Thursday, July 23 | 5:00 PM to 7:00 PM | Rooftop at Riverside

This is the cleanest live-music pick of the week: early, social, and finished before the night gets heavy. Use it as the front half of dinner plans, especially if you want something lively without making the evening too formal.

Info: https://www.visitnaplesfl.com/event/motown-ross-brown-at-rooftop/2026/07/23

Thursday, July 23 and Friday, July 24 | 6:00 PM to 9:00 PM | Compass Hotel by Margaritaville Naples

Compass is the flexible music backup for the week. It works after dinner, with visitors, or when you want a little atmosphere without tickets, parking stress, or a long drive.

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

Saturday, July 25 | 5:00 PM to 8:00 PM | Compass Hotel by Margaritaville Naples

This is the more relaxed Saturday version. It gives you an early evening option before a late dinner or an easy place to land when the day has been mostly errands and air conditioning.

Info: https://www.visitnaplesfl.com/event/live-music-saturdays/2026/07/25

Monday, July 27 | 7:00 PM to 10:00 PM | The Oasis

A casual local room for readers who like an informal music night. Best treated as a light Monday option, not the centerpiece of the week.

Info: https://www.visitnaplesfl.com/event/open-mic-night-with-bryan-steve/2026/07/27

Wednesday, July 22 through Saturday, July 25 | 7:30 PM to 10:00 PM | The Naples Players

These are the full theater-night performances to build around. If you want the week to feel like more than dinner out, this is still the strongest bet in town.

Info: https://www.visitnaplesfl.com/event/les-miserables/2026/07/22

Sunday, July 26 | 2:00 PM to 4:30 PM | The Naples Players

The Sunday matinee is the comfortable multigenerational choice. It avoids a late night, keeps dinner flexible, and still gives the weekend a real cultural anchor.

Info: https://www.visitnaplesfl.com/event/les-miserables-matinee/2026/07/26

Tuesday, July 28 | 3:30 PM to 5:30 PM | Empowerment Farm

A gentle weekday pick for families, visiting grandchildren, or anyone who wants something slower and different. Keep expectations simple: animals, a calm pace, and an early finish.

Info: https://www.visitnaplesfl.com/event/tuesday-night-tuck-in-on-the-farm/2026/07/28

Wednesday, July 22, Sunday, July 26, and Wednesday, July 29 | 12:00 PM to 3:00 PM | Paradise Food Tours

This remains one of the easiest visitor plans in Naples. You get the walk, the tastings, and the Fifth Avenue story without having to negotiate where lunch should be.

Pair it with Les Miserables if you want a full downtown day, or use it as the structured piece of a lighter itinerary.

Info: https://www.visitnaplesfl.com/event/feast-on-5th-naples-food-tour/2026/07/22

Wednesday, July 22 and Wednesday, July 29 | 5:00 PM to 8:00 PM | Rooftop at Riverside

A social, casual early-evening option with a pet-friendly hook. It is best as a relaxed meet-up before dinner, especially for readers already heading toward Bonita Springs.

Info: https://www.visitnaplesfl.com/event/wooftop-wednesday-at-rooftop/2026/07/22

Saturday, July 25 | 11:30 AM to 4:00 PM | Sails Restaurant

This is the polished brunch lane. Use it when the meal should be the plan, especially for birthdays, visitors, or a weekend that needs a little ceremony.

Info: https://www.visitnaplesfl.com/event/saturday-champagne-brunch/2026/07/25

Sunday, July 26 | 11:30 AM to 4:00 PM | Sails Restaurant

The Sunday version gives you the same elevated brunch plan with more breathing room around Saturday schedules. It pairs neatly with an easy afternoon or a quiet evening at home.

Info: https://www.visitnaplesfl.com/event/sunday-champagne-brunch/2026/07/26

Saturday, July 25 and Sunday, July 26 | 11:00 AM to 3:00 PM | Taberna Burntwood

A practical brunch choice when you want something easier to schedule before a matinee, a water outing, or a relaxed afternoon.

