Whether you’re visiting Siesta Key for a short vacation or planning a longer-term “snowbirding” stay, knowing the local events can help enrich your stay! Or, at the very least, give you something to do besides soak in the sun and sand on the beach.
Nearby Sarasota offers a wide array of reoccurring events, from bustling farmer’s markets to novel concerts, plays, and art exhibits. This rotating cast of attractions ensures you can keep the family entertained regardless of your interests. Get to know Siesta Key through immersion in the local community and stay in one of our conveniently located beachfront rental properties for maximal Florida fun.
Here’s a look at all the best reoccurring events in Siesta Key and the surrounding area.
Year Round Events in Siesta Key
Siesta Key Farmers Market
- Sundays, 8 AM to Noon
- 5211 Ocean Blvd, Siesta Key, FL
- Best for shopping for local artisanal goods and groceries.
Stroll through the village’s quaint streets accompanied by live music and most of the Siesta Key populace. You can find quality crafts, savory & sweet baked goods for take-home treats, and loads of quirky giftable items for your friends and family back home.
Siesta Key Drum Circle
- Every Sunday, one hour before sunset, Siesta Key Beach.
- Family-friendly festival atmosphere
This weekly event also happens to be the most popular event for onlookers, not just the musically inclined either. Watch as the boho residents of Siesta Key make magic through dance and music in one of the largest drum circles in the nation. It’s not uncommon to spot some sword-swallowing, belly-dancing, and fire-dancing as the sun sinks beyond the horizon.
Seasonal Events in Siesta Key
Now that we’ve covered the regularly scheduled events in the Siesta Key Village, here’s a look at the calendar across the seasons.
Winter Events
The warm Florida winters offer the perfect time to celebrate Christmas in Siesta Key as well as plenty of fun events in other months for you and the family! Here are a few of our favorites.
Sarasota Winter Carnival
- Mid-January at the University Town Center (UTC)
- Best classic carnival for the whole family.
This fluorescent family fun festival has all your classic yet thrilling carnival rides. Whether you’re a fan of the deep-fried food or looking for some adrenaline-inducing twirls and spins, the five-day annual event is well worth a visit if you’re in town. The powder-sugar-dusted funnel cake is a tried and true foodie favorite. Just be sure to hit the rides before you fill up.
New Year’s on Siesta Key
- December 31st
- Best for those hoping to celebrate the New Year with fireworks and a cocktail in hand.
There is no shortage of events where you can ring in the New Year on and around Siesta Key. Locals will usually head to Gilligan’s Island Bar and Grill or The Beach Club for a late-night party.
Read our full guide on the Winter Fine Arts Festival for yet another wintertime event option.
Spring Events
Celebrate Spring in style with the whole family in Sarasota.
Berry Fest
- Weekends in March at Fruitville Grove
- Best for those looking for a family-friendly event.
Head to Fruitville Grove with the whole family to snack on light and fluffy strawberry shortcakes, fruity pastries, and other fruit-forward lemonades and sweet treats. All while being entertained by local vendors, scenic kiddie train rides, and baby animals.
Sarasota Film Festival
- Late March to Early April
- 332 Cocoanut Ave. Sarasota, FL
- Best for film buffs and their families.
The Sarasota Film Festival is a 10-day celebration of film throughout the genres. Complete with red-carpet premieres, short films, documentaries, and more.
Check out the Downtown Sarasota Art and Craft Festival and Sarasota County Fair as well.
Summer Events
Turn up the heat this summer with a few Sarasota events centered around music and, of course, our very own Fourth of July celebration.
Sarasota Music Festival
- Late May to Early June
- 709 N. Tamiami Trail, Sarasota, FL
- Best for classical music enthusiasts.
Thanks to the Sarasota Orchestra, the city has been hosting this excellent classical music festival every June for 60 years now. Stop in at least once during the festival’s three-week duration if you have any interest in witnessing musical genius from students across the country.
Siesta Key Fireworks Show
- 4th of July
- Best for those planning a visit over the national holiday.
If you happen to be visiting Siesta Key during Independence Day, fret not, Florida knows how to celebrate the birth of America. Head to virtually any slice of Siesta Key Coastline for an excellent view of the colorful fireworks display just after dark. This is far from the only fireworks show in the area. If you’re in a good vantage point, you’ll witness both the Sarasota Fireworks and Venice Fireworks simultaneously.
Fall Events
September, October, and November bring a wide array of festivals to the streets of Sarasota. In fact, this is the best time of year to visit if you want to attend an event in Siesta Key.
Fruitville Grove Pumpkin Festival
- Weekends in October
- 7410 Fruitville Rd, Sarasota, FL
- Best for family fun that celebrates the autumn season.
Channel your spooky Halloween spirit at this weekly event in October. Pumpkin picking, hay rides, pony rides near the petting zoo, live music, and fall-themed eats make this a must-see family affair. Adults will enjoy the freshly baked pumpkin pies and craft fair with fun fall souvenirs.
Lakewood Ranch Blues Festival
- Early December
- Waterside Park 7301 Island Cove Terrace Lakewood Ranch, FL
- Best for Blues Music lovers.
Hoping for a classy induction into the performing arts? This celebration of blues is the perfect soulful atmosphere on the spectacular Lakewood Ranch as it brings excellent musicians from around the globe to the region. Don’t skip the local food and beverage vendors— namely the BBQ and craft beers.
Siesta Key Crystal Classic
- Mid-November
- Siesta Key Beach
- Best for beachy strolls and families.
If you’ve ever tried to mold the perfect sand sculpture, you understand the delicate craftsmanship that goes into even the simplest creation. But these are far from simple creations. Come stroll the beach and marvel at the 10-foot-high masterpieces of some of the country’s best sand sculptors as they painstakingly coax the sugar-white sand into flawless structures. An excellent event for kids and
Siesta Beach Seafood & Music Festival
- Early December
- Siesta Key Pavilion
- Best for food lovers looking to sample the creations of the region’s top chefs alongside musical performances.
Siesta Beach Seafood & Music Festival is the place to be for live music and local seafood. It doesn’t get much better than this. With local and regional music ranging from rock to reggae accompanied by bites of buttery lobster and locally famous fish tacos, this is an adult event perfect for a group of friends or a romantic evening.
Sarasota Chalk Festival
- Early November
- Visit their website for this year’s locations.
- Best for quirky art lovers and families looking to explore a new area of town.
When you’ve finished marveling at the sand creations, come check out these sidewalk masterpieces. The annual Sarasota Chalk Festival brings talented chalk artists to the streets of Sarasota (literally), creating 3D masterpieces that are so far from your childhood chalk renditions that you’ll be amazed.
Sleep Sweetly in Sarasota County on Siesta Key!
With so many fun things to look forward to on your next trip to Siesta Key (or nearby Lido Key & Longboat Key), don’t wait to start planning your vacation! Browse our group vacation rentals and quaint village-center apartments early to secure the best stay on Siesta Key. Between beach club dinners and special festival events, you can relax comfortably and make Siesta Key a part of your annual traditions.
For a full calendar of upcoming events, check out Sarasota’s official website.