Sunday, May 10, 2026
⏰ Time: 3:30 PM
📍 Location: Sunburst Cafe, Naples
🌹 Details: Three tiers, finger sandwiches, scones with proper clotted cream. Reservations move fast on Mother's Day, so call ahead.

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🎵 Music & Entertainment

🪩 Cabaret in Drag Naples
📅 Date: Friday, May 8, 2026
⏰ Time: 7:00 PM
📍 Location: Dimension Event Center, Naples
✨ Details: The biggest Friday night show on the calendar by interest count. 78 marked interested, 9 going. Big costumes, sharper jokes than the title gives away, and the kind of crowd that shows up dressed for it.

🎧 Neon Rave with DJ May benefiting Wags to Wishes
📅 Date: Thursday, May 7, 2026
⏰ Time: 8:30 PM
📍 Location: Dimension Event Center, Naples
🐾 Details: A glow-stick rave with proceeds going to a local pet rescue. Wear something that picks up UV and dance for the dogs.

🎶 The ULTIMATE K-POP All-Ages Dance Party
📅 Date: Saturday, May 9, 2026
⏰ Time: 1:00 PM
📍 Location: Naples, Florida
💃 Details: All-ages K-pop dance party for the choreography crowd. Pull the kids in, learn three counts of a Stray Kids song, leave sweaty.

🤘 Shawn Theriault Music at Old Town Saloon
📅 Date: Thursday, May 7, 2026
⏰ Time: 7:00 PM
📍 Location: Old Town Saloon, Naples
🎸 Details: Local rock and roll on the saloon stage. Cold beer, no cover, easy weeknight hang.

🎵 Live Music: Jon Halmi
📅 Date: Friday, May 8, 2026
⏰ Time: 6:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎤 Details: Friday night acoustic set on Tamiami. The room runs music almost every night this week and Halmi pulls a friendly local crowd.

🎶 Live Music Saturdays: Ralph Curtis
📅 Date: Saturday, May 9, 2026
⏰ Time: 5:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🎤 Details: Saturday afternoon-into-evening set. Sit on the patio, order a second drink, stay longer than you planned.

🎼 Live Music: The Earworms
📅 Date: Sunday, May 10, 2026
⏰ Time: 2:00 PM
📍 Location: 4805 Tamiami Trail N, Naples, FL
🌷 Details: Mother's Day afternoon set. Easy mid-day move after brunch, before the long Sunday nap.

🎤 Open Mic Night at Food & Thought
📅 Date: Friday, May 8, 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.

🎲 Twisted Bingo: Music Bingo Naples
📅 Date: Monday, May 4, 2026
⏰ Time: 7:00 PM
📍 Location: Dylan's Drafthouse, Naples
🍻 Details: Music bingo to kick the week off. Free to play, drinks specials run all night.

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🎭 Arts & Theater

🎨 New Ways of Seeing: American Modernism from a Private Collection
📅 Date: Monday, May 4, 2026
⏰ Time: 10:00 AM
📍 Location: 585 Park St, Naples, FL
🖼️ Details: A new exhibition of American Modernist paintings from a private Naples collection. Quiet morning move, perfect for a slow start to the week.

📚 An Evening with Jennifer Lee & LeUyen Pham
📅 Date: Monday, May 4, 2026
⏰ Time: 6:00 PM
📍 Location: Norris Center, Naples
✍️ Details: The Frozen co-director and the Princess in Black illustrator on one stage. A storytellers' night in Cambier Park, lovely for parents and kid-lit fans.

🎭 Much Ado About Nothing at the Naples Players
📅 Date: Wednesday, May 6, 2026
⏰ Time: 7:30 PM
📍 Location: 701 5th Ave S, Naples, FL
🎭 Details: Shakespeare's sharpest rom-com on the Sugden stage. Crisp pace, big laughs, and 8 already interested before tickets really moved.

🌟 EBN & NAD Red Carpet Opening Night at Naples Players
📅 Date: Wednesday, May 6, 2026
⏰ Time: 6:30 PM
📍 Location: Naples Players Sugden Theater
🥂 Details: Red carpet opening with a champagne hour and the local theater crowd. Dress up. Take the photos.

🎶 Beautiful: The Carole King Musical (ASL Interpreted)
📅 Date: Saturday, May 9, 2026
⏰ Time: 2:00 PM
📍 Location: Gulfshore Playhouse, Naples
🎹 Details: An ASL-interpreted matinee of the Tony-winning Carole King musical. Worth the ticket alone, the interpretation makes the front section the best seat in the house.

🎬 NIAF Italian Movie Night at Paragon Pavilion
📅 Date: Thursday, May 7, 2026
⏰ Time: 6:30 PM
📍 Location: Paragon Theaters, Naples
🍷 Details: Mother's Day weekend treat from the National Italian American Foundation. Italian cinema, espresso, and the warm Paragon crowd that always shows up.

