botanical garden decorated with christmas lights
"Lights in Bloom" at Marie Selby Botanical Gardens Downtown Campus

Must See Holiday Traditions in Sarasota County

From sand art to comfort food to light shows and a... pineapple drop? Consider trying one of these local traditions while you visit in the winter.

September 2, 2020

artist drawing on ground with chalk

Chalk Festival (Postponed to 2021)

“Hailed as the most important pavement art event in the world,” it’s no surprise CNN  named the Sarasota Chalk Festival one of the best in its class. From start to finish, you can witness the largest gathering of prominent pavement artists perform using the road surface as a canvas to develop oversized masterpieces in chalk. Since 2010, the festival has featured the largest display of 3D pavement illusions in one location, “more than any other place or any other time in the history of the art form.” From the right perspective, these chalk landscapes jump off the asphalt as a 3D picture comes into focus. Guests are encouraged to become part of the art, walking right up against – even on top of – these intricate diagrams as if they are stepping into the imaginary scene itself!

picture of paul rudolph umbrella house in sarasota county, florida
(Photo: Sarasota Architectural Foundation)

Sarasota MOD Weekend

Did you know sleepy Sarasota was part of a mid-century modern architecture renaissance following World War II? The Sarasota Architectural Foundation hosts a weekend of tours, art exhibitions, film screenings and lectures about the area’s design influence and legacy. In true artistic fashion, the 7th annual Sarasota MOD Weekend has been adjusted to handle the challenges of the COVID-19 pandemic with a new socially distant and virtual schedule of events designed in collaboration with 2020 honoree—architect Carl Abbott.

Der Dutchman Pies photo
Der Dutchman Sarasota

Authentic Amish Pies in Pinecraft

For non-Amish visitors, Pinecraft and its residents are best known for the food, and perhaps the most famous of these items are the baked desserts. More specifically, the pies that people line up around the block to wait for as the grand finale to their holiday meals. Yoder's Amish Village has recently estimated making up to 8,000 pies on the eve of major holidays—more than 25 different varieties still using Mrs. Yoder's original recipes. Just to the east is the Der Dutchman, also famous for its hearty, home-cooked meals and, you guessed it, pies! Grab one for your family on or around the holidays and we promise you’ll dream about these pies long after you leave Sarasota.

Sailor Circus

For a uniquely Sarasotan experience, be sure to catch a Sailor Circus high flying holiday performance to close out the season. For more than 70 years, youth performers ages 8 to 18 have honed their craft at The Greatest “Little” Show on Earth making it the longest running youth circus in America. Their holiday-themed performances in the winter often feature aerialist acrobatics, lightning-fast juggling and other gravity-defying stunts! Not to mention fans can catch a glimpse of the recently upgraded circus arena the group calls home.

The Westcoast Black Theatre Troupe

A Motown Christmas

Westcoast Black Theatre Troupe (WBTT)—the only professional black theatre company on Florida’s West Coast—debuted this popular holiday show in 2015. Created and adapted by founder/co-owner Nate Jacobs, it’s a joyous and fun holiday revue with a blend of the traditional and the soulful sounds of Motown celebrities like Marvin Gaye, Stevie Wonder, The Supremes and more! WBTT’s dazzling style will make this one holiday show you won’t forget.

The Ca' d'Zan mansion at The Ringling

Deck the Halls at the Ca’ d’Zan (Postponed to 2021)

NOTE: guests can still experience a self-guided tour of the first floor decorations in the Ca' d'Zan in 2020.

If you want to see how the wealthiest couple in America used to celebrate the holidays, The Ringling will decorate the former home of circus magnate John Ringling (a.k.a. The “Ca’d’Zan”) to the nines as if Ringling himself was going to walk out and greet you as a guest! Keep an eye out for special tour times and other fun events hosted each year by the state art museum of Florida on its massive bayfront property.

botanical garden decorated with christmas lights

Lights in Bloom at Selby Gardens

Marie Selby Botanical Gardens puts on one of the most spectacular light displays of the season at Lights in Bloom —named the #9 best botanical garden holiday light display in the country. The breathtaking gardens at Selby’s downtown campus are transformed into a tropical holiday paradise with over two-million lights that set the bayfront property aglow.

pineapple made of holiday lights

New Year's Eve Pineapple Drop (Postponed to 2021)

Since 2000, downtown Sarasota welcomes everyone to ring in the New Year at a free block party along Main Street. It is described by locals as the biggest New Year’s Eve celebration in Southwest Florida, known for dropping a bright, decorative pineapple at midnight—much like how New York City drops an apple. Festivities include amusement rides, multiple live music stages, beer and food vendors within walking distance of Main Street. The lighted pineapple hangs from a crane above the festivities all night until it is lowered during the ten-second countdown to midnight. Then, a spectacular fireworks display explodes along Sarasota Bay for thousands to marvel and applaud.

Back to the Holiday Guide

The Ultimate Holiday Guide to Sarasota County

The most wonderful time of the year lives up to the motto near the glistening gulf coast beaches of Sarasota County. The daily sunshine will make you feel warm on the outside, but there are plenty of local traditions for winter visitors that can make you feel cozy on the inside too.