Holiday Festivities in Anna Maria Island

Will you be home for Christmas, or are you planning to spend the holidays on spectacular Anna Maria Island? There are plenty of festive Anna Maria Island events you can enjoy. There are many wonderful places to stay in Anna Maria Island, so choose from our selection of Anna Maria Island vacation rentals, make your list of Anna Maria Island things to do for the holiday (and check it twice!), and come experience the holidays like never before.

If you’re heading off to warmer climates this holiday season, fear not: while he might ditch the heavy coat for a pair of Bermuda shorts and sandals, Santa DOES visit Florida just as anywhere else!

Annual Christmas Parade

Among the most popular Anna Maria Island events for the holiday is the early-December Privateer Annual Christmas Parade happening on December 11, 2021, at 10:00 AM. Since 1984, the Anna Maria Island Christmas parade has been bringing joy to both adults and children and is FREE of charge.

Starting at the north end of the island from Bayfront Park and traveling the entire length of Anna Maria Island to the south end at Coquina Beach, the parade features floats adorned as Santa’s sleigh, the pirate ship “Skullywag,” and other Christmas-themed trailers and boats with live bands, elves, and of course Santa himself! Candy and beads are tossed into the crowds lining the street along the way.

Once the parade stops at Coquina Beach, the fun does NOT end: there, you’ll find a huge party with hot dogs, pizza, soda, and chips, the opportunity for kids to meet Santa, and a gift for each child.

Learn more here.

girl at anna maria island tree lighting
Photo from Shutterstock

Christmas Tree Lighting

What’s Christmas without experiencing a tree lighting?

Head over to historic Bridge Street on Friday, December 4th for the decades-old tradition of lighting up the massive Christmas Tree erected each year. In the past, the lighting event has featured photos with Santa, Christmas carolers, and screenings of popular holiday movies such as “How the Grinch Stole Christmas.” In addition, enjoy a treat from the concession stands at the site!

Visitors and locals alike can enjoy the spectacle throughout the month of December: a reminder of the magic and mystique of the holiday season.

Learn more here.

Holiday Boat Parade

When you think “parade” you probably think about decorated floats and marching bands and cars, but what about a parade on the water?

The Holiday Boat Parade is among the most unique celebratory Anna Maria Island events of the year. Local boat owners dress up their vessels with holiday decorations and lights and set sail through Sarasota Bay. Watch from the Bridge Street Pier or the Longboat Pass Bridge as this festive flotilla passes by, ending at the Bradenton Beach Marina.

This year, the event will take place on Saturday, December 4th at 6 p.m. and last approximately 60-90 minutes. It is hopeful that up to 20 boats will participate in the parade, with a $200 cash prize for the best-decorated boat.

Want to be IN the parade rather than a bystander? There’s limited space on the Anna Maria Princess; check out the Bradenton Beach Marina website for details on how to reserve your spot. Space IS limited!


Outdoor events are much more abundant during the holiday season on Anna Maria Island as compared to many other places, so you can add the annual Winterfest to your list of Anna Maria Island things to do during the most wonderful time of year. The event is held at City Hall Field in Holmes Beach and will happen on December 13th and 14th from 10 AM to 4:30 PM.

This arts and crafts festival features art vendors, food, art courses, art exhibits, live music, and community booths. This is a great chance to support local artists and to possibly purchase a unique holiday gift for a friend or family member.

Enter a raffle to support the vendors and event, with proceeds used for the festival and art courses.

Parking and admission to Winterfest are free.

Find out more here.

Christmas on Bridge Street

Besides the annual Christmas Tree Lighting, what else can you expect in the way of holiday celebrations on popular Bridge Street?

Typically closer to Christmas, around December 17th – 19th or so, the street comes alive with performances by the Dickens Carolers (professionals dressed in period costumes), vendors selling handmade ornaments and other decorations, the smell of fresh-baked cookies, a hot chocolate bar, children’s crafts, and shops open later than usual. Santa might even be available in the park during this event!

You can win prizes, such as jewelry, gift certificates for local shops, or even massages on the beach, hotel stays, and so much more.

Don’t want to fight traffic and find parking? Take the free trolley to Bridge Street to join in on the fun!

Learn more here.

Anna Maria Island Restaurants Fit for the Holidays

Despite fully equipped kitchens found in most of our Anna Maria Island rentals, you just may want to take a break from cooking on Christmas. So, if you’re celebrating the holiday on vacation, you’ll find several area restaurants serving that day.

Some establishments open on Christmas Day include:

  • The Chateau Anna Maria: Located inside our sister property, Waterline Villas & Marina. Featuring a special holiday menu.
  • Bridge Street Bistro: Christmas lunch is being served! The bistro serves seafood specialties such as scallops, lobster tails, and fish & chips as well as burgers, filet mignon, and soups and salads. Lunch spot reservations being taken.
  • AMI Beach Café: Breakfast and dinner beachside buffets will be served Christmas Day. Breakfast choices could include eggs, waffles, French toast, and biscuits and gravy, with dinner choices consisting of platters, sandwiches, and wraps. Breakfast with Santa!
  • My AMI: French dishes, appetizers, and desserts are on the menu on Christmas Day! Get a taste of France for the holiday or ANY day!
  • Pier 22 in Bradenton: open 11 a.m. – 8 p.m. Christmas Day. Offers a holiday menu. 

Want to celebrate in your vacation rental but don’t want to cook? Harry’s Continental Kitchen in Longboat Key takes holiday dinner orders up to the 20th, which can be picked up on Christmas Eve.

In addition, holiday desserts such as cakes and cookies can be pre-ordered at Hometown Desserts or truffles and chocolates from Anna Maria Island Creamery and Bakery. 

Anna Maria Island restaurants serving dinner on Christmas Eve are The Chateau Anna Maria, Sandbar Restaurants, Bridge Tender Inn, Rod N Reel, and Waterfront Restaurant. Just off the island, you’ll find great Christmas Eve offerings at Bonefish Grill (Bradenton), Mar Vista Dockside Restaurant (Longboat Key), and Carraba’s Italian Grill (Bradenton).

Plan Your Anna Maria Island Vacation

If all you want for Christmas is sun, sand, and a home away from home, put Mainsail Vacation Rentals on your list and book one of our Anna Maria Island vacation rentals!

Your Anna Maria Island Rental

During the holiday season and throughout the year, Mainsail Vacation Rentals is sure to have the ideal Anna Maria Island rental to accommodate the entire family! Mainsail offers two- to three-bedroom Anna Maria condo rentals that sleep up to eight. You can enjoy stunning views of the Bay, state-of-the-art kitchen appliances, private balconies/decks, beach access, and so many other luxuries and accommodations such as hot tubs, heated pools, poolside grills, washer and dryer setups, flat-screen TVs, and provided linens and towels (including beach towels).