Holiday and Winter Events on Anna Maria Island

Will you be staying on Anna Maria Island during the holiday season? If so, you’ll be pleased to know that there are all sorts of holiday and winter events on the island that you’ll be able to partake in and enjoy. We’ve compiled five activities that are packed full of festive fun and excitement. You won’t want to miss them!

Annual Christmas Tree Lighting

The lighting of the Anna Maria Christmas tree is an annual tradition that is fun for the whole family. It occurs on the beautiful Bradenton Beach and draws in a large crowd of locals. This celebration brings people from all walks of life together and It’s the perfect way to get in the Holiday spirit! Afterward, walk on the beach, or grab a bite to eat at one of the many wonderful restaurants close by!

christmas parade on anna maria island
Photo from Shutterstock

Christmas Parade

The Christmas Parade is another event that people look forward to each year. If you have young members in the family, this event is a great way to get them excited about the holidays. They’ll be dazzled by the colorful floats and decorations passing by and are sure to feel the warmth and holiday cheer in the air. It’s a great way to make some spectacular holiday memories. The parade starts at the north end of the island and makes its way over to Coquina Beach!

Holiday Boat Parade

The Holiday Boat Parade is a truly unique experience. Locals from all over the area decorate their boats with lights and holiday decorations and make their way through the Sarasota Bay area. Onlookers gather on the Bridge Street Pier to take in the colorful show. This is another event that is suitable for all ages, and where people are able to come together to relax into the holidays and have a good time with one another.


Each winter season, residents and visitors gather at the Holmes Beach Field to partake in Winterfest. This festival offers a little something for everyone. You’ll find all sorts of vendors selling artwork as well as a plethora of other goods available for purchase. A large assortment of foods and refreshments are available for people to enjoy as well. While this event is family-friendly, there is also alcohol available for purchase. So, if you’re coming with young children be sure to keep that in mind. Best of all, you’ll get to soak up all that Winterfest has to offer to the tune of live music!

Christmas on Bridge Street

Christmas on Anna Maria Island wouldn’t be complete without ringing in the holiday season at Christmas on Bridge Street. This event is family-friendly and has something for people of all age brackets to enjoy. You’ll find everything from professional Christmas carolers in dickens era costumes to photos with Santa. There’s lots of hot chocolate to go around, too!

Are you ready to make the most out of your holiday season by treating your family to a getaway? If so, our Anna Maria property management team can help.

Mainsail Vacation Rentals offers comfortable, clean, luxurious vacation rentals suitable for couples and families. The majority of our rentals will sleep up to 6 people. For information about our current offerings, check out this page.

Do you own a property on Anna Maria Island? If so, we’re here to help you too! We’ll take care of all of the management aspects so that you can rent out your unit peacefully with minimal effort. To learn more about the benefits of offering vacation rentals, check out this post!


Mainsail Vacation Rentals
5325 Marina Drive,
Holmes Beach, FL 34217


Homes & Villas by Marriott International


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