Thursday, August 6 | 5:00 PM to 7:00 PM | Rooftop at Riverside

An early, social music stop with classic Motown favorites. It is useful when you want some energy without committing the whole night.

Info: https://www.visitnaplesfl.com/event/motown-ross-brown-at-rooftop/2026/08/06

Thursday, August 6 and Friday, August 7 | 6:00 PM to 9:00 PM; Saturday, August 8 | 5:00 PM to 8:00 PM | Compass Hotel by Margaritaville Naples

Compass is the flexible music option this week. Use it for an easy drink, a casual meet-up, or somewhere to land after dinner.

Info: https://www.visitnaplesfl.com/events

Monday, August 10 | 7:00 PM to 10:00 PM | The Oasis

A low-pressure Monday option for readers who like informal local music and a full kitchen nearby.

Info: https://www.visitnaplesfl.com/event/open-mic-night-with-bryan-steve/2026/08/10

Wednesday, August 5 | Artis-Naples

This week's strongest performing-arts choice is musical rather than theatrical. The Beach Boys tribute is familiar, polished, and easy to build into a midweek night out.

Info: https://artisnaples.org/events/sail-on

Wednesday, August 5 and Sunday, August 9 | 12:00 PM to 3:00 PM | Fifth Avenue South

A structured downtown outing for visitors, newer residents, or locals who want the lunch plan handled for them.

Info: https://www.visitnaplesfl.com/event/feast-on-5th-naples-food-tour/2026/08/05

Friday, August 7 and Tuesday, August 11 | 11:00 AM to 2:00 PM | Paradise Food Tours

This combines tastings with local history and gives readers willing to go north a daytime plan with a clear beginning and end.

Info: https://www.visitnaplesfl.com/event/experience-bonita-springs-food-tour/2026/08/07

Saturday, August 8 and Sunday, August 9 | Taberna, Sails, and Tigress

Taberna is the practical choice, Sails is the occasion brunch, and Tigress adds a rooftop setting on Sunday. Pick the mood first, then reserve.

Info: https://www.visitnaplesfl.com/events

Wednesday, August 5 | 2:00 PM to 3:00 PM; Thursday, August 6 | 10:00 AM to 11:00 AM | Historic McSwain Home Museum and Gardens

A compact local-history outing. Thursday morning is the more comfortable summer slot.

Info: https://www.visitnaplesfl.com/event/the-downtown-bonita-springs-walking-history-tour-2/2026/08/06

Friday, August 7 through Sunday, August 9 | 8:00 AM to 4:00 PM | Bonita Springs

Go early for casual treasure hunting before the day heats up. This is browsing, not a polished event, which is part of the appeal.

Info: https://www.visitnaplesfl.com/event/flamingo-island-flea-market/2026/08/07

Wednesday, August 5 | 7:30 PM | Paradise Coast Sports Complex

FC Naples gives Wednesday night a local sports anchor. It is the week's clearest family-friendly option for readers who want energy, a crowd, and a defined start time.

Info: https://www.fcnaples.com/schedule/

Daily | 10:00 AM to 8:00 PM | 550 Port O Call Way

A reliable Naples plan for visiting family or a low-effort water day. Check the day's departure schedule before heading over.

Info: https://www.visitnaplesfl.com/event/naples-princess-cruises/2026/08/05

Daily | 10:00 AM to 8:00 PM | Tin City

Another flexible route onto the water, with lunch and browsing nearby. Keep the rest of the day loose.

Info: https://www.visitnaplesfl.com/event/pure-florida-daily-sightseeing-excursions/2026/08/05

Saturday, August 8 | 9:00 AM to 1:00 PM | Empowerment Farm, 2600 Garland Rd

The farm opens for animal encounters, food-forest tours, grounds exploration, and its market. Arrive toward the front of the window for the most comfortable version.

Info: https://www.visitnaplesfl.com/event/second-saturdays-open-farm/2026/08/08

Daily | Bayshore Drive

Still one of Naples' strongest daytime choices, provided you treat it as a morning plan and move lunch indoors.

Info: https://www.naplesgarden.org/