Naples
Naples, Florida, embodies the essence of coastal charm and luxury on the Gulf of Mexico. Renowned for its stunning beaches and pristine waters, Naples offers visitors a quintessential Florida experience. The city’s Naples Pier is a local landmark and a must-visit spot for panoramic views, fishing, and beautiful sunsets. Whether you’re strolling along the pier or relaxing on the sandy shores, the scenic beauty of Naples is sure to captivate.
For those interested in nature and wildlife, the Corkscrew Swamp Sanctuary provides a glimpse into Florida’s unique ecosystem. This protected area features a boardwalk that winds through a lush cypress swamp, offering opportunities to see diverse wildlife such as alligators, birds, and turtles. The sanctuary’s diverse habitats make it a haven for nature enthusiasts and photographers alike.
Naples is known for its high concentration of millionaires and boasts some of the highest real estate values in the country. This affluence is reflected in the city’s luxurious amenities, including upscale shopping at The Waterside Shops, fine dining, and exclusive golf courses.
For those interested in nature and wildlife, the Corkscrew Swamp Sanctuary provides a glimpse into Florida’s unique ecosystem. This protected area features a boardwalk that winds through a lush cypress swamp, offering opportunities to see diverse wildlife such as alligators, birds, and turtles. The sanctuary’s diverse habitats make it a haven for nature enthusiasts and photographers alike.
Naples is known for its high concentration of millionaires and boasts some of the highest real estate values in the country. This affluence is reflected in the city’s luxurious amenities, including upscale shopping at The Waterside Shops, fine dining, and exclusive golf courses.
Learn More About Naples
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.
The Curious Incident of the Dog in the Night-Time
From 2/4/2026 - 3/1/2026
Immerse yourself in the captivating narrative of The Curious Incident of the Dog in the Night-Time, a highly praised play adapted from Mark Haddon's popular novel. With a mix of emotion, comedy, and impressive visuals, this uplifting tale allows attendees to perceive the world through the lens of a gifted teenager overcoming obstacles, embracing his individuality, and uncovering his remarkable capabilities.
Gutenberg: The Musical
From 2/5/2026 - 2/15/2026
Gutenberg: The Musical is a Tony-nominated, comedic two-man show that follows the journey of Bud and Doug, aspiring theatre writers and composers, as they pitch a hilariously inaccurate musical about Johannes Gutenberg to potential investors. The duo, armed with basic research and boundless ambition, sing all the songs, play every role, and narratively guide the audience through their chaotic yet endearing performance, hoping to secure funding for their self-proclaimed masterpiece.
Bonita Springs Seafood and Music Festival
From 2/6/2026 - 2/8/2026
The Bonita Springs Seafood and Music Festival is an event that celebrates delicious seafood, live music, and a fun community atmosphere. Typically held in Bonita Springs, Florida, this festival features a wide array of seafood dishes prepared by local restaurants and food vendors. Attendees can enjoy a variety of culinary delights, listen to live musical performances spanning different genres, and experience the local culture. The festival provides a great opportunity for locals and visitors alike to gather, enjoy good food, and be entertained. If you're planning to attend, be sure to check the event’s schedule for specific dates, musical acts, and any special activities or attractions.
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