Winter is here, and while the rest of the country is huddled indoors, we in Sarasota and Bradenton get to enjoy the cooler weather without all the snow and ice. It’s that perfect time of year when you can finally step outside without immediately melting.
In this post, we bring you a list of five incredible winter activities that are too good to miss. Let’s dig in immediately and find ways to revel in true holiday spirit:
1. Poinsettia Parade & Festival
Date: December 7, 2024
Location: City Center Campus, 4970 City Hall Blvd., North Port, FL
If there’s one thing that screams holiday spirit, it’s a parade, and North Port knows how to throw a good one. This annual event kicks off with a festival from 3 PM to 7 PM, complete with live music, craft workshops, and a magical kids’ zone. Oh, and Santa? He’ll be there too, ready for selfies and wish lists.
The real showstopper, though, is the parade at 5 PM. Imagine twinkling floats adorned with poinsettias, marching bands playing holiday tunes, and the kind of community spirit that warms your heart.
The parade winds its way down Sumter Blvd., ending at the festival grounds where the party continues with food, vendors, and live performances.
2. Wonderland: Illuminate
Dates: November 22 – January 5, 2025
Location: Big Top at UTC, 195 University Town Center Drive, Sarasota, FL
This year’s lineup is stacked with talent you don’t want to miss. You’ve got the hilarious Johnny Rockett keeping you laughing until your sides hurt, Ty McFarlan electrifying the stage with his unbelievable skills, and Sarasota’s own daredevil legend Nik Wallenda bringing that edge-of-your-seat thrill.
The most amazing part of this event is how it takes you on a journey through holiday traditions from around the world, so it’s like a mini vacation without ever leaving town.
When the lights dim and the music starts, you’ll forget everything else. You should bring the whole family here, and let this dazzling show remind you why winter in Sarasota is pure magic.
3. Jazz at the Cabaret
Date: December 16, 2024
Location: FST’s John C. Court Cabaret, Downtown Sarasota
Okay, this one might not be exactly outdoors, but honestly, the warm, intimate vibes of the John C. Court Cabaret will have you feeling like you’re nestled up in the coziest winter wonderland.
On December 16th, Jazz at the Cabaret presents the Greg Caputo Septet. This incredible group of musicians will have you swinging in your seat with their infectious energy.
Just imagine what it would feel like to be sipping on a warm beverage (or alcohol, whatever works best for you), surrounded by the rich sounds of jazz classics. Honestly, there is no better way to unwind after a day of holiday shopping or exploring the town.
Doors open at 6:30 p.m. for food and drinks, so arrive early, grab a cocktail, and soak in the downtown Sarasota charm before the magic begins at 7:30.
4. The Sarasota Medieval Fair
Date: November 2 – December 1, 2024 (weekends and Veterans Monday, Nov. 11)
Location: Woods of Mallaranny, 29847
If you haven’t experienced the Sarasota Medieval Fair yet, you’re seriously missing out. This annual event, held at the stunning Woods of Mallaranny (with 47 acres of gorgeous nature around you), transports you to a different time; one filled with knights, jousts, and grand feasts.
5. Holiday Boat Parade
Date: December 21, 2024
Location: Bradenton Beach Marina, located at 402 Church Ave, Bradenton Beach.
The Bradenton Beach Holiday Boat Parade is set for December 2, 2023, from 5:00 PM to 10:00 pm. The parade will begin at Longboat Key Pass and finish at the Bridge Street Pier.
During this parade, you’ll see boats decorated with sparkling lights cruising along the waterways, while you enjoy a hot drink from a waterfront restaurant or a comfy park bench along the shore.
You also get a front-row seat to the ultimate winter spectacle, with views that are absolutely perfect for a cozy evening out. Sarasota and Bradenton each have their own boat parades, where everything from the yachts to the small sailboats gets in on the holiday spirit.
If you’re looking for a laid-back but spectacular event, this is where you want to be. You’ll be in awe of the creativity and care that goes into each boat’s design – and hey, who doesn’t love a festive evening by the water?
Wrapping Up
Now that you’ve got a glimpse of how amazing winter can be here, why not make Sarasota or Bradenton your home for every season?
Sarasota and Bradenton are more than just places to visit once in a blue moon. They’re places to live, thrive, and make cherished memories.
If you’re ready to experience this enchanting winter for yourself, let Jennette Properties find a home that puts you right in the heart of it all. Contact us today so we can work together to make this winter the beginning of your Sarasota story!
