Sarasota Winter Events Calendar: November 2026 to April 2027

Planning a winter trip and want to know what's on? This Sarasota winter events calendar covers November 2026 through April 2027, month by month: art festivals, holiday nights, sand sculpting, the opera season and Orioles spring training. Every date below was checked against the organizer's or the city's own page in mid-October 2026. When a date hadn't been posted yet, we say when the event usually happens and where to check. For the bigger events, we link to our full guide.

Sarasota Winter Events at a Glance

• Nov. 13 to 16: Siesta Key Crystal Classic sand sculpting festival on Siesta Beach.
• Nov. 14 to 15: St. Armands Circle Art Festival.
• Dec. 4: Holiday Night of Lights and the tree lighting on St. Armands Circle.
• Jan. 24: Forks & Corks Grand Tasting at The Ringling.
• Feb. 13 to 14: Downtown Festival of the Arts on Main Street.
• Feb. 19 to March 19: Orioles spring training home games at Ed Smith Stadium.
• March 28: Easter Sunday.
• Busiest stretch: February through early April. Book flights, rooms and weekend dinners early.

November 2026

November is when the season wakes up. The weather turns dry and mild, and the event calendar fills fast.

• Saturday, Nov. 7, 9 a.m. to 3 p.m.: Ferraris on the Circle, a car show on St. Armands Circle.
• Weekends from Nov. 7 to Dec. 6: the Sarasota Medieval Fair, Saturdays and Sundays from 9:45 a.m. to 5:30 p.m. at Mallaranny Farms in Myakka City, inland from town. It runs rain or shine.
• Nov. 8 to 15: the Living Arts Festival, a week of theater, music, dance, circus and visual art at venues around the region, with some free events and some ticketed. See our Living Arts Festival guide.
• Nov. 13 to 16: the Siesta Key Crystal Classic, an international sand sculpting festival on Siesta Beach. Our Crystal Classic guide covers tickets and parking.
• Nov. 14 to 15, 10 a.m. to 5 p.m.: the 37th annual St. Armands Circle Art Festival, with artists set up around the Circle.
• Chalk festival: the Sarasota Chalk Festival has traditionally taken over Burns Square downtown in November, but 2026 dates weren't posted when we checked. Read our Chalk Festival guide and check chalkfestival.org.
• Thanksgiving, Nov. 26: the long weekend runs Nov. 26 to 29. The Ringling is closed on Thanksgiving Day. Our Thanksgiving guide has the rest.

December 2026

• Friday, Dec. 4, 5:30 to 8 p.m.: the 48th annual Holiday Night of Lights on St. Armands Circle. It's free, and the 60-foot tree in the center park lights up for the season. Book dinner nearby ahead of time.
• Saturday, Dec. 5: the downtown Holiday Parade on Main Street. Organizers hold it on the first Saturday of December. The start time hadn't been posted, so check the city's events calendar.
• Saturday, Dec. 12, 9 a.m. to 2 p.m.: Porsches in the Park on St. Armands Circle.
• Holiday Boat Parade of Lights: usually a Saturday in mid-December on the bay, best seen from Bayfront Park and Marina Jack. Check the official listing for 2026.
• Christmas and New Year's: The Ringling is closed on Christmas Day and New Year's Day, and the week between them is one of the busiest of the year.

For holiday lights, The Nutcracker and New Year's Eve, see our guide to things to do in December.

January 2027

• Jan. 2 to 3: Longboat Key Festival of the Arts.
• Early January: a winter fine art festival is usually held at J.D. Hamel Park on the downtown bayfront the first weekend of the year. Check the city's events directory for 2027.
• MLK weekend, Jan. 16 to 18: Westcoast Black Theatre Troupe's annual Celebration of Dr. Martin Luther King Jr. is Sunday, Jan. 17, at 7:30 p.m. at the Sarasota Opera House. On MLK Day itself, the city usually hosts a Unity Walk in Newtown. Planning a trip that weekend? See our long weekend guide.
• Jan. 21 to 25: Forks & Corks, the region's big food and wine festival, with winemaker dinners at local restaurants. The Grand Tasting is Sunday, Jan. 24, in the courtyard of the Ringling Museum of Art. VIP and early access tickets go on sale Nov. 3, and general admission Nov. 10. It sells out, so set a reminder.
• Jan. 30 to 31: the 24th annual St. Armands Circle Art Festival, the Circle's winter show.