Info: https://www.visitnaplesfl.com/event/weekend-brunch-at-taberna/2026/07/25

Sunday, July 26 | 10:00 AM to 2:00 PM | Tigress Restaurant & Rooftop Bar

Use this as the more playful Sunday brunch pick. It is better when you want the meal to carry the plan, not just fill the slot before the plan.

Info: https://www.visitnaplesfl.com/event/brunch-with-a-roar-at-tigress-restaurant-rooftop-bar/2026/07/26

Wednesday, July 29 | 6:00 PM to 9:00 PM | The Baker Museum at Artis-Naples

This is the sharpest arts note just beyond the weekend. Admission is free, with museum exhibitions, concessions, and live music by Jerry Stawski on keyboard, which makes it a low-pressure way to make an ordinary Wednesday feel more intentional.

Info: https://artisnaples.org/events/art-after-hours.2627.1

Thursday, July 23 | 10:00 AM to 11:00 AM | Historic McSwain Home Museum and Gardens

The Thursday morning slot is the better summer version of this tour. It is a small history-and-walking plan, best for readers willing to go a little north and keep the rest of the day light.

Info: https://www.visitnaplesfl.com/event/the-downtown-bonita-springs-walking-history-tour-2/2026/07/23

Friday, July 24 through Sunday, July 26 | 8:00 AM to 4:00 PM | Flamingo Island Flea Market

Casual weekend browsing rather than a marquee cultural event, but it can scratch the treasure-hunt itch if you go early and keep it easy.

Info: https://www.visitnaplesfl.com/event/flamingo-island-flea-market/2026/07/24

Wednesday, July 22 and Wednesday, July 29 | 7:00 PM to 9:00 PM | Rooftop at Riverside

Light, social, and easy to pair with an early drink or dinner. Best for readers who want something playful without turning the night into a production.

Info: https://www.visitnaplesfl.com/event/twisted-bingo-at-rooftop/2026/07/22

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

Still one of the easiest ways to make a quiet summer week feel like Naples. Good for visiting family, low-planning afternoons, and a water-view outing that does not require towels, chairs, or a full beach setup.

Info: https://www.visitnaplesfl.com/event/naples-princess-cruises/2026/07/22

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

A flexible Tin City-adjacent option when you want the water without overbuilding the day. Pair it with lunch nearby and keep the rest of the schedule simple.

Info: https://www.visitnaplesfl.com/event/pure-florida-daily-sightseeing-excursions/2026/07/22

Daily | 9:00 AM to 6:00 PM | Naples Electric Bikes

This belongs in the summer visitor toolkit, but make it a morning plan. Keep the route simple and do not pretend a July afternoon ride is the comfortable version.

Info: https://www.visitnaplesfl.com/event/daily-e-bike-rentals/2026/07/22

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

There is not a strong in-town sports event this weekend, so this is a calendar note rather than a this-week outing. FC Naples returns home August 5 against AV ALTA FC, which gives local sports readers a clean night to circle.

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

Friday, October 23 | 7:30 PM | Hertz Arena

Too far out for the weekend calendar, but worth knowing for hockey readers who plan early. The Everblades return to Hertz Arena in October.

Info: https://www.floridaeverblades.com/

Daily | Naples Botanical Garden

Still a reliable family and visitor stop if you go early, dress for heat, and keep the pace easy. Use it as a morning anchor, then move lunch indoors.

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

Daily | Corkscrew Swamp Sanctuary

A quieter nature choice for readers who want shade, boardwalks, and a slower morning. Check current hours before driving out.

Info: https://corkscrew.audubon.org/

Daily | 9:00 AM to 6:00 PM | Naples Electric Bikes

Useful for visitors who want to see more of town without turning the day into a beach setup. Morning is the whole point here.

Info: https://www.visitnaplesfl.com/event/daily-e-bike-rentals/2026/07/22