5 Fun Fall Events this Season

Looking to make the most of the holiday season this year? You shouldn’t have to choose between vacation planning and holiday spirit. Here are some great Siesta Key fall events on the gulf which are easily accessible from any of our Siesta Key condos.

Pumpkin Fest

Running through four weekends in October, Fruitville Grove Pumpkin Fest is a celebration of all things autumn. The festival takes place at a farmer’s market just east of Sarasota, with free admission and parking. It’s a great family (and dog) friendly event.

Photo from Pixabay

Activities that are sure to dazzle include circus acts, live music, amusement park rides, playing with farm animals, and all sorts of costume and pumpkin decorating. The baby goats are a fan favorite, and you can even do a yoga class with them!

A fleet of local artisans, food trucks, and other vendors are all on the premises so you can stock up on gifts and have a full meal on site.

Sarasota Medieval Fair

If you’re looking for some adventure leading into the Thanksgiving season, look no further than the Sarasota Medieval Fair! For four weekends through November 9 to December 1, The Sarasota Fairgrounds turn into a self-sustaining medieval village.

The list of spectacles is massive. A story-telling human chess match, full-contact jousting, acrobats and death-defying stunts are just some of the sights you’ll witness. Witness song and dance from Saxon warriors, Viking sailors, Shakespearean poets, and Celtic folk artists.

Experience a genuine medieval marketplace with artisans, merchants and food outlets. Adults can indulge in the pub crawl too! Sample from a dozen different ales, wines, and meads and hang out with some of the festival’s most notorious characters.

Seafoood and Music Festival

Craving an epic meal even after Thanksgiving dinner? Be sure to check out the 4th Annual Siesta Beach Seafood and Music Festival from December 6-8. It’s quickly becoming a rockin’ neighborhood tradition and is one of the biggest fall events near Sarasota!

Prioritizing sustainability, all the seafood is locally sourced and freshly cooked by some of Sarasota’s finest chefs. In past years, they’ve served up a raw bar, jambalaya, paella, bisque, and tons of other fish and crustaceans. You’ll also find land and vegetarian options, as well as mocktails and fresh juices.

The festivities take place right on the Siesta Key gulf coast with food, drink, and music all weekend long. VIP tickets provide access to a full open bar, luxury outdoor dining, and exclusive concert seating. Whether you’re into jazz or rock, contemporary or Caribbean, the music is as diverse as the food!

Holiday of the Arts

On December 7-8, 2019, the white sand beaches of the Florida gulf coast will host the magnificent Lido Beach Holiday of the Arts, just a stone’s throw away from Siesta Key.


Here you’ll find something beautiful to wear, hang up at home, or use from day to day, from paintings and photography to pottery to glass, from jewelry and apparel to metal and wood carvings.

Holiday of the Arts is quickly becoming one of Florida’s premier exhibits of handmade, artisan-crafted works. It’s the perfect pit stop if you’re looking to share an inspired gift this holiday season. For every piece available, you can meet the creator and hear the stories of their works to bring back home. The festival organizers take pride in the works they’ve assembled, which are available in all shapes, sizes, and prices.

Plan Your Stay

Make any of these events in Siesta Key are part of a trip to paradise. After a long day (or night), retire to the soft beaches, vibrant restaurants, and your home away from home at the Siesta Key beachside villas.

The Pineapple Drop

Usher in the New Year in style with the Sarasota NYE Block Party and Pineapple Drop! People from all over the country swoop in to Sarasota for this extravagant event.

Starting from 1 p.m. and going to 1 a.m., the whole downtown area turns into one big fair. Amusement rides and games start early. The block party kicks off at 5 p.m., with live music all evening long downtown at Main and Lemon streets. Restaurants and bars move to the streets, and chefs and bartenders from all over the area gather to show off their wares.

Whether you’re in the middle of the action or hanging back enjoying the company of your friends and family, you won’t miss the main event: the giant pineapple slowly descending, erupting into a fantastic fireworks show!

Our Location

Crystal Sands Condominiums
6300 Midnight Pass Road
Siesta Key, FL 34242

Toll-Free: 888-419-1446
Local: 941-349-7007

Fax: 941-346-1963

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