Upcoming Events around Siesta Key

paddle boarding

Vacationing on Siesta Key is wonderful any time of the year, but it’s even more fun if you book your trip around one of the special events that take place throughout the year. 

Here are some upcoming events on Siesta Key and its surrounding areas. 

2024 ICF Stand Up Paddleboard (SUP) World Championship: Nov. 19 – Nov. 24, 2024

Nathan Benderson Park is a popular place for outdoor activities in Sarasota and the surrounding region. It’s 550-acres centers around a 400-acre lake with a walking/running/biking trail and plenty of picnic areas. It’s most notable for holding the Olympic rowing trials, and athletes come from around the world to train year-round. 

But it’s also a popular spot for paddleboarding, kayaking, and other water sports.  The SUP World Championships feature the top athletes in this sport competing to be crowned the world’s best. 

If watching these top athletes inspires you to make your own attempt at killing it on a paddleboard.  there are plenty of gear and adventure rental agencies near the Sea Shell. Most will deliver the paddleboard equipment and get you set up and started. 

Thanksgiving Day Dinners in Siesta Key

Fall is an amazing time to visit the beautiful beaches of Siesta Key. The air is balmy, the water is still warm, and it’s not as crowded as the traditional “high season” of January through April.

If you are staying at a fully furnished condo like we have at the Sea Shell, making your own Thanksgiving dinner is very convenient. All the kitchens are stocked with everything necessary to prepare and serve even the most complex meal. And, of course, watch football on your big screen TV while you digest.  

But you’re on vacation, so why not just let someone else deal with the cooking and cleanup? There are a number of restaurants in Siesta Key and the surrounding area that serve traditional Thanksgiving dinners as well as menu options for those who are not turkey fans – or who don’t necessarily observe Thanksgiving. Click here for 5 that we highly recommend.

Siesta Key Light Up the Village & Holiday Parade: Nov. 30, 2024

Just hop on the free trolley for the few minute ride to Siesta Key Village. It’s a fun place to visit even when nothing special is happening, but holiday events like these really highlight the community spirit and beach vibe of this special place. The parade starts at 5 p.m. and children can have pictures taken with Santa from 2 p.m. to 4 p.m. 

Coincidentally, this is also Small Business Saturday, so get there early to patronize the many small businesses in the Village. We encourage you to check out our Dining and Shopping guide To learn more about what you can find in the Village.

Siesta Beach Seafood & Music Festival: December 1– 3, 2024

Live music all day, every day, and LOTS of awesome food. The seafood dishes are prepared using fresh, local, sustainable ingredients. There are also vegetarian offerings as well, so no one needs to feel left out. Alcohol is available for those over 21, non-alcoholic for the young, or for those who choose not to imbibe.

During lulls in the music, take some time to browse the arts and crafts and other local items available for sale at the many vendor tables.  You can get there from the Sea Shell by walking north on the beach, or take the free trolley.

Location: Siesta Key Public Beach Pavilion.

Hours: 12 p.m. to 9 p.m. Friday; 11 a.m. to 9 p.m. Saturday; 11 a.m. to 6 p.m. Sunday

Lakewood Ranch Bluesfest: December 7, 2024

Located about 40 minutes from Siesta Key, Waterside Place in Lakewood Ranch is the site of many events and activities, and the inaugural Lakewood Ranch Bluesfest is getting a lot of buzz. Seven different acts will perform from 10 a.m. until 7:40 p.m.

Waterside Place also hosts a weekly farmer’s market and plenty of community nights with music that are open to anyone. It’s a great place to walk around, get a bite to eat, and enjoy a beautiful evening.

Address: 7301 Island Cove Terrace. Lakewood Ranch, FL 34240

New Year’s Eve Pineapple Drop Block Party in Sarasota: December 31, 2024

Who needs NYC and the disco ball? Sarasota has the giant, glowing pineapple! The Pineapple Drop Block party runs from 1 p.m. on New Year’s Eve until 1:30 a.m. on Jan. 1, 2025. There are carnival rides, food booths, art and craft vendors, and more – including fireworks after the pineapple drop. Pretty much everything you’d expect from a great community event.

Admission is free; unlimited ride wristbands (for riders 36 inches and taller) are $30 while supplies last. Getting them online before the event is the best way to ensure availability. Visit the webpage for more information.

Address: Downtown Sarasota, 1 N. Lemon Street