Explore Pine Avenue in Anna Maria Island

When you’re discovering Anna Maria Island, you’ll need to take some time to get your shopping done! You can find just about anything on AMI, from a trendy t-shirt to a souvenir shot glass, a unique antique, kids’ toys, and everything in between.

Luckily, Anna Maria Island has tons of special shopping spots that are different from anywhere else in the Sunshine State. You’ll have no problem finding something to remember your travels by!

During your time on AMI, you have to stop by Pine Avenue. This fun street in the City of Anna Maria is full of incredible shops and restaurants for you to discover, where you can get to know the local business owners and pick up something exciting to bring home with you! You’ll want to plan for at least an afternoon, if not longer, to find all the possibilities here. Read on to discover everything you need to know before leaving our Anna Maria rentals to visit Pine Avenue.

Getting Around

One of the best things about Pine Avenue on Anna Maria Island is the location. It’s right in the middle of some of the area’s most popular attractions, so you’re likely to pass it while you’re on your way to do something else. Just make sure you set aside some dedicated time to explore the shops and restaurants here! This is truly a family-friendly destination that you won’t want to miss out on amidst the other items on your itinerary.

You’ll find Pine Avenue in the City of Anna Maria, located on the north side of the island. The island is just seven miles long, so it’s always a quick trip to Pine Avenue no matter where your journey starts from. If you’re already in Anna Maria, you can easily walk to Pine Avenue. Otherwise, consider renting a golf cart or bike to get here, which can save you time and money compared to driving a car. For a budget-friendly option, you can also hop on the free Anna Maria Island trolley that stops all around the island!

Once you arrive on Pine Avenue, it’s easy to walk between the shops and restaurants. While you can drive here, it’s recommended to leave your car behind, since the parking situation is often less than ideal. Since the weather on Anna Maria Island is always sunny and bright, take advantage of the beautiful conditions and stroll through the streets!

Things to Do

The main appeal of Pine Avenue is the shopping. You won’t find your average big-name souvenir shops with the same t-shirts and hats as every other store. Instead, there are shops owned and operated by locals featuring unique souvenirs that you simply won’t find anywhere else. Whether you’re on a tight budget or you’re willing to spend a bit more cash, you can find something within your price range. Some of the most popular shops on Pine Avenue include Pink and Navy, The Island Cabana, and Libby’s Island Jewelry. You can find new clothes or a fun item for every member of the family!

You’ll also find several great restaurants up and down Pine Avenue, and they appeal to basically every palate. If you’re in the mood for Italian, check out Vinny & Cheryl’s Italian Kitchen for authentic Italian cuisine including pizza, pasta, and sandwiches. Wanting Mexican instead? Poppo’s Taqueria will be the spot for you, where all of their tacos, burritos, quesadillas, and other offerings are made with only the freshest local ingredients. Pizza Social is a new spot that’s popular with families, but if you’re in a hurry, you can head to J Burns Pizza to grab a slice from the take-out counter.

Need something to satisfy your sweet tooth? You don’t have to look far! Hometown Desserts is known for its wide range of freshly made brownies, cookies, cupcakes, and more. No matter what you’re craving, you can find it here! If you’re in the mood for a donut, you can come up with your own custom treat at The Donut Experiment. Start with a fresh cake donut and top it with whatever glaze and toppings tickle your fancy. You can go classic or be bold, allowing the whole family to create their own personalized dessert!


While Pine Avenue is known for being some of the best shopping on Anna Maria Island, that’s not all you’ll find here. Be sure to head to the Historic City Pier. This is a must-see attraction in the City of Anna Maria, as it holds tons of historical significance and played a large role in putting Anna Maria Island on the map. You can come to learn about the history of the pier, sample the locally caught seafood, and bring your fishing equipment and cast your line to try for the big catch!

One majorly popular area of Pine Avenue is the historic Green Village. This spot has been recently restored and is now entirely powered by renewable energy sources! Pedestrians are more than welcome here, and locals and visitors alike love visiting Green Village attractions like Beach Bums for equipment rentals and the Anna Maria General Store for all your beach picnic needs. 

Plan Your Vacation

Once you’re done exploring Pine Avenue and shopping until you drop, you’ll need a place to stay! Our Anna Maria Island rentals provide a comfortable, luxurious, safe, and affordable spot for your family to stay while you’re in town. You’ll have all the creature comforts of home within a unique beach-themed setting that reminds you of your beautiful surroundings. 

If there’s a history buff in your group, be sure to bring them to the Anna Maria Historic Society. Be sure to snap a picture at the former location of Anna Maria Jail, one of the area’s best spots for a photo op. You can learn all about the first settlers to AMI at the fascinating exhibits in the museum, and you’ll even see relics from years past. Stop into the Belle Haven cabin while you’re here. It fell into the bay in 1926, and after it was retrieved, it was restored and used as a home for many years.

Depending on what time of year you visit, you may even get to experience an event on Pine Avenue. The most popular event here is Food and Wine on Pine, which is typically held in early May. This annual event showcases the best art, food, wine, and music on the island and is perfect for the foodie in your group. Who doesn’t want to spend their days experiencing an upscale culinary event like this?

Where to Stay

We take pride in our unmatched customer service, so you can rest assured we’ll take care of you from the moment you book your rental to the last day of your stay. We’re proud to say many of our guests return to us year after year on their annual trip to Anna Maria Island! Each of our Anna Maria vacation rentals is meticulously maintained and designed with you in mind to give you an authentic Florida experience.