Sarasota Holiday Guide: Celebrate the Season in Style

As Sarasota sparkles with holiday cheer, there’s no better way to experience its vibrant lifestyle than by diving into its festive events. From dazzling light displays to luxurious New Year’s Eve parties, Sarasota offers the perfect mix of community warmth and sophisticated celebrations. Here’s your guide to the season’s top events.

November Festivities

Sarasota Fall Carnival

📅 Nov. 15-17
📍 140 University Town Center Drive, Sarasota
Start your holiday season with a classic carnival experience. Enjoy thrilling rides, community performances, and fair favorites like fried Oreos and funnel cakes.
Hours: Friday at 5 p.m.; Saturday & Sunday at noon

Black Friday Block Party

📅 Nov. 29, 2-9 p.m.
📍 1445 Second St., Sarasota
Celebrate the biggest shopping day of the year with live music, a beer truck, a wine tent, and a lively cornhole tournament hosted by 99 Bottles.

Siesta Key Holiday Parade

📅 Nov. 30, 5:30 p.m.
📍 Siesta Key Village
This festive parade kicks off at Avenida del Mare and winds through Beach Road and Ocean Boulevard. Perfect for families seeking a cozy community vibe.

Venice Holiday Parade

📅 Nov. 30, 6:30 p.m.
📍 Venice Island
A family-friendly tradition with food and drinks sold by local nonprofits. It’s a great way to immerse yourself in the charm of nearby Venice.

December Delights

Discover Sarasota Christmas Carol Trolley

📅 Dec. 1-23
📍 1826 Fourth St., Sarasota
Enjoy a 75-minute trolley ride featuring downtown lights, caroling, and professional holiday-themed performances.

Lights in Bloom

📅 Dec. 6 - Jan. 1, 6:30-9 p.m.
📍 Marie Selby Botanical Gardens
Marvel at over 2 million lights illuminating the stunning botanical gardens. Food and drinks are available, making it an enchanting evening outing.

Downtown Sarasota Holiday Parade

📅 Dec. 7, 7 p.m.
📍 Main Street, Downtown Sarasota
With over 4,000 participants, lighted floats, school bands, and a visit from Santa, this is one of Sarasota’s most beloved traditions.

Sandy Claws Beach Run

📅 Dec. 14, 8 a.m.
📍 948 Beach Road, Siesta Key
Run or walk in this holiday-themed 5K and one-mile fun run. Festive costumes are encouraged, and the event features music, food, and raffle prizes.

Sarasota Bay Holiday Boat Parade of Lights

📅 Dec. 14, 6 p.m.
📍 5 Bayfront Drive, Sarasota
Watch boats adorned with twinkling lights sail through Sarasota Bay. Arrive early at Bayfront Park for the best views.

Manatee River Boat Parade

📅 Dec. 17, 7 p.m.
📍 Multiple Manatee County locations
Cheer for boats competing for cash prizes in this festive display along the Manatee River.

Celebrate New Year’s in Style

Westin New Year’s Eve Winter Soiree

📅 Dec. 31, 9 p.m.
📍 100 Marina View Drive, Sarasota
Ring in the new year with rooftop views of Sarasota Bay, a DJ, dancing, party favors, and a midnight champagne toast.

New Year’s Eve at Waterside Place

📅 Dec. 31, 6 p.m.
📍 Waterside Place Town Center, Sarasota
Celebrate with a unique drone light show instead of fireworks—an innovative twist perfect for the Sarasota luxury lifestyle.

Downtown Sarasota Pineapple Drop

📅 Dec. 31, 1 p.m. - midnight
📍 Lemon Avenue and Main Street
This iconic event features live music, carnival rides, games, food, and drinks. Watch the pineapple drop at midnight, then enjoy special offers at local bars and restaurants.

Whether you're here to explore Sarasota’s lifestyle or already call it home, these events offer a wonderful way to embrace the holiday season. Sarasota Neighborhood Experts are here to help you discover more about the vibrant community and guide you to your dream home.

Happy holidays!