While much of the country bundles up, Florida’s Gulf Coast comes alive with sunshine and celebration. Winter here means festival season — and there’s something happening almost every weekend.
Here’s a snapshot of just some of the Greater Sarasota area's upcoming events to start your Florida Gulf Coast winter season planning.
For the art and outdoor festival lovers: Stroll through streets lined with colorful creations at the St. Armands Circle Winter Art Festival & Sidewalk Sale and the Downtown Sarasota Festival of the Arts, where local, regional, and international artists showcase everything from paintings and sculptures to jewelry and photography.
Lights in Bloom(R)
- December 5, 2025 - January 3, 2026
- Marie Selby Botanical Gardens | Downtown Sarasota Campus
St. Armands Circle Winter Art Festival & Sidewalk Sale
- Saturday & Sunday | January 24-25, 2026 | 10:00am to 5:00pm
- 1 St. Armands Circle in Sarasota, FL | Free Admission
Downtown Sarasota Festival of the Arts
- Saturday & Sunday | February 7-8, 2026 | 10:00 am to 5:00 pm
- 1718 Main Street in Sarasota, FL | Free Admission
For the indie spirits: Discover the unexpected at the Atomic Holiday Bazaar, a lively market full of handmade and offbeat finds from creative makers. Or, explore the Downtown Sarasota Fine Art and Craft Fair for beautiful, one-of-a-kind pieces that make perfect gifts or keepsakes.
- Saturday & Sunday | December 6-7, 2026
4th Annual Downtown Sarasota Fine Art and Craft Fair
- Saturday & Sunday | March 14-15, 2026 | 10:00 am to 5:00 pm
- 1718 Main Street in Sarasota, FL
For the culture seekers: The Winter Opera Festival, hosted by the renowned Sarasota Opera, brings both well-known classics and rarely performed gems to life in a way only Sarasota can through a series of events. Learn more here.
For the thrill seekers:
Rev your engines at Thunder by the Bay, where motorcycles, live music, and high-energy entertainment fill the Sarasota Fairgrounds.
- Friday - Sunday | February 12-15, 2026 | 3000 Ringling Blvd. , Sarasota, FL
And for a taste of tradition: Don’t miss the Sarasota Highland Games & Celtic Festival, a celebration of athletic competition, bagpipes, and authentic Celtic fare that will make you feel like you’ve traveled straight to Scotland.
- Saturday | January 31, 2026 | Sarasota Fairgrounds
From art walks to bagpipes, Sarasota’s winter festival season is full of warmth, color, and community — proving that in paradise, winter doesn’t mean slowing down.
Source: Visit Sarasota; Thunder by the Bay, Lights in Bloom, and Sarasota Opera House images courtesy of Visit Sarasota.