The Festive AMI Traveler’s Guide to Celebrating Christmas and New Year’s

There is no better place to spend the holiday season than Anna Maria Island. Sure to be your home away from home for the holidays, our community is full of festive ways to celebrate during your stay. From parades sure to lift your holiday spirit, to local shopping boutiques transformed into winter wonderlands, there is something for everyone on the island. We have put together a festive AMI traveler’s guide that includes some of the most popular events happening on and around the island to help you spend your time from Christmas through the New Year. 

Getting Into The Christmas Spirit on Anna Maria Island 

AMI Chamber Tree Lighting & Holmes Beach Holiday Open House

Hosted on Holmes Beach, join the community as we get ready to celebrate Christmas with the annual tree lighting and holiday open house. This yearly favorite event for locals features the Crosspointe Fellowship Band singing holiday tunes, local charity group the AMI Privateers hosting Santa’s Sleigh, and local businesses joining in by staying open late for holiday sales! Tasty treats will also be available.

Holiday Shopping with the Coquina Beach Market

Shop small and shop local for all of your gifting needs at the Coquina Beach Market. This market is open Wednesdays, Fridays, and Saturdays In December and January. It is no secret that we love our local markets, and we are sure that you will too. Support local artists and get gifts for everyone on your holiday shopping list, including yourself.

Christmas Glow Run 5K

In neighboring Sarasota, the Christmas Glow Run 5k is sure to be an unforgettable holiday experience. Colorful Christmas lights decorate the race and it is accompanied by lively music. Glow products are complimentary with registration to help you light up the night. Connect with friends and family and watch their progress with an integrated app. But the best part? Cross the finish line with a magical snowfall shower to create even more holiday memories. 

Christmas on Bridge Street

Historic Bridge Street is transformed into a Winter Wonderland with Christmas decorations, holiday music, and more. The centerpiece is a giant lit Christmas tree. Live entertainment, kids’ zones, shopping, dining, and more make this one of the community’s favorite places to celebrate the holidays. 

Christmas in the Garden at Longboat Island’s Chapel

This ongoing festival event spans the month of December and features festive lights, Christmas Trees from local businesses, and special performances by local musicians. Wander the peaceful gardens that have been transformed into a Winter Wonderland. This is an especially magical experience for families and visitors of all ages and backgrounds. The best part? Admission is free! 

Bradenton Winter Wonderland 2025

Wander through downtown Bradenton as it is transformed from Olde Florida Charm to a snowy winter wonderland. You read that right, snow! This festival features Mr. and Mrs. Claus for photo opportunities, holiday-themed vignettes, performances from local youth choirs, roaming performers, and local vendors for unique holiday gift shopping. 

MindTravel Live-to-Headphones Silent Piano Concert – Manatee Beach

This unique musical experience is coming to Manatee Beach for the first time, right in time for the holiday season. According to their event page, attendees “Slip on wireless headphones and be transported by MindTravel’s signature live-to-headphones “silent” piano journey. Composer and pianist Murray Hidary creates an unforgettable evening of soothing, improvisational music designed to quiet the mind, open the heart, and connect you more deeply to yourself and those around you.” This is sure to be an unforgettable night of music and beauty. 

Christmas at the Drift

Hosted by the local charity group, the AMI Privateers, join in the fun as The Drift hosts its annual Christmas Celebration, complete with raffle items, live music, and a holiday buffet. Proceeds to go towards funding the AMI Privateers Drift In Scholarship that supports local children and the building events within the community. 

Take a Class on Mixology to Summon the Holiday Spirits

Have a love for holiday movies and looking for a way to really get into the spirit of the season? Hosted by Anna Maria Island’s own Gulf Coast Bartender Co., you can learn to mix your own holiday drinks based on some classic holiday films. With a series of mixology classes throughout December based on favorites like Christmas Vacation and A Christmas Story, this is a perfect way to spend an evening and give new life to your favorite holiday films. Sure to be a fun time full of laughs and festive fun. 

