Anna Maria Island: The Perfect Winter Vacation Getaway

With the holidays just around the corner, find out why people are flocking to Anna Maria Island for the perfect winter vacation getaway.

Are you planning a winter vacation for your family? Are you searching for a place that offers numerous activities? Do you want to go somewhere that gives the right amount of cold without worrying about any snowfall?

Then the state of Florida is your best bet. Florida recorded over 126 million visitors in 2018. Tough most of them came to have fun in the sun, there is a gem that you need to experience during winter.

You need to visit Florida’s Anna Maria Island.

Beach and outdoor enthusiasts named Anna Maria Island as one of the best islands in the world. But what does the island have to offer during winter? 

Continue reading below and discover what Anna Maria Island has to offer.

A Trip to the Museum

If you are taking your kids to Anna Maria Island, make sure to drop by the Historical Museum. The structure is an old 1920s icehouse that the city transformed into a museum. It houses numerous exhibits that show the island’s evolution.

Here, you will learn the story of the island’s first settlers. You will also get a glimpse of the island back when it was still an Indian fishing camp.

The museum is full of photos and other artifacts. Make sure to take a photo in the ruins of the Old City Jail that dates back to 1927.

Enjoy Some Music in the Park

Do you love jazz and Rumba music? Then head on to the Mosaic Amphitheater at the Bradenton Riverwalk for some great music in the park. 

Here, you can spread your blankets on the ground and set up a picnic. You can also buy food and craft beer in the area. The proceeds of the purchases will go to Realize Bradenton, a local non-profit that helps develop the community. 

The free concerts start at 6 pm every Friday.

Another great option is the Annual Anna Maria Jazz Festival. Various groups play different tunes celebrating the island’s love for jazz over the last 70 years.

Join the River Regatta

If you love boats you will certainly enjoy the Bradenton Area River Regatta. Boat-owners will pit their boats in a Formula 2 boat racing competition. 

While watching the boats race, you can enjoy live free music. There are also kiddie activity zones and spectacles like dog stunt shows.

Don’t worry about the food as there are food trucks and stalls around the area. To cap off the day, you can watch beautiful fireworks fill up the night sky.

Art Appreciation

In case you love art, you need to visit the Holmes Beach Art District Art Walk. The Art Walk features local artwork coming from the creative people of the island and nearby areas.

The artworks come in various forms. These include mixed media and acrylic paintings. They also feature wildlife and landscape photography.

You will also see some of the finest in local glass and pottery. Like in the other events, expect to hear live music and some complimentary refreshments.

Furthermore, there is the Annual Winterfest. The event also takes place in Holmes Beach. It caters to the island’s young artists.

Here, you will see budding artists competing. 

The Historic Bridge Street

Anna Maria Island is famous for its white sandy beaches and turquoise waters. It is a place that embodies the old charm of Florida. You'll get to see that old charm at the historic Bridge Street.

You will find the Bridge Street right at the southern tip of the island. The area is a perfect spot to eat, drink, and unwind.

It is also home to some boutiques, galleries, and souvenir cottages. You can also hang out in some of its nearby bars and restaurants. If you have a knack for fishing, you may also catch some if you want.

If you are visiting in December, stop by the area and celebrate Christmas on Bridge Street. Here, you will see performances from the Dickens Carolers. They sing tunes from the Rowlett Children’s Choir. 

Beach Fun

A trip to Anna Maria Island is incomplete without visiting the beach. As one of the least snowy places in Florida, the island lets you stroll along the shoreline without stepping on any snow.

Go for a day trip to Bradenton Beach. Ride the trolley and enjoy the sights of the breathtaking Gulf Coast.

You can explore the different fishing piers and white sand. You can also check out the different shops and grab a bite from any of the local restaurants.

Make sure to take a dip at the beach. You may also join a fishing tour to experience the island’s love for fish.

Cocktails Galore

With the cold weather, winter on the island is an excellent time for a cocktail tour. The island is full of several drinking spots.

There are high-class drinking places, as well as laid-back sports bars. But if you want something that offers unique concoctions, drop by The Doctor’s Office on Holmes Beach.

Experience the Boat Parade

The Holiday Boat Parade is one of the most anticipated events on the island and the highlight of any winter vacation. This is a time when locals showcase their lighted boats. They surround the Sarasota Bay Area as locals and tourists watch.

The Lighting of the Tree

Last but not least, you and your family should witness the annual lighting of the Anna Maria Island Christmas Tree. This is an event that brings both locals and tourists together.

Usually, they place the Christmas Tree near Bridge Street’s roundabout. This is close to the Bridge Street Pier where you can catch the lighting ceremony.

Sometimes, the event also features a special screening of a Christmas-themed movie. The tree will be up for the entire month of December. 

Experience a Wonderful Winter Vacation!

Now that you have more than enough reasons to enjoy a winter vacation getaway in Anna Maria Island, you need to start planning right now. But if you wish to visit the island at any time of the year, we will gladly help you out with your accommodations. 

Feel free to get in touch with us. Let us know your plans and let us arrange your reservations. We offer some of the finest rooms and the best rates the island has to offer.

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