Visit Pine Avenue in Anna Maria Island

When you are staying in one of our many beautiful Anna Maria Island vacation rentals, you’ll want to take the time to visit Pine Avenue. Pine Avenue is a fun and exciting street in Anna Maria that offers various restaurants and shopping to explore.

You can spend an entire day discovering what this main island downtown area has to offer. 

three women window shopping

Getting Around

Pine Avenue is located on the north side of the island. The entire island is only seven miles long, so getting to Pine Avenue is simple. Anna Maria Island has many bike or golf cart rentals for you to take advantage of. Anna Maria also has a free trolley that makes stops all throughout the island. The Anna Maria Island trolley operates from 6 a.m. to 10:30 p.m. each day.

Pine Avenue begins on a beach and continues all the way to the Anna Maria City Pier. This stretch offers a wide variety of activities to make anyone happy. The beautiful gulf beach has plenty of space to relax, play, or fish. Anna Maria City Pier also offers gorgeous water views, with chances to spot wildlife, like dolphins, stingrays, pelicans, or even sharks.

Things to Do

Anna Maria Donuts has a hot donut bar where you can choose from a wide variety of toppings for your donut. For lunch, make a stop at Poppo’s Taqueria. This taco shop offers delicious tacos with fresh ingredients, locally sourced meat, and organic produce. Vinny and Cheryl’s Italian Kitchen serves favorites for dine-in or take-out service, to bring back to our Anna Maria Island vacation rentals, on Pine Avenue. You can take your meal to the beach with your friends or eat at one of their intimate tables. For dessert, stop by Hometown Desserts. This bakery serves delectable classics like key lime pie, carrot cake, and coconut cake. It has become so popular over the years that it has been featured in Southern Living Magazine. 

Plan A Visit

Beautiful Anna Maria Island beachfront rentals are available for your stay on the island. If Pine Avenue sounds interesting to you, there are various beachfront vacation rentals for you to choose from. Choose one that suits you and your needs, and you will wake up every morning to the stunning beach sunrise and go to sleep every night to the sounds of the ocean. 

women's clothing in store


Alternatives to Anna Maria Island shopping are a wide variety of shops to peruse on Pine Avenue. The Island Cabana is a wonderful boutique that sells fashionable clothing and accessories for women. It also has memorable souvenirs and gifts to buy for those at home. If beachwear is what you need, head to Beach Bums Recreational Rentals & Gift Shop. They have all the beach gear you could want or need, plus jewelry, mugs, hats, and more. At the Shiny Fish Emporium, you’ll find unique handmade gifts, like hand-painted sand dollars and mini surfboards. Lastly, and a must-stop place on Pine Avenue, is The Olive Oil Outpost. Not only do they sell fine olive oils, vinegar, pasta, cheeses, and wines, but they do tastings too!

We recommend you head to the Anna Maria Island Historical Society Museum Complex to learn more about the island. Simply visit the museum building, or take one of their walking or biking tours of the Island for something more personal. 

For another historical stop, head to the Anna Maria Jail. While jail may not seem like the greatest place to visit, it is a historic spot on the island. This jail is no longer functioning and boasts an interesting history.