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👨‍👩‍👧 Family-Friendly Activities

👮 NPD's 3rd Annual Safety Fair & Family Fun Day
📅 Date: Saturday, May 9, 2026
⏰ Time: 9:00 AM
📍 Location: Baker Park, Naples
🚓 Details: Naples PD throws the doors open at Baker Park. K-9 demos, fire trucks, bounce houses, free hot dogs, the whole deal. 51 interested, 8 going.

💼 Biz Kidz Expo 2026
📅 Date: Saturday, May 9, 2026
⏰ Time: 11:00 AM
📍 Location: Coastland Center, Naples
🚀 Details: The biggest family event of the week by interest count. 75 interested, 15 going. Kid entrepreneurs sell, pitch, and run their own booths inside the mall. Free entry.

🌷 6th Annual Mother's Day Celebration
📅 Date: Saturday, May 9, 2026
⏰ Time: 3:00 PM
📍 Location: Naples United Church of Christ
🌸 Details: A community Mother's Day afternoon with food, music, and door prizes. Free and open to all.

🐶 Mother's & Pups Social at Lowdermilk Park
📅 Date: Saturday, May 9, 2026
⏰ Time: 11:00 AM
📍 Location: 1301 Gulf Shore Blvd N, Naples
🐕 Details: Bring mom, bring the dog, bring a beach blanket. Lowdermilk on a Saturday in May is hard to beat.

🐒 Gone Bananas Naples
📅 Date: Saturday, May 9, 2026
⏰ Time: 10:30 AM
📍 Location: Third Street South Farmer's Market, Naples
🍌 Details: A pop-up at the Saturday market with games, music, and a banana mascot the kids will not stop hugging.

🫖 The Magical Teapot Party at Barnes & Noble
📅 Date: Saturday, May 9, 2026
⏰ Time: 11:00 AM
📍 Location: Barnes & Noble, Naples
✨ Details: Storytime tea party for the small kids. Bring a cup, listen to a story, walk out with a new favorite book.

🎓 The Kindergarten Experience
📅 Date: Thursday, May 7, 2026
⏰ Time: 5:00 PM
📍 Location: 215 Airport Pulling Rd N, Naples, FL
✏️ Details: A walk-through of what kindergarten actually looks like, for parents whose kid starts in August. Quiet but the questions in the room are gold.

🎓 2026 LCF Graduation: Associate Leadership Collier & Leadership Collier
📅 Date: Monday, May 4, 2026
⏰ Time: 5:00 PM
📍 Location: Gulfshore Playhouse, Naples
🎉 Details: Class of 2026 graduation for two of the most active community-leadership programs in Collier. 21 going, 18 interested.

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🌿 Outdoor & Community

🛶 The Battle of the Paddle: Great Dock Canoe Race Opening Ceremony
📅 Date: Friday, May 8, 2026
⏰ Time: 5:00 PM
📍 Location: Naples Depot
🚤 Details: The opening night of the Great Dock Canoe Race weekend. Music, food trucks, and the boats coming in to stage for Saturday's race. 7 interested.

🚣 Battle of the Paddle: Race Day Exhibit
📅 Date: Saturday, May 9, 2026
⏰ Time: 9:00 AM
📍 Location: Naples Depot
🌊 Details: Race day exhibit with the boats on display, gear demos, and locals running through the warm-up paddles. Bring a folding chair.

🥬 Third Street South Farmers Market
📅 Date: Saturday, May 9, 2026
⏰ Time: 7:30 AM
📍 Location: Third Street South Farmer's Market, Naples
🍓 Details: The Mother's Day weekend market. Best place in town to grab the bouquet, the bakery box, and the bottle of cold-pressed juice for tomorrow.

⛳ 6th Annual Literacy Collier Golf Scramble
📅 Date: Friday, May 8, 2026
⏰ Time: 8:30 AM
📍 Location: The Rookery at Marco by Marriott
📚 Details: Charity scramble that funds adult literacy in Collier County. 2 going, 2 interested, but these always fill out by tee time.

🤝 May Networking & Connections Event Naples
📅 Date: Tuesday, May 5, 2026
⏰ Time: 5:00 PM
📍 Location: The Hangout by Two Guys, Naples
🥂 Details: 40 interested. The reliable monthly Naples networking happy hour, with a Cinco-night twist this round.

🎖️ Veterans Support Group at Fleischmann Park
📅 Date: Thursday, May 7, 2026
⏰ Time: 1:30 PM
📍 Location: Fleischmann Park, Naples
🇺🇸 Details: Open peer support group for local vets. Coffee, conversation, no pressure.

🧘 Y6 Spanish Flow & Spanish Yoga Nidra
📅 Date: Saturday, May 9, 2026
⏰ Time: 1:00 PM
📍 Location: 4649 Tamiami Trail North, Naples, FL
✨ Details: A bilingual Saturday flow and a guided Spanish Yoga Nidra to close the practice. New format, friendly room.

