Experience the “Old Florida” Feeling On Anna Maria Island

Vacation is supposed to be a time when you can relax, rest, and unwind, but these days, it’s becoming harder to do that. Everywhere you go, it’s so tempting to still be connected to your phone or catch up on one last work email.

It’s hard to find a vacation destination that allows you to unplug and experience the calmer conditions of days gone by.

Anna Maria Island

Fortunately, there is still a place where you can experience that slow-paced “Old Florida” feeling: Anna Maria Island. Here, you won’t find a ton of high-rises or chain restaurants. Instead, you’ll see vacation rentals that blend in with the residential homes and cafes and restaurants that are locally owned and incredibly inviting. Let’s dive into how Anna Maria Island has managed to maintain that “Old Florida” feeling forgotten by so many.


Anna Maria Island history is truly fascinating and is something you should explore a bit when visiting. AMI was first inhabited in 1000 AD by the Timucuan and Caloocan Native American tribes. They lived in peace for over 500 years until explorer Ponce de Leon arrived in 1521 and claimed the land in honor of Maria Anna, who served as Queen next to King Charles II of Spain.

Fast forward about 300 years when the first permanent settlement was created on the Island, called the city of Anna Maria. This city was founded in 1892 by George Emerson Bean, who made his home on the portion of Island that is today known as Bean Point. It took awhile for the rest of the Island to gain permanent settlements, but the south side of the Island known as Bradenton Beach was officially formed in 1953. Before Bradenton Beach was established, it was quite hard to get from Anna Maria Island to the mainland and back. When the Cortez Bridge was built in 1921, travel became a lot easier. More people started moving to Anna Maria Island permanently.

While you’re on Anna Maria Island, several fascinating historical sites put the stories into perspective. Visit the Anna Maria Historical Society to view an old jail that used to serve the Island, or head down to Anna Maria City Pier, an island staple for more than 100 years.

old Florida map

Buildings and Structures

One way Anna Maria Island keeps its old-time feeling is by its emphasis on community. In many vacation destinations, especially in Florida, you’ll find high rise after high rise along the shore, interspersed by big chain restaurants or well-known souvenir shops. However, in Anna Maria Island, it’s precisely the opposite. The vacation properties on the Island tend to blend in with the residential homes, so nothing stands out or looks too touristy. On the same note, you won’t find a ton of busy chain restaurants. You can get a personalized experience from the friendly locals that own their own mom-and-pop eateries.

Anna Maria Island maintains the Old Florida feeling; it’s not uncommon to see buildings only 10, 12, or more stories high in the sky. There are no buildings taller than three stories tall on Anna Maria Island. This restriction helps the Island maintain that relaxed feeling and ensures that you have an uninterrupted view of the ocean no matter where you are.

man and woman casual dining

Casual Atmosphere

Anna Maria Island’s old Florida charm also contributed to its casual and family-friendly atmosphere that allows you to sit back and unwind. All too often, a vacation that is intended to be slow-paced and relaxing winds up being packed full of activities that keep us busy. This is not conducive to relaxation. Anna Maria Island is a place that emphasizes moving slowly, allowing you to truly enjoy every experience.

Picture a place where you can stop and chat with the locals, let your kids ride bikes, or run around in the yard while you sit back by the pool. You could even (gasp!) leave your phone behind in your Anna Maria Island vacation rental while you head out to the beach. This picture is a reality on Anna Maria Island. You don’t have to pack a bunch of fancy clothes to try to impress anybody at dinner. Most restaurants on the Island, you’ll be just fine coming as you are in your jeans and t-shirt.

All in all, Anna Maria Island allows you to have your vacation exactly as you want. Would you like to sit by the pool all day or explore the natural sites in the area without rushing to attractions? Go for it! Would you rather experience exciting watersports and a romantic dinner with your sweetheart? You can do that, too! It’s all up to you, and there’s no one around to judge you or tell you about a different activity that you “should” be experiencing. In Anna Maria Island, a vacation can be what you want it to be.


One of the best ways to get in touch with Anna Maria Island’s Old Florida charm is indulging in the local artwork. Take the time to see a show, or stop by a local art gallery to talk with the best regional artists. Head to a one-of-a-kind souvenir shop to pick out a handcrafted piece of jewelry or home decor to take back with you.

For instance, if you’re interested in a piece of artwork that perfectly captures the island lifestyle, heading to Bob Brown Art in the city of Anna Maria. You can find more whimsical works at Emerson’s Studio Store or visit J. Lazzara Gallery for a wide variety of sculptures, paintings, mosaics, and more. Witnessing these incredible pieces of art and speaking to the talented individuals responsible is one of the best ways to get a unique perspective on what life on Anna Maria Island is truly like.

Plan Your Visit

For your next trip, consider a stay in one of our Anna Maria Island rentals! Our wide range of vacation rentals includes our one- to two-bedroom rentals, perfect for solo travelers, couples, or smaller families, as well as our three- to four-bedroom AMI rentals for bigger groups. Contact us today to learn more!

But “the arts” doesn’t just have to be about visual arts like paintings and sculptures; it can also be about the performing arts.

If you want to see a unique show while you’re in town, be sure to stop by The Island Players. This group and playhouse have been an island staple since 1949 and has been identified as a Florida Heritage Site. They typically perform five or six different plays within a season, so there’s sure to be something unique and entertaining going on while you’re in town. Coming out to a play is a wonderful way to get your family out of your vacation rental and experience a great show that doesn’t take place on a screen.

You deserve a vacation where you don’t have to worry about everything going on back home or always feel overwhelmed by the sheer amount of people and activities around you. Anna Maria Island provides all of that and more.