A Local Guide to What’s Happening in Naples, Bonita Springs, Fort Myers, Cape Coral, and Sanibel & Captiva
January is one of the most exciting months of the year in Southwest Florida. With ideal weather, seasonal residents back in town, and a packed cultural calendar, the region comes alive with nationally recognized art festivals, food events, and community celebrations. Here’s what’s happening across the communities you listed.
Naples & Olde Naples
Naples New Year’s Art Fair – January 3–4, 2026
Celebrating its 30th edition, this prestigious fine art fair is organized by the Naples Art Institute and ranks among the top juried art festivals in the United States. Artists from across the country showcase museum-quality pieces in a beautiful outdoor setting, attracting collectors, designers, and art lovers from all over.
29th Annual Art Festival at Fleischmann Park – January 17–18, 2026
This popular annual event, operated through the Naples Art Institute, transforms Fleischmann Park into a vibrant open-air gallery. Guests can browse original artwork, meet artists, and enjoy a relaxed community atmosphere.
The World-Famous Swamp Buggy Races – January 18, 2026
A true Southwest Florida tradition. The 77th Annual Swamp Buggy Parade begins at Coastland Center Mall (US-41 & Fleischmann Blvd) and travels south along Tamiami Trail to 5th Avenue South. This iconic event celebrates local heritage with floats, crowds, and festival energy throughout Naples.
Naples Winter Wine Festival – January 30 – February 1, 2026
One of the most prestigious charity wine events in the world. Proceeds benefit the Naples Children Foundation, whose mission is to improve the lives of underprivileged and at-risk children throughout Collier County. The weekend draws international attention to Naples.
Art in the Park – January 31, 2026
Part of the Naples Art Institute’s long-running “Art in the Park” series, this annual event offers another opportunity to experience high-quality art in a relaxed outdoor setting.
Bonita Springs & Estero
Bonita Springs National Art Festival – January 10–11, 2026
Held at scenic Riverside Park in downtown Bonita Springs, this nationally recognized juried art festival attracts thousands of visitors and serious art buyers. The event showcases fine art, craftsmanship, and a strong community atmosphere along the Imperial River.
Wonder Gardens – 90th Celebration – January 31, 2026
This special anniversary celebration includes curated food from local restaurants, live entertainment, animal encounters, a Fund the Future paddle raise, mystery auction items, and a wine pull — hosted by Peter Busch. A unique and elegant community event in Bonita Springs.
Fort Myers
Caloosahatchee Celtic Festival – January 24–25, 2026
Presented by McGregor’s Public House, this annual festival invites guests to don their kilts and enjoy a full weekend of Celtic culture. Expect live music, traditional performances, themed food, vendors, and a strong local following.
Fort Myers Seafood & Music Festival – January 30 – February 1, 2026
A crowd favorite featuring fresh seafood prepared onsite, live music throughout the weekend, and a wide variety of food options including meat, vegetarian dishes, and desserts. The seafood highlights Florida’s coastal waters and regional flavors.
Cape Coral
41st Annual Cape Coral Art Festival – January 10–11, 2026
Now in its 41st year, this long-standing festival continues to grow each year. Visitors can enjoy a diverse collection of artwork, local food vendors, and an energetic atmosphere in the heart of Cape Coral.
Tour de Cape – January 23–25, 2026
A multi-day cycling event featuring:
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A 5K race
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Mini Kids Ride
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15, 30, 62, and 100-mile cycling routes
Riders experience scenic routes throughout northwest and southwest Cape Coral, drawing participants from across the region.
Sanibel & Captiva Islands
Taste of the Islands – January 10–11, 2026
A beloved island tradition celebrating the culinary scene of Sanibel and Captiva. Guests can sample dishes from local restaurants while enjoying live entertainment and a festive island atmosphere.