February 2027

February is peak season. It's also when the arts calendar is at its fullest.

• Feb. 6 to March 21: the opera's winter season at the Sarasota Opera House, 61 N. Pineapple Ave. La traviata opens Feb. 6, H.M.S. Pinafore Feb. 13, Ariadne auf Naxos Feb. 27 and Jenůfa March 6.
• Feb. 12 to 14: the touring musical Water for Elephants at the Van Wezel Performing Arts Hall. A circus story in the old winter home of the circus feels right.
• Feb. 13 to 14: the 39th annual Downtown Festival of the Arts, with artists lining Main Street. It has been free in past years.
• Presidents Day weekend, Feb. 13 to 15: Valentine's Day falls on Sunday, so book dinner early.
• Feb. 19: Orioles spring training opens at Ed Smith Stadium against Atlanta. There are 15 home games, through Friday, March 19, against the Yankees. MLB's labor agreement expires Dec. 1, 2026, so keep an eye on Orioles.com for any schedule changes. Our spring training guide covers tickets, parking and bag rules.
• Feb. 19 to 21: the 29th Thunder by the Bay Music & Motors Festival at the fairgrounds.
• Feb. 20 to 21: the 6th annual Longboat Key Festival of the Arts.
• Feb. 27 to 28: the 5th annual Sarasota Festival of the Arts at J.D. Hamel Park on the bayfront.

Our art festivals calendar lists every show for the season in one place.

March 2027

• Spring training: Orioles home games continue through March 19.
• Spring break: usually early March to early April, when beach lots fill early on weekends. Our spring break guide covers what to book ahead.
• March 20 to 21: the 5th annual Downtown Fine Art and Craft Fair. The 2026 edition was on Main Street at Orange Avenue.
• March 21: the opera's winter season closes.
• Easter Sunday, March 28: sunrise services, brunches and egg hunts usually fill the weekend. See our Easter guide.

April 2027

April is still busy, but it's the last stretch of the high season. The Gulf warms up and the days are long.

• Film festival: the Sarasota Film Festival is usually held in April. The 2026 edition ran April 10 to 19. Check sarasotafilmfestival.com for 2027 dates.
• Late season: once spring break ends, beaches and restaurants get a little easier, while the weather stays warm and dry.

How to Plan Around Winter Events

• Check dates the week you go. Organizers can change hours or move an event for weather. Use the official site, not a listing that copied it.
• Go early to festivals. The outdoor art shows usually open at 10 a.m. and are calmest in the first hour.
• Park once. On St. Armands, the city garage at 57 N. Adams Drive gives you the first hour free once you register your plate, then a small hourly rate. Rates can change for special events, so read the signs.
• Use the free trolley. The Bay Runner connects downtown, St. Armands and Lido Beach, which makes festival weekends much easier. Check the current schedule.
• Book the big nights. Dinner on the night of a tree lighting, Valentine's Day or a Saturday in March needs a reservation.

Still choosing a month? Our guide to the best time to visit compares weather, water temperatures and crowds.

What to Bring to Winter Events

Winter days are warm, but outdoor evenings like the tree lighting or the boat parade can get cool by the water. A few things from The Sarasota Style that work well:

• A layer for evening events. The women's Longboat Key Mock Neck and the Lido Key Timber Crew are easy to carry and warm enough for a breezy night.
• A hat for festival days. Art shows and ballgames mean hours in the sun. The Siesta Key Cap in sand is a good pick.
• Sunscreen. The sun is strong even in January. We carry Sun Bum Mineral Sunscreen Spray.
• A souvenir from more than one island. The Keys Tee has a map of all the keys.

We're at 410 St. Armands Circle, open every day from 9 a.m. to 9 p.m., right in the middle of the Circle's art festivals and the Holiday Night of Lights. Stop in and say hello. Building your trip around one of these weekends? Start with our 3-day itinerary.