Grumpy Old Men: The Musical
From 1/8/2026 - 1/18/2026
Grumpy Old Men: The Musical is a hilarious adaptation of the 1993 film, complete with witty one-liners and a cheerful musical score. The storyline revolves around Max and John, two quarreling neighbors whose lifelong feud forms the heart of this entertaining spectacle.
Barron Collier Companies Naples Half Marathon
On 1/18/2026
Run Naples offers an exhilarating experience, with the opportunity to share the course with professional runners and Olympic hopefuls. The event promises a comfortable average morning temperature of 56 degrees, free race photos, post-race celebrations with food, music, and camaraderie, unique medals for all finishers, and awards for various age groups.
Pets on Third Pet Parade and PetFest
On 1/18/2026
This pet-friendly event invites all well-behaved animals to participate in a parade and costume contest, with a special theme celebrating 250 years of American history. Attendees can expect a bustling atmosphere filled with vendors and services dedicated to pet health and well-being, as well as prizes for the best-dressed, most creative, and most colonial-themed pet and owner pairs.
Naples Boat Show
From 1/22/2026 - 1/25/2026
The Naples Boat Show stands as the most significant recreational exhibition in the Naples-Marco Island area. Attendees can expect a variety of displays from marinas, boat dealers, and a myriad of other businesses related to the marine industries.
Paint and Sip
On 1/11/2026
Anticipate tapping into your artistic skills at an engaging paint-and-sip event, birthed in an alcohol-free ambiance. Feel the indulgence of a beautiful variety of tea mocktails, kava, and elixirs at this universally skill-appropriate and positively vibrant gathering.
Beau Jest
From 1/14/2026 - 2/15/2026
Beau Jest, a heartwarming comedy, revolves around Sarah, a young woman who employs an actor to impersonate her ideal boyfriend, aiming to appease her conservative parents. The plot thickens as the pretense hilariously unravels, unveiling secrets, opening hearts, and delivering more than expected in this touching narrative about love, identity, and family.
& Juliet (Touring)
On 1/27/2026
& Juliet is a high-energy jukebox musical that reimagines Shakespeare’s Romeo and Juliet with a feminist twist, asking: What if Juliet didn’t die? Featuring hit pop songs from legendary songwriter Max Martin, the show blends humor, heart, and empowerment in a modern retelling. The touring production brings this electrifying Broadway favorite to cities across the country.
Swamp Buggy Parade
On 1/17/2026
Get ready for a beloved tradition, the annual Swamp Buggy Parade, promising a day filled with laughter and hometown pride. The theme this year is 77 years of Swamp Buggies, Sunshine and Speed, and attendees are encouraged to bring friends, family, and plenty of community spirit to make this parade one to remember.
Naples Winter Wine Festival
From 1/30/2026 - 2/1/2026
Indulge in a lavish weekend of fine wines and gourmet cuisine at the prestigious Naples Winter Wine Festival. Held annually in the stunning Naples, Florida, this charitable event attracts high-profile attendees and showcases world-class vintages through exclusive tastings and auctions. With a lineup of renowned chefs and live entertainment, this opulent gathering promises an unforgettable experience for the most discerning oenophiles.
Doll Show and Sale
On 1/31/2026
This annual event is a collector's paradise, showcasing a wide array of antique, vintage, and modern dolls, teddy bears, miniatures, toys, doll clothes, and accessories. Attendees can look forward to door prizes, raffles, a silent auction, and even services like identification/valuation, restringing, and minor repair, all in a handicap accessible environment.