🪑 Chair Yoga
📅 Date: Tuesday, May 5, 2026
⏰ Time: 1:00 PM
📍 Location: 4949 Tamiami Trail N, Suite 204, Naples
🧘 Details: Gentle chair-based class. Perfect for first-timers, recovery weeks, and anyone who's done with floor yoga.

✋ Reiki Share
📅 Date: Saturday, May 9, 2026
⏰ Time: 1:00 PM
📍 Location: 4949 Tamiami Trail N, Suite 204, Naples
🌿 Details: Drop-in reiki circle, all levels welcome. Quiet, restorative, hour and change.

👗 Fashion Friday
📅 Date: Friday, May 8 through Friday, May 15, 2026
📍 Location: 4351 Tamiami Trail North, Naples, FL
👜 Details: Pop-up styling event with new arrivals and a glass of something cold while you browse. Walk-in friendly.

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

📰 What's Happening in Naples

🔗 Naples City Council Begins Formal Dispute Over Airport Authority Law
Council voted to start the Chapter 164 conflict-resolution process with the state over HB 4005, the law that shifts Naples Airport Authority oversight from city-appointed seats to a county-elected board. The city argues the new law undermines the $1-a-year, 731-acre lease that runs through 2068, which could clear a path to litigation.

🔗 Friends of Naples Airport Sues City Over Development Restrictions
The pro-airport advocacy group filed suit over a recent council resolution tightening development controls at Naples Municipal. The case lands at the same time as the council's formal dispute over the new state authority law, putting the airport on two legal tracks at once.

🔗 Naples Mayor Heitmann Granted $10K Bond After Probation Violation Arrest
Mayor Teresa Heitmann was booked April 20 on a probation-violation charge tied to a routine drug screening she has publicly disputed. A judge set bond at $10,000 the next morning. She remains in office while the case plays out.

🔗 First Sea Turtle Nest of 2026 Recorded on Barefoot Beach
A loggerhead made the first recorded nest of the season, staked and monitored by the Collier Sea Turtle Protection Team. They patrol 22.5 miles of coastline daily through October. Reminder for evening beach walks: no flashlights, fill in any holes.

🔗 Hurricane Preparedness Week Runs May 3-9
NOAA, the Florida Division of Emergency Management, and local agencies are running Hurricane Preparedness Week the same week as this newsletter. Season opens June 1. If you haven't checked your kit, your evacuation zone, or your insurance since last year, this is the week.

🔗 Picayune Strand Wildfire Reaches 60 Percent Containment After 1,733 Acres Burned
The brush fire south of I-75 ran through more than 1,700 acres before two Black Hawk helicopters and crews from a dozen agencies pushed containment up. Roughly 164 homeowners had been told to evacuate during the peak, with the Golden Gate Community Center serving as a pet-friendly shelter.

🔗 Vanderbilt Beach Road Extension on Track for Summer Open
The 7-mile extension from Collier Boulevard to 16th Street NE in Golden Gate Estates is set to open in late spring or early summer. New signals at Wilson, 8th Street NE, and 16th come online with it. The Cypress Canal relocation is wrapping up in parallel.

🔗 Collier Commissioners Raise Short-Term Borrowing Cap to $300 Million
The board lifted the short-term borrowing ceiling from $200M to $300M to bridge water and wastewater expansion ahead of long-term financing. Total infrastructure investment in the pipeline is now north of $438 million.

🔗 Collier Buys 1.5 Miles of Rail Corridor for Bonita Estero Trail
Commissioners signed off on $11.6 million to acquire roughly 24 acres of the Seminole Gulf Railway corridor for the future Bonita Estero Rail Trail. The corridor eventually feeds a 400-mile multi-use trail running all the way up to Tampa.

🔗 Naples Council Sets Aside $1.27M for Downtown Event Safety Barriers
Council earmarked $1,270,544 in uncommitted funds to buy permanent crowd and vehicle barriers for events on city property. The vote sets up the next round of permit decisions for downtown events through the rest of 2026.

🔗 NPAC Stages First-Ever Adult Production With "Next to Normal" May 14-16
Naples Performing Arts Center is putting up its first adult production at the Norris Center the weekend after this one. The Pulitzer- and Tony-winning rock musical is a tonal departure for NPAC and tickets are moving.

🔗 Roma Italian Bistro Relaunches as Ottimo on 5th Cucina & Bar
The longtime Fifth Avenue South Italian spot rebranded into the former KJ Sushi space as Ottimo on 5th. New look, refreshed menu, same neighborhood standby.

🔗 Naples Restaurant Owner Installs Inflatable Flood Barriers Ahead of Hurricane Season
Alberto's on Fifth installed a new inflatable flood-barrier system after Hurricane Ian. The technology has drawn interest from other downtown operators with low elevation and water at the back door every named storm.

🔗 Naples Leads Region in Pending and Closed Home Sales as Inventory Loosens
The latest NABOR market data has Naples posting double-digit year-over-year gains in both pending and closed sales. Single-family medians are easing, condo inventory is climbing, and time-on-market is creeping up. The tilt is slow and uneven, but it's tilting.