The Naples Pulse Weekly
Curated local events for Naples, by interest
Good morning, Naples.
This is a quieter Naples week after the holiday weekend, which makes the good plans easier to spot: Art After Hours tonight at The Baker Museum, a run of food-tour and waterfront options, live music at Rooftop and Compass Margaritaville, polished brunch choices for the weekend, and two sports notes to keep on your radar.
This week's big picture: Art After Hours is the clean midweek anchor, food tours and water outings are the visitor-friendly lane, Compass and Rooftop carry the casual live-music calendar, and sports readers should circle FC Naples while keeping an eye on the Everblades playoff schedule.
If you only make one plan, start with tonight's Art After Hours. If you are building the weekend, use the quick picks near the bottom.
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This Week's Headliner
Art After Hours
Wednesday, May 27 | 6:00 PM to 9:00 PM | The Baker Museum at Artis-Naples
Event info: https://artisnaples.org/events/visual-arts-events/art-after-hours
Art After Hours is the easiest cultural pick of the week: free museum admission, an evening window, and live music at The Baker Museum. It is polished without being a full dinner-and-show production, and it works whether you stay for an hour or make it the center of the night.
Music & Live Entertainment
Art After Hours
Wednesday, May 27 | 6:00 PM to 9:00 PM | The Baker Museum at Artis-Naples
Event info: https://artisnaples.org/events/visual-arts-events/art-after-hours
Free museum admission plus live music makes this the strongest midweek arts-and-music pick.
Motown Ross Brown at Rooftop
Thursday, May 28 | 5:00 PM to 7:00 PM | Rooftop at Riverside
Info: https://www.visitnaplesfl.com/event/motown-ross-brown-at-rooftop/2026/05/28
An easy early-evening music stop before dinner.
Live Music at Compass Margaritaville
Thursday, May 28 through Saturday, May 30 | Evening sets | Compass Hotel by Margaritaville Naples
Info: https://www.visitnaplesfl.com/events
Theater & Performing Arts
Oliver!
Opening Thursday, June 4 | TheatreZone
Info: https://www.visitnaplesfl.com/event/oliver/2026/06/04
This opens just after the May 27 to June 3 issue window, but it is the theater note to put on the calendar now.
Beautiful: The Carole King Musical
Through Sunday, May 31 | Gulfshore Playhouse
Tickets / info: https://www.gulfshoreplayhouse.org/shows-events/beautiful-the-carole-king-musical/
If you have been meaning to catch this one, this is the final week. Familiar music, broad appeal, and a polished Gulfshore setting make it a safe theater pick for visiting family or a date night.
Food & Dining
Feast on 5th: Naples Food Tour
Wednesday, May 27, Sunday, May 31, and Wednesday, June 3 | 12:00 PM to 3:00 PM | Paradise Food Tours
Info: https://www.visitnaplesfl.com/event/feast-on-5th-naples-food-tour/2026/05/27
A structured Fifth Avenue outing for visitors, newer residents, or locals who want downtown handled for them. Useful when you want a daytime plan that still feels like Naples.
Weekend Brunch at Taberna
Saturday, May 30 and Sunday, May 31 | 11:00 AM to 3:00 PM | Taberna Burntwood
Info: https://www.visitnaplesfl.com/event/weekend-brunch-at-taberna/2026/05/30
Champagne Brunch at Sails
Saturday, May 30 and Sunday, May 31 | 11:30 AM to 4:00 PM | Sails Restaurant
Info: https://www.visitnaplesfl.com/event/saturday-champagne-brunch/2026/05/30
Arts & Culture
Art After Hours
Wednesday, May 27 | 6:00 PM to 9:00 PM | The Baker Museum at Artis-Naples
Event info: https://artisnaples.org/events/visual-arts-events/art-after-hours
The week's best arts pick: free admission, evening hours, and a museum setting that works even if you only stay for part of it.
Flamingo Island Flea Market
Friday, May 29 through Sunday, May 31 | 8:00 AM to 4:00 PM | Bonita Springs
Info: https://www.visitnaplesfl.com/event/flamingo-island-flea-market/2026/05/29
Downtown Bonita Springs Walking History Tour
Wednesday, May 27 and Thursday, May 28 | Historic McSwain Home Museum and Gardens
Info: https://www.visitnaplesfl.com/event/the-downtown-bonita-springs-walking-history-tour/2026/05/27
Boating & Water Sports
Naples Princess Sightseeing Cruises
Daily | Port-O-Call Way
Info: https://www.visitnaplesfl.com/event/naples-princess-cruises/2026/05/27
Pure Florida Sightseeing Excursions
Daily | Tin City
Info: https://www.visitnaplesfl.com/event/pure-florida-daily-sightseeing-excursions/2026/05/27
Naples Bay Water Shuttle
Daily | Noon to 8:00 PM | Naples waterfront
Info: https://www.visitnaplesfl.com/event/naples-bay-water-shuttle/2026/05/27
Good as a lunch add-on, visitor activity, or casual waterfront loop when the weather cooperates.
Golf & Sports
FC Naples vs. Charlotte Independence
Wednesday, June 3 | 7:30 PM | Paradise Coast Sports Complex
Info: https://www.fcnaples.com/schedule/
This is the local sports pick inside the issue window.
Florida Everblades Eastern Conference Finals Watch
Monday, June 1 and Wednesday, June 3 | 7:30 PM | Hertz Arena, if necessary
Info: https://www.floridaeverblades.com/schedule
Treat these as playoff-watch plans: worth flagging for sports readers, but check the series status before buying tickets or heading to Estero.
Outdoor & Nature
Naples Botanical Garden
Daily | Bayshore Drive
Info: https://www.naplesgarden.org/
Late May is a morning-first garden season.
Waterfront Sightseeing
Daily | Naples Bay, Tin City, and Port-O-Call Way
Naples Princess, Pure Florida, and the Naples Bay Water Shuttle all work for a low-friction outdoor plan when the forecast cooperates.
Tuesday Night Tuck-In on the Farm
Tuesday, June 2 | 3:30 PM to 5:30 PM | Empowerment Farm
Info: https://www.visitnaplesfl.com/event/tuesday-night-tuck-in-on-the-farm/2026/06/02
Quick Picks: Plan the Week
Wednesday: Art After Hours, Feast on 5th, Wooftop Wednesday, and Twisted Bingo at Rooftop.
Thursday: Motown Ross Brown, live music at Compass Margaritaville, Experience Bonita Springs Food Tour, and Trivia Night at Rooftop.
Friday: Live Music Fridays at Compass Margaritaville, Flamingo Island Flea Market, and waterfront sightseeing.
Saturday: Champagne Brunch at Sails, Weekend Brunch at Taberna, Flamingo Island Flea Market, live music at Compass, and Experience Bonita Springs Food Tour.
Sunday: Beautiful closes at Gulfshore Playhouse, Feast on 5th food tour, Champagne Brunch at Sails, Brunch with a Roar at Tigress, and waterfront sightseeing.
Coming Up
May 27: Art After Hours at The Baker Museum
May 30: Pro-Am Series at Artis-Naples
May 31: Beautiful closes at Gulfshore Playhouse
June 1: Everblades Eastern Conference Finals Game 6 at Hertz Arena, if necessary
June 3: FC Naples vs. Charlotte Independence at Paradise Coast Sports Complex
June 3: Everblades Eastern Conference Finals Game 7 at Hertz Arena, if necessary
June 4: Oliver! opens at TheatreZone
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