White sand beaches and alluring turquoise waters are what likely first come to mind when you think about a Siesta Key, FL, vacation, but you should add a Siesta Key festival to your to-do list on your next stay on this barrier island.

Celebrating arts and crafts, food, music, and more, a Siesta Key festival offers a unique opportunity to have fun while you immerse yourself in the area’s cultures, interests, and local talents.

There’s a Siesta Key art festival, a Siesta Key musical festival, a seafood festival, and even a sandcastle festival—a sand sculpting event that draws competitors from around the world!

If you’re lucky enough to be vacationing in Siesta Key during the time that any of these festivals are taking place, you are in for a treat!

Festivals Near Siesta Key

Let’s take a detailed look at the festivals that take place in or near Siesta Key throughout the year. You’ll see that there’s something for everyone at each one of these exciting events, just like there is the perfect Siesta Key vacation rental for everyone.

Chalk Festival

If you ever loved chalk drawing all over your sidewalks and driveways when you were a child, or if your children today enjoy this pastime, then the annual Chalk Festival is for you.

This event began in 2007 in Sarasota and moved to nearby Venice, FL, in 2014, this Siesta Key Chalk Festival has grown so much throughout the years that artists from multiple countries now attend and participate in the event. It has at times even been held in a few locations so all artists could produce their pavement chalk masterpieces. In 2010, the event became an international pavement art festival.

During this unique festival, artists create 3-D works of art for spectators. Donations of $10 for adults/$5 for students are encouraged and parking is free.

Immersion Rooms

Before the event, “immersion rooms” (which are wooden platforms constructed to display pavement art on upright canvasses) add another element to the incredible exhibition.

These “rooms” offer great photo opportunities and a different way in which to enjoy the uniqueness of sidewalk art.

Avenue of Art Exhibition

During the COVID-19 pandemic, sidewalk Picassos created their stunning works of art wherein visitors could stroll along a predetermined route to take in their completed projects.

Starting on the southeast corner of Oak Street and South Orange Avenue, the stroll continues north to Laurel Street, where you cross the street and take in more art on Laurel and Orange Avenue. Then, go to the other side of The Fountain and continue north up South Pineapple Avenue to Dolphin Street, where you will cross over to the west side of Pineapple and continue south. The Avenue of Art stroll ends at the corner of South Pineapple and Oak St.

Parking is free; donations are highly encouraged.

Past Chalk Festivals have included music, drinks, food vendors, and displays of other types of art.

The Siesta Key Crystal Classic

Detailed sand sculptures are always a source of amazement, and your jaw will be dropping when you take in the Siesta Key Crystal Classic, an international sand sculpting festival drawing professionals from in and outside of Florida.

Held each November and spanning four days, the Siesta Key Crystal Classic allows artists to create solo and team sculptures and one large community sculpture. There are a total of 24 sculpting hours spread over the event’s four days.

Visitors use wooden tokens to vote for the People’s Choice Award. Other attractions include a contest speed called QuickSand and an Amateur Competition. There are also sand sculpting lessons and live music in an entertainment tent.

History

The Classic was founded in 2010 and is modeled after other competitions held in Ft. Myers, FL, as well as in other states such as Texas and Virginia.

Noting the joy of working with the white sand popular on Siesta Key beaches and the awe-inspiring “marble-like” look of the finished products (some over ten feet tall!), sculptors have continued to be drawn to this event over the years. Today, 40,000 attend the Classic and over $9 million is raised for the local community.

Sarasota Medieval Fair

For the past 18 years, the Sarasota Medieval Fair has brought ancient times back to life every weekend during November.

You’ll encounter knights, jesters, belly dancers, and other medieval characters when you attend this popular event. In 2022, the event found a new home in the 47 acres of The Woods of Mallaranny, containing grass meadows, winding creeks, and towering oaks.

From full-contact jousting between armored knights to Human Chess Match tournaments, there is plenty of fun to watch when you attend this festival. In 2022, a Viking battle was added to the list!

There are rides, games, costume contests, and food as you might have found during the Knight Days, such as ales and massive turkey legs.

Single- and two-day passes as well as seasonal passes are available. A VIP add-on includes access to the VIP tent and photo booth for all eight festival days, as well as reserved parking, shaded seating with seat cushions for shows, and more.

The festival is held Saturday and Sunday 10 a.m. – 5:30 p.m., rain or shine.

Siesta Key Rocktoberfest

Food and tunes are the highlights of Siesta Key Rocktoberfest, a Siesta Key music festival held in mid-October in JD Hamel Park in downtown Sarasota.

The second annual event was held October 14-16, 2022, with the third annual planned for October 13-15, 2023.

Of course, live music performances are the main events, but there is plenty of food to choose from. You’ll find a wide variety of German dishes, such as Schweinshaxe (roasted ham hock), Wurstl (Sausages), Kaesespaetzle (cheese noodles), sauerkraut, and more. You’ll also find German and other types of beer.

In addition to German music and dancing, you’ll find soul, R&B, rock, and other music performances.

The three-day event runs Friday – Sunday; 4 p.m. – 10 p.m. Friday, 11 a.m. – 10 p.m. Saturday, and 11 a.m. – 6 p.m. Sunday.

Siesta Beach Seafood & Music Festival

In early December, head to the Siesta Key Pavilion in Siesta Beach for the 5th Annual Siesta Beach Seafood & Music Festival.

This festival has it all: besides freshly cooked seafood from local sources, you can enjoy live music and a shopping marketplace with arts and crafts, food, and other items.

Like Rocktoberfest, this is a three-day, Friday – Sunday event: noon – 9 p.m. Friday, 11 a.m. – 9 p.m. Saturday, and 11 a.m. – 6 p.m. Sunday.

Where to Stay in Siesta Key

For accommodations, many Siesta Key vacation rentals are conveniently located near these festivals.

You can choose from two- to four-bedroom beachfront condos and three- to eight-bedroom vacation homes that comfortably sleep up to as many as 24 guests! Depending on your choice, you might enjoy such luxurious features as rooftop decks, heated pools, and tiki huts.

When you choose one of these rentals, you’ll enjoy fully-stocked kitchens, spacious living areas, flat-screen TVs, king- and queen-sized beds, and a washer/dryer. Luxury services include linen service, grocery delivery, and discounts from local vendors.