From art festivals to seaside fairs and wildlife celebrations — January in Southwest Florida brings sunshine, community events, and fun for all ages. Whether you’re planning family outings, weekend plans, or showcasing local culture to visitors and clients, here are the can’t-miss happenings.
Naples & Olde Naples
• Naples New Year's Art Fair January 3 & 4, 2026
This is the 30th edition of this major annual art fair organized by the Naples Art Institute. This art show ranks amongst the top fine art fair in the USA and attracts artists from around the country.
• 29th Annual Art Festival in Fleischmann Park January 17 & 18, 2026
The Naples Art Institute building is the operational hub for Art in the Park. Art in the Park will be held at Fleischmann Park
• The World Famous Swamp Buggy Races January 18, 2026
The 77th Annual Swamp Buggy Parade will begin at the Coastland Center Mall located at US 41 and Fleischmann Blvd. and will continue south on Tamiami Trail to 5th Ave. S
• Naples Winter Wine Festival January 30 - February 1, 2026
Proceeds from the Festival benefit the Naples Children Foundation (NCF), whose vision is to make a profound and sustaining difference in the quality of children’s lives.
• Art in the Park January 31
Naples Art Institute's long-standing annual "Art in the Park" series of art fairs continues in the 2025-2026 season.
Bonita Springs & Estero
• Bonita Springs National Art Festival January 10 & 11, 2026
Held at scenic Riverside Park in downtown Bonita Springs, Florida, this juried event draws thousands of passionate art lovers and buyers from across the region.
• Wonder Gardens – 90th Celebration January 31, 2026
Enjoy sumptuous bites from local restaurants, live entertainment, animal encounters, our Fund the Future Paddle Raise, mystery auction items, and a special wine pull– hosted by Peter Busch.
Fort Myers
• Caloosahatchee Celtic Festival January 24 & 25, 2026
Get ready to don your kilts for the much-anticipated 2026 Caloosahatchee Celtic Festival, presented by McGregor's Public House
• Fort Myers Seafood & Music Festival January 30 - February 1, 2026
Enjoy foods cooked fresh onsite (seafood, meat, vegetarian) with a variety of side dishes and of course – desserts! Seafood is from Florida’s coastal waters
Cape Coral
• 41st Annual Cape Coral Art Festival January 10 & 11, 2026
This year’s festival promises to be even more exciting than ever before, with a diverse array of artwork, delicious food, and much more.
• Tour de Cape January 23 - 25, 2026
The event includes a 5K, a Mini Kids Ride, and 15-30-62-100 mile bike tours in the northwest and southwest regions of Cape Coral.
Sanibel & Captiva Island
• Taste of the Islands January 10 & 11, 2026
This year’s festival promises to be even more exciting than ever before, with a diverse array of artwork, delicious food, and much more.
__________
January is also prime time for outdoor living in SWFL — warm weather and scenic bliss mean:
- Beach yoga and sunrise fitness around Naples, Bonita Springs and Fort Myers Beach
- Farmers markets, live music nights and “Sip & Shop” events throughout Lee & Collier counties
- Nature hikes, kayaking and wildlife tours at local parks like Lovers Key State Park and Estero Bay Preserve State Park
Check local event calendars such as Visit Naples Events, ParadiseCoast.com Events, and Visit Fort Myers Events for the most up-to-date January listings.
Wrap-Up: Why January in SWFL Is Awesome
January in Southwest Florida offers a perfect blend of arts, culture, nature, and beachside living — ideal for locals, snowbirds, and visitors alike. From major art festivals and birding adventures to weekly markets and world-class theater, you’ve got options for every interest and pace.
Bonus Tip: Because this region is such a draw in winter, many ticketed events and art fairs sell out early — plan ahead!
Socials