Friends and neighbors,
Naples is coming alive this week. Evening on Fifth fills downtown with live music tonight, while Hopsized has started pairing Thursday-night Pilates with a post-class beer. This weekend, Naples Beach Club is giving us an early look at the sports pub The Wager during both US Open finals, and Wine Around the Water returns Saturday with tastings around Venetian Village benefiting SNIP Collier.
Looking to next week, I found two worth getting on the calendar now: a rather unconventional cake-decorating night at Nat Nat and a 25-seat Thai dinner at Tong Yin.
Hope you find something to put on the calendar!
Warmly,

Table of Contents
Top 6 Events This Week: Cake with Wine, Pilates with Beer, and a Sneak Peek of The Wager

1. Evening on Fifth
📅 Thursday, September 10 | 6:30–9 PM
📍 Fifth Avenue South | Downtown Naples
Evening on Fifth returns Thursday, with live musicians set up along the sidewalks of Fifth Avenue South from 6:30–9 PM. There’s no central stage or ticket required; the performances are spread along the avenue, so this is an easy evening plan to combine with dinner or drinks downtown. Details.

2. Pilates After Hours at Hopsized
📅 Thursday, September 10 | Every Thursday
📍 Hopsized Brewing Company | 9201 Cockleshell Court, Unit 13, Bonita Springs
Hopsized and Fit & Flow Pilates have started a Thursday-night Pilates series, with a 45-minute mat class followed by a drink in the taproom. Mats and props are provided, the class is beginner-friendly, and your ticket includes one beer, sangria, hard seltzer or nonalcoholic drink afterward. This isn’t a one-off: Pilates After Hours is scheduled every Thursday, so if this week doesn’t work, there’s another chance next week. Tickets.

3. US Open Finals at The Wager
📅 Saturday–Sunday, September 12–13 | Women’s Final Saturday; Men’s Final Sunday
📍 Naples Beach Club, A Four Seasons Resort | 801 Gulf Shore Blvd. N., Naples
The Wager doesn’t officially open until October, but Naples Beach Club is giving locals an early look this weekend with pop-ups for both US Open tennis finals. There’s a specially curated à la carte menu, plus access to the new game area with arcade and table games during breaks in play. The four-lane bowling alley will also be available for an additional charge, subject to availability. Reservations are just $1 per person and can be made for groups of up to eight. Reservations.

4. Wine Around the Water
📅 Saturday, September 12 | 5–7 PM
📍 The Village Shops on Venetian Bay | 4200 Gulf Shore Blvd. N., Naples
Wine Around the Water returns to the Village Shops Saturday evening, with a $30 ticket covering a commemorative wine glass, tasting passport and wine samples at stops around the center, plus discounts at participating restaurants. One hundred percent of ticket proceeds benefit SNIP Collier and its work providing affordable spay and neuter services, vaccines and preventative care for local dogs and cats. Registration is on both sides of the Village, in front of Everything But Water and T-Michaels Steak & Lobster. Tickets and details.

5. Chaos Cake Decorating at Nat Nat
📅 Tuesday, September 15 | 6–9 PM
📍 Nat Nat | 3080 Tamiami Trail N., Suite 1, Naples
Bicyclette Pastry Chef Corie is taking over Nat Nat for a three-hour cake-decorating class where everyone gets a two- or three-layer cake to construct and decorate themselves. Corie will teach the fundamentals of cake construction along the way, and snacks, wine and nonalcoholic drinks are included. You leave with the cake you made. Tickets.

6. Beauty From the Inside Out at Tong Yin
📅 Thursday, September 17 | 5:30–8:30 PM
📍 Tong Yin on 9th | 75 9th St. S., Naples
Tong Yin is teaming up with GBY Skincare Health + Wellness for a dinner limited to just 25 guests, all seated together at one long table. The menu includes Miang Kham, Tom Kha soup, pomelo salad, live Som Tam preparation, glass-noodle Pad Thai with grilled prawn, tableside crab curry and coconut dessert, with some dishes demonstrated or finished in front of the group. The ticket also includes a welcome drink, live violin music, a goodie bag and your choice of a $50 Tong Yin or GBY gift card. Tickets.
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Start with a swim in the heated waterfall pool. Grill dinner while the dog runs around the huge fenced yard. Pick a mango from the tree if one is ready. Then end the night around the fire pit instead of figuring out where to go next.
Why It Works
💦 Heated waterfall pool
🔥 Fire pit
🥭 Mango trees + oversized fenced yard
🐾 Pet-friendly
🛏️ 4 bedrooms
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And when you do want to head out, the beach and Fifth Avenue South are close by.
This is the kind of Naples rental that does not just give you a place to stay. It gives you another part of the trip to look forward to.
Poll Results: Long weekends?
Last week we asked: What are you most likely to make time for over a three-day weekend?
Here’s where you landed:

Apparently, the ideal long weekend is split evenly between enjoying the outdoors or refusing to leave the house entirely. Beach, boating or something outdoors tied with staying home at 21% each, while going out for a special meal was barely behind at 20%. The loser? A quick getaway. There’s no need to sit in traffic when you live where everyone else is trying to go!
This Week’s Poll: Party of…?
Who are you usually making plans for?
Why It Matters
This is one of those weeks that makes Naples easy to say yes to. You can wander Fifth Avenue with live music in the background, try Pilates with a beer afterward, sneak into The Wager before its official opening, or spend Saturday evening sipping your way around Venetian Village.
And if none of that fits, next week already has cake decorating and a very intimate Thai dinner waiting. However you spend it, I hope you find one good reason to get out of the house and enjoy the city a little differently.
Warmly,

Elizabeth Bellotti
Editor-In-Chief
Naples, Florida
The Naples Florida Review
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