Most Popular Annual Events and Festivals Coming Soon in Siesta Key, Sarasota, and Lido Key

Siesta Key is the perfect spot for a family getaway. Everyone from the foodie to the history buff will be in paradise thanks to all the great attractions nearby. In addition to all of the year-long activities, there are also tons of fun annual events happening in the area.

Best of all, each festival is just minutes from our luxury resort accommodations. There are not many Siesta Key Beach hotels to choose from, but The Tropical Breeze Resort is the only one within walking distance to both the beach and Siesta Key Village. Here are 10 of the most popular events in and around Siesta Key.



New Year’s Eve at Marina Jack

Marina Jack in downtown Sarasota is in the perfect spot for watching the fireworks on New Year’s Eve. You can enjoy food, live music, and the Pineapple Drop along with the fireworks. Marina Jack is located at 2 Marina Plaza in Sarasota, and the event happens all night on December 31.



Sarasota Winter Fine Arts Festival

Every January, Sarasota welcomes more than 100 of America’s top artisans to display their crafts. At this fun annual event, you’ll see photographs, glasswork, jewelry, sculptures, and so much more. This free event takes place over a weekend in January and is located on Gulf Stream between McAnsh Square and Coconut Avenue.

Pioneer Picnic

Sarasota’s annual Pioneer Picnic has been welcoming guests since 1974 and helps educate the public and celebrates everything amazing about the city. Every February, guests come from far and wide to enjoy incredible food and unique history. Register early for a discounted fee. This event takes place in early February at Robarts Arena.



Siesta Key Village Pub Crawl

Every year for St. Patrick’s Day, Siesta Key holds a pub crawl to get you in the spirit. You’ll get a taste of all the best bars in the area, and you can do some souvenir shopping while you’re at it. This event is constantly changing, so do some more research closer to St. Patrick’s Day for more information.



Florida Winefest

The annual Florida Winefest and Auction takes place each April. You can sample wines, enjoy brunch, and meet local winemakers during the four-day festival. Location and prices vary each year.

World Oceans Day Festival

June 8 is World Oceans Day, so come out to Emerson Point Preserve and enjoy the festivities. You can learn about wildlife, take part in some ocean-themed activities, and even get the opportunity to test a kayak!

Free Fall Festival

Every September, Sarasota holds its Free Fall Festival, a fun way for the whole family to get into the fall spirit. This event features fun activities like a dunk tank, face painting, bounce houses, and more. All proceeds from beer sales benefit Heroes Welcome Home. The Free Fall Festival takes place in mid-September at the Florida Farm Bureau Pavilion in Sarasota.



Fruitville Grove Pumpkin Fest

Each October, local vendors come together to hold the Fruitville Grove Pumpkin Fest. This free event offers music, shows, kids’ activities, local crafts, and so much more. Be sure to grab a pumpkin and support the local farmers! Pumpkin Gest lasts all throughout October from 9 a.m. until 6 p.m. on the weekdays.



St. Armand’s Fright Night

Every Halloween, St. Armand’s welcomes guests to enjoy the holiday with their annual Fright Night. Enjoy stopping by the local restaurants and shops to show off your costume and get a fun treat. This event is typically held from 6 – 9 p.m. on Halloween.

Annual Gingerbread House Festival

During the first week of December, be sure to come out to the Annual Gingerbread House Festival at the Mall at UTC in Sarasota. Local organizations and groups come together to display their creations, and you can even pick up a centerpiece for your own gingerbread house. Admission is only $1!

Choose Your Resort Room

This is just a handful of the fun events happening throughout the year in and around Siesta Key. By staying at our Siesta Key hotel near the beach, you will have access to all this and more, adding a special touch to your dream vacation. For more information on annual events in the area as well as our Siesta Beach resort, contact us today!

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