By Vanessa Caceres

On Anna Maria Island’s Pine Avenue, you’ll get an Old Florida feel. You can shop, eat, discover a little local history, take a snooze in colorful Adirondack chairs set up outside local businesses, and even fish and catch some waves—all within less than a mile. 

Pine Avenue begins on a tranquil Gulf beach and continues to the Anna Maria City Pier, where fishing is available 24/7 within view of the Skyway Bridge spanning Tampa Bay.

You don’t want to miss the great eating, sightseeing and shopping between the beach and the pier on Anna Maria Island. Many of Pine Avenue’s businesses use environmentally-friendly practices (it’s called “The Greenest Little Main Street in America”) and support other local merchants. Here are 10 must-sees on Anna Maria’s Pine Avenue, with a focus on the street’s food and sightseeing highlights.

1. The beach

Start your visit on breezy Anna Maria Beach, where Pine Avenue begins. Get some sun, bring a picnic or take a dip in the Gulf waters. If you’re lucky, you’ll see dolphins or even stingrays. If you visit on a Sunday morning between 10 a.m. and 1 p.m., you can catch some rays while you listen to the soothing jazz sounds from the Sunday brunch at The Sandbar Restaurant, a beachside eatery. You might also smell the sweet aroma from your next destination wafting toward you. 

2. Anna Maria Donuts

At Anna Maria Donuts, sidle up to the hot donut bar and select your icing and then your toppings. Rainbow and chocolate sprinkles? Check. Bacon? Check. Crushed oreo cookies? Check on that one, too. Bradenton resident Judy Vobroucek says she frequently brings out-of-town guests, especially kids, to Anna Maria Donuts. She once took a niece to watch the sunrise on Anna Maria City Pier and then got her donuts. “We took our donuts and drinks to the beach,” she says.

3. Poppo’s Taqueria

In the same quaint shopping plaza that houses Anna Maria Donuts, you’ll find Poppo’s Taqueria. Here you can choose fillings like tempeh (a soy product similar to tofu), honey lime slaw, feta cheese and red onion, in addition to the more traditional rice, beans, beef and chicken. Poppo’s also offers locally-sourced grass-fed bison as a filling. None of the restaurant’s soda choices contain high fructose corn syrup, and the owners use organic produce whenever possible.

4. Anna Maria community gardens

Want to try Okinawa spinach, edible hibiscus, moringa and other exotic-sounding vegetables? They’re yours for the taking in the edible boxed gardens located outside eight (and counting) Pine Avenue destinations. Each box has an information card and a scannable QR code. One goal is for the businesses supporting the gardens to incorporate the veggies into their recipes, says landscape designer Michael Miller, a local resident who helped install the gardens. Another goal is for residents and visitors to try the vegetables they are growing. “People can taste them while they’re standing there,” says Miller.

5. Olive Oil Outpost

Foodies, take note. Snowbirds, locals and tourists all come to Olive Oil Outpost to try its oils, balsamic vinegars, pastas, cheeses, olives and wines. Get ready to sample lemon olive oil, jalapeño olive oil and other gourmet delights (like baklava) available for sampling on a given day, says Thomas Aposporos, who works at the store. The store also sells local honey and Italian bread; it’s located right next door to the Spice Merchants, so you can season anything you buy from Olive Oil Outpost with global spice offerings.

6. Anna Maria Jail

Make sure to get your picture taken at the Anna Maria Jail. No longer functioning as an actual jail, this tiny, open-air square building was built in 1927 mostly as a measure to get a temporary hold on rabble-rousers visiting Anna Maria Island for weekend partying. Once miscreants spent a night in the facility and were attacked by hundreds of mosquitoes, they usually weren’t keen to act up again. Have a hankering for a little more local history? The jail is located right next door to the Anna Maria Historical Society Museum and Park.

7. Hometown Desserts

The coconut cake, carrot cake and key lime pie, among other offerings, at Hometown Desserts are so delectable they’re sold at more than 10 local restaurants and shops. Owner Cindy Tutterow had been baking her desserts wholesale for weddings when she decided to open a storefront in 2012. Thanks to the influx of tourists who come to her shop, she’s even shipped orders out of state, and Hometown Desserts has also been featured in Southern Living magazine.

8. Vinny & Cheryl’s Italian Kitchen

Look in the window of Vinny & Cheryl’s Italian Kitchen, and you can see what breads are on the menu for a given day. The owners change the menu daily, but Italian favorites like veal parmesan, baked ziti, lasagna and pizza are usually part of the mix. The kitchen has only a few chairs for eat-in customers, but it does a bustling take-out business.

9. Relish Café & Marketplace

Relish Café uses tomatoes from a farm in nearby Bradenton, and it sells frozen popsicles from a Sarasota operation called Pop Craft. Fresh fruit waffles, chicken salad and the protein breakfast burrito are some of the café’s most popular dishes, says employee Brenda Circharo. Relish is located in Anna Maria’s Historic Green Village, an eco-friendly structure. In fact, the café relies mostly on solar power for its energy, and it also uses and sells a number of recycled products.

10. Anna Maria Pier

Although technically not on Pine Avenue, you can’t miss the pier if you’re exploring Pine. Take a walk on the pier to spot herons, pelicans, fish, dolphins, tourists from around the world and lots of people fishing—just don’t let them knock you over when they land their catch. If you’re lucky, you might watch someone reel in a large shark. The pier is open 24 hours for fishing, and you’ll get a different slice of life (not to mention a panoramic view) by visiting different times of the day.