Your Naples Week Ahead: Jet-Set or Chill — SWFL Events Sept 10–17

A Quick Sip Before the Week

September in Naples means that summer’s heat is still here, but the calendar is filling with cool ways to spend your time. Whether you’re up for live music, outdoor adventures, family fun, or just a breezy brunch with friends, this week has plenty of options to keep you moving (or relaxing). Here’s your curated list of things to do from September 10 through 17.

This Week’s Highlights

Wednesday, Sept 10

• Beach Yoga at Vanderbilt Beach (9 – 10 a.m.) — Stretch into midweek with sun, sand, and deep breaths.

• Wooftop Wednesday at Rooftop at Riverside (5 – 8 p.m.) — A dog-friendly happy hour for you and your pup.

Friday, Sept 12

• Tom Shillue Live (6:45 p.m.) — Nationally known comedian brings sharp wit and laughs to Naples.

Weekend Vibes – Sat 13 & Sun 14

• Princess Tea Party on the Naples Princess (Sat 3 – 4:30 p.m.) — Fairy-tale fun on the water for kids and families.

• Weekend Brunch at Mercato (Sat & Sun 11 a.m.–3 p.m.) — Classic favorites with modern flair.

• Bark on the Ark (Keewaydin Island) (Sat 8 – 11 a.m.) — Bring your pup aboard for a boat ride and sandy adventure.

• Vanderbilt Farmer’s Market (Sun 8 a.m.–1 p.m.) — Fresh produce, local vendors, and relaxed Sunday energy.

Midweek/Weekend Extras

• Disney on Ice “Jump In!” (through Sept 14 at Hertz Arena) — Magical skating and storytelling for all ages.

• Art After Hours at The Baker Museum (Sept 24, save the date) — Free evening gallery access.

• Evening on Fifth (Sept 11) — Live music, open-air dining, and local flair along Fifth Avenue.

• Outdoor Movie: “Lilo & Stitch” at Mercato (Sept 16) — Popcorn and Disney classics under the stars.

• Naples Art Institute Invitational Show (running through Nov 30) — Inspiring pieces from local and regional artists.

Explore the Outdoors

Looking for a nature reset? The Corkscrew Swamp Sanctuary offers a serene 2.25-mile boardwalk through towering cypress trees and abundant wildlife. Or make it a day-trip north to Bonita Springs, where you can kayak to Mound Key, stroll Wonder Gardens, or dig through treasures at Flamingo Island Flea Market.

Weekly Planner