Open Studios Night HOLIDAY EDITION

Looking to celebrate the holidays and take in an evening of art? Artmostphere’s Open Studio Night is just the right fit for you! Hosted in neighboring St. Petersburg, FL, this festive evening is dedicated to art, community, and local creators. According to their event page, you can expect resident artists to open their studios, share their newest work, and welcome you into their creative world. This is a wonderful opportunity to shop local art and meet artists while connecting with the creative community. Local art, after all, makes some of the best holiday gifts, and no one would blame you for picking out a little something for yourself as well. 

Blizzard Bazaar: St. Pete’s Coziest Holiday Market

Another event in the neighboring St. Petersburg, this holiday market is sure to be unlike any other you have been to before! The market boasts over 50 vendors all set up in a winter wonderland set in a ski lodge that will take you back to a simpler time. Be ready for Christmas lights, delightful photo-ops, some time with Santa, and even snow!

The $5 admission fee includes

• 50+ Curated local vendors
• A Christmas Tree Farm presented by local sponsors
• Snow flurries throughout the night
• Meet and Greet with Santa
• Full festive bar with themed cocktails
• Holiday music and lights

Fresh Wreath Workshop at Mezzo Market

Feeling creative and want to craft some holiday magic for yourself or a loved one? The Fresh Wreath Workshop at Mezzo Market might just be the right outlet for you. Learn to make your own fresh wreath under expert guidance in this perfect event for family, friends, and individuals. You will be provided with all the materials needed to craft your own beautiful, unique wreath to take home. No experience necessary! 

Sarasota Art Museum After Hours featuring Strings of the Season

The Sarasota Art Museum hosts an evening of after-hours magic of seasonal music that will have you waltzin away the night as string musicians play well-loved classical music. This event features extended hours in the galleries, shop, and bistro, as well as dancing. 

Get Ready to Ring in the New Year 

Looking for the best way to ring in the New Year? From glamorous galas to quiet beach escapes, there is no shortage of celebrations to attend in the surrounding areas of Anna Maria Island. Below are a few of the events available to attend to ring in 2026. 

A Coastal Countdown: New Year’s Eve at Oshen 21+

Looking to celebrate the new year in style? The New Year’s Eve party hosted at Oshen, located at The St. Regis Longboat Key Resort, promises to be an evening of unparalleled elegance, opulent culinary delights, and entertainment that you won’t find anywhere else. You’ll be mesmerised by the beautiful Gulf waters as 2025 is washed away and you are whisked into 2026. 

The St. Regis Bar Met Gala NYE Event

The St. Regis Bar hosts New Year’s Eve this year in the glamorous style and spectacle of the Met Gala. This exclusive VIP event will have you feeling like a celebrity as you take in the avant-garde fashion, curated cuisine, and overall artistry inspired by the theme. Tickets for this event  sell out quickly, so make sure to secure yours before it’s too late. 

Westin Sarasota New Year’s Eve Soirée

The Westin Sarasota hosts its annual New Year’s Eve party, this year reimagined with lush greenery, cascading florals, and a lavish rooftop buffet. This rooftop celebration features a DJ, a lively dance floor, party favours, and a complimentary champagne toast at midnight. 

MOONLITE NYE: The Gatsby Gala | 21+

The Floridian Social celebrates 100 years with a night of live performances, music, champagne, and more, all set to the theme of the roaring ‘20s. Patterned after the opulence of Gatsby himself, you’ll be transported to a bygone era through one of the most glamorous New Year’s Eve celebrations the area has to offer. This one is sure to be a night to remember. 

New Year’s Fireworks on the Island

While there are no official fireworks planned for Anna Maria Island, countless displays are visible from all over the island on New Year’s Eve. Camp out on the beach, or pour yourself a glass of champagne from the comfort of your vacation rental. This is one of our favorite cozy ways to ring in the New Year. 

Serendipity is ready to help you spend your season in your new holiday home away from home. Contact us today to start planning your stay in one of our luxury homes on the beautiful Anna Maria Island.