Siesta Key Events To Get You In The Holiday Spirit

Deck the palm trees and break out the sunscreen – it's holiday time at Tropical Beach! Whether you’re a Florida native or just visiting for the winter, Siesta Key is the perfect place to celebrate the holiday season. From holiday markets, boat parades, and Christmas tree lightings, we’ve got plenty of ways for you and your family to ring in this holiday season. Check out our local list of the best things to do in December during your stay at Tropical Beach Resorts.

Outdoor Holiday Market at University Town Center

Get ready for the ultimate shopping extravaganza! Featuring more than 150 different vendors, this two-day festival is a must-do on your trip. Find last-minute Christmas gifts, specialty food trucks, and more at this annual market. This two-day market will be held on December 1st and 2nd, with times varying on each day (4pm - 9pm on Friday and 11am - 5pm on Saturday).

Admission and parking are free! For more information, visit the University Town Center website here

Photo courtesy of UTC

Gingerbread Festival

What better way to celebrate the holiday season than gingerbread houses? Join the Girl Scouts of Gulfcoast Florida for their 15th annual Gingerbread Festival at University Town Center from December 1st to 10th. Feast your eyes on 150 gingerbread houses crafted by local schools and organizations. Best part? It's free! The festivities run from 6:30 pm to 9:30 pm daily. 

More information on this gingerbread goodness here

Venice Christmas Boat Parade

Set sail for the Intercoastal Waterway on December 2nd at 6 PM and catch the Venice Christmas Boat Parade. Watch in awe as boats decked out in Christmas glory cruise by. Admission is free and this event is open to the public. 

For boat paths, viewing areas, and more information, visit the Venice city website here

Sarasota Ballet School Presents The Nutcracker

The Sarasota Ballet School partnered with The Venice Symphony will put on two performances of The Nutcracker on December 8th (7pm showtime) and December 9th (3pm showtime). Tickets range from $35 - $75  so be sure to snag yours at the venue’s box office.

For more information, visit the venue’s website here.

Ugly Sweater Crawl

Grown-ups: it’s time for a night out and to bust out the ugly sweaters! The 6th annual Ugly Sweater Bar Crawl is here and waiting for you. The crawl is on December 9th, from 4pm - 9pm. For $17, you'll score tickets to 5 participating bars.

Grab your ugliest sweater and visit the event site here

Photo courtesy of Event Vesta

Winter Nights Under The Lights

From December 13th - 17th, enjoy Palma Sola Botanical Park’s Winter Nights Under The Lights! The event features food trucks, live music, a golf cart parade, hay rides, crafts, and more! The best part of it all is the acres of twinkling lights! While admission is free, donations are highly encouraged. 

The event is nightly from 6pm - 9pm, and for more information visit the event page here

Chanukah at Fisherman’s Village

Enjoy the annual celebration of Chanukah at Fisherman’s Village. The event will feature live music along with beloved Chanukah treats for attendees to enjoy. Watch the lighting of the Menorah and enjoy the last day of Chanukah on December 14th at 6pm. 

For more information, visit the event site here

Photo courtesy of

Siesta Key Christmas Beach Service

Sand between your toes, sea breeze in your hair, and Christmas spirit in the air – that's the Siesta Key Christmas Beach Service for you! This Christmas service is hosted by the Church of the Palms, with services on December 23rd at 5pm or Christmas Eve services at 5pm, 7pm, 9pm & 11pm.

For location details and more, visit the Church’s website here.

New Year’s Eve Pineapple Drop in Sarasota

Ring in the New Year with a splash at the annual Pineapple Drop! It's a downtown block party that’s fun for all ages with live music, carnival games, food, and drinks. General admission is free, but beware that this attraction is one of the most popular events in town and is expected to bring in 20,000 people to downtown Sarasota (plan accordingly)! 

This is an all day event, running from 1pm - 1am. For more information, visit the event website here

Photo courtesy of Herald-Tribune

There you have it – a sleigh-load of festive fun awaits you at Tropical Beach and beyond. However you choose to celebrate, we're sending you sandy, sunny wishes for a holiday season that's as bright as our Florida sun. Can't wait to see you in the New Year for more beachside memories at Tropical Beach!