Serendipity is set to reopen in early November, inviting you to experience the island paradise of Anna Maria Island this winter. As you prepare for your stay with us, we’ve compiled a list of events that we’re most excited about this season.
December Events on AMI
Movies in the Park: December 5th @ 630pm
Starting on the 5th and going through the month of December, you can catch a holiday classic movie with refreshments every Wednesday evening, weather permitting. Hosted at the east end of Pine Ave near the pier in Anna Maria, this family-friendly event is sure to have you in the holiday spirit in no time.
Holmes Beach Tree Lighting: December 7th
Holmes Beach is holding its tree lighting ceremony and celebration this year on December 7th. This open house event will feature snacks, special shopping hours, and carolers.

Privateers Parade: December 8th @ 10 am
The yearly Privateers Parade is a local favorite. Hosted by a local pirate-themed charity group, the Privateers, this motorized parade starts at the Bayfront Park at @10am and ends at Coquina Beach.
Winter Wonderland in Bradenton: December 14th
Just take a short trip to the mainland and get immersed in a winter wonderland with seasonal fun for the whole family. This event features:
- Meet and Greet Pictures with Santa
- Holiday-themed vignettes, perfect for photos
- Roaming street performers
- Festive performances
- Free winter carnival games
- Local Vendors
But what makes this event truly unique and special is the evening snowfall, engineered to give the event a little extra holiday magic. It’s an experience you won’t want to miss!

Bonus: Disney Holiday Magic
Anna Maria Island is just a short drive from many theme parks, including Disney World! Give your Anna Maria Island stay some extra Disney magic during the holiday months and join Mickey & friends for a magical celebration, including a Christmas Parade, fireworks show, yuletide stage show, and character dance parties. The holiday celebration continues through the end of December, culminating in an extra special New Year’s Eve Celebration!
January Events on AMI
Anna Maria 6th annual Arts & Craft Show Jan11th & 12th
This two-day event takes place at City Field on Marian Drive near The Ugly Grouper in the heart of Holmes Beach. This event features over 50 local artists and vendors and a juried competition for artists in attendance.
Categories include:
- Ceramics/Pottery
- Accessories/Clothing
- Designers
- Digital Art
- Drawings
- Fiberwork
- Prepackaged Foods
- Glass Work
- Printmaking
- Jewelry
- Paintings
- Photography
- And so much more!
You are sure to find something perfect for yourself or your loved ones at this show.

Coquina Beach Art Show : January 18 & 19th
Still itching for some more art? Well, the Coquina Beach Art Show has got you covered. This show runs from 10 am-5 pm both days and features vendors, artists, food trucks, and live entertainment. There really is something for everyone!
Island Players – The Birthday Suite : Jan 9th-26th
Are you looking to take in a play during your stay on AMI? The Island Players present Birthday Suite, a comedy that will keep you laughing all night.
According to the Island Players Website, Birthday Suite is the story of “Four guests – for very different reasons -check into adjoining hotel suites where an unlocked door and an enthusiastic room waiter will lead to hilarious mistaken identities and misdirected infatuations.”
For your convenience, tickets can be easily purchased online here.
February Events on AMI
Florida State Fair: Feb 6th-17th
Who doesn’t love a fair? This day-trip-worthy event in Tampa hosts thousands of visitors bent on enjoying delicious fair food, mind-blowing rides, local exhibits, and wild entertainment planned for this week-long extravaganza.

Bradenton Area River Regatta: Feb 21st-22nd
This free event is packed with things to see and do. From stunt dogs to powerboat races and live music to a fan-favorite drone show, it is easy to see why the Regatta is such a favorite with locals. The highlights of this event are the Formula-2 and SST-45 powerboat races, with test runs at 10:30 am on Sunday, qualifying heats starting at noon, and final races at 2:00 pm and 2:45 pm for each bracket. For a full schedule of the event, click here.

These winter events on AMI offer a vibrant array of activities for everyone in your group. From engaging workshops to festive celebrations and community gatherings, there is something for everyone to enjoy. As we eagerly anticipate the winter season, we look forward to seeing everyone come together to create lasting memories with Serendipity. Contact us today to start planning your getaway to Anna Maria Island.
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