Friends and neighbors,
Costume or not, Naples has no shortage of ways to celebrate this Friday night. At the end of this newsletter is a quick list of all the Halloween happenings I’ve found around town.
But beyond Friday, Artis—Naples brings both mystery and laughter with illusionist Chris Funk and the ever-hilarious David Sedaris. And for theater lovers, Gulfshore Playhouse continues performances of a sharp-tongued classic, while Marco Island’s art center debuts a lighthearted romantic comedy to balance things out.
Grab your costume or just go for the people-watching. Either way, I hope you have a wonderful weekend and stumble upon something you love.
Happy Halloween,
If you have a tip or event to share, email me at [email protected] — I’d love to feature your favorite finds!
Top 6 Events This Week: Magical Tricks & Theatrical Treats
1. Halloween Night Evening on 5th
📅 Friday, October 31 | 6:30 – 9:30 PM
📍5th Ave South, Naples
Stroll 5th Ave. as it transforms into a Halloween block party of live music, art, face painting, and more. Sure to be a top people-watching evening. Event info.
2. Chris Funk Musical Illusionist at Artis—Naples
📅 Sunday, November 2 | 5:00 PM & 7:30 PM Performances
📍Artis—Naples, 5833 Pelican Bay Blvd, Naples
Chris Funk lives up to his name, delivering an unusual mix of jaw-dropping magic with live music in a one-of-a-kind multimedia performance. He fuses live music and mind-bending tricks in a show that’ll make you question your reality (and your eyes). Think levitating violins. As seen on America's Got Talent. Tickets are $66-67.
3. Evening with David Sedaris at Artis—Naples
📅 Sunday, November 2 | 7:00 PM
📍Artis—Naples, 5833 Pelican Bay Blvd, Naples
The king of dry wit and self-deprecating charm is back following the release of Happy Go Lucky and his first children’s book, Pretty Ugly. Expect readings from recent and unpublished work, a candid Q&A and a post-show book signing from one of America’s most amusing storytellers. Tickets are $65-80
4. Deep Blue Debut
📅 Wednesday, November 5 | 6:00 – 9:00 PM
📍Mercato, 9110 Strada Pl, Naples
Celebrate the unveiling of Mercato’s new Piazza. Snack on tastes from 10 Mercato restaurants, grab coastal-inspired drinks at their open bar, and experience one-of-a-kind entertainment and photo ops. Live music from Miami party band Extasy. Blue hues encouraged, proceeds benefit Guadalupe Center. After-party at Beeline and mermaid sightings are possible. Tickets are $125 per person (or bring a date for $200).
5. Baggage @ The Marco Island Art Center
📅 Thursday, November 6 - 23 | 7:30 PM Wed - Sat, 3:00 PM Sat & Sun
📍1089 N Collier Blvd Suite #432, Marco Island
The Marco Island Art Center begins its on-stage season with playwright Sam Bobrick’s romantic comedy Baggage. Two strangers swap luggage and unpack emotional baggage, love, and second chances. Heartful and amusing. Tickets are $40.
6. Who’s Afraid of Virginia Woolf? @ Gulfshore Playhouse
📅 Through November 23 | 7:30 PM Wed-Sat, Weekend Matinees
📍100 Goodlette-Frank Rd, Naples
Gulfshore opens their season with Edward Albee’s brilliant masterpiece. What begins as a polite nightcap between two couples spirals into a razor-sharp game of truth and illusion. Piercing and darkly humorous lines make for an unforgettable night. Tickets start at $39.
Presented by Naples Florida Rentals: Golf-Front 3BR Oasis with Private Heated Pool, Spa & Lanai 🌴
Sunrise on the fairway. Stars over your private, heated pool. Guests call it “a resort without the crowds.”
Bookable right now (Oct 30):
Sleeps the crew: king, queen, bunk room, crib + pack-and-play
Cook for real: full kitchen, family-ready dinnerware
Indoor–outdoor flow: screened lanai, loungers, fenced yard, pets welcome
Minutes to beaches, great restaurants, and boutique shopping
Last October slots are disappearing; early November is opening up.
From $179–$249/night.
Halloween Around Town
Friday October 31st
🎭 Vergina – Roman Empire Party
Costume contest 10 PM, tarot readings, live music all night.
🌊 Blue Martini – Into the Deep Blue
Starts 4 PM | DJ Rifik & Remix Band, costume contests, bottle specials.
🍸 The Hampton Social – Happy Hour Party
3–6 PM | $100 gift card costume contest, festive cocktails.
🎧 The Mini Bar – Halloween Party
7 PM–12 AM | DJ Apollo, costume contest 9 PM, no cover.
🍻 The Pub – Halloween Party
9 PM | DJ 007, $500 in costume contest prizes, drink specials.
🦜 The Real Macaw – Spooky Soirée
5–8 PM | Live band, costume prizes, witchy cocktails, no cover.
☕🎶 Bayshore Bodega – Halloween Coffee Rave
6–9 PM | DJ Unek by the waterfront, costume prizes, coffee cocktails, family-friendly.
Poll Results: Preseason Priorities
The resounding winner was Try new spots before you can’t get a reservation and I can’t argue with that one. Many new restaurants will be opening in the coming weeks, and it’ll be wise to get in early before the rush!
This Week’s Poll: Live theater?
As a theater lover, I always like to feature new shows around town. But I’m curious about my audience, so tell me:
When’s the last time you saw live theater?
Why It Matters
Costumes, curtain calls, and plenty to explore. If you head out, hit reply with a photo or a quick note about your favorite stop, and we’ll share a few next issue.
Don’t forget to vote in this week’s poll and send tips or openings our way.
Until then, enjoy the cool evenings, support local, and have a safe, happy Halloween.
Elizabeth Bellotti
Editor-In-Chief
Naples, Florida
The Naples Florida Review
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