So much to admire on — and about — Anna Maria Island

Pine Avenue Restoration Project buildings feature shops on the ground level and guest houses on the second floor. –Ellen Albanese for The Boston Globe

ANNA MARIA CITY, Fla. — The thing Ed Chiles likes most about Anna Maria Island is the thing he hated most when he was a teenager spending summers here — there’s nothing to do. No amusement parks, no go-kart tracks, no malls. In fact, this sliver of land off Bradenton on Florida’s west coast seems lifted from an old-time postcard, when bicyclists owned the main street and ladies with parasols strolled the pier in the early evening to watch the sun drop into the ocean.

Protecting Anna Maria from the encroachment of retail chains and high-rise condos hasn’t been easy or cheap, as Chiles knows all too well. In 2007 he and two partners began buying up properties on Pine Avenue, Anna Maria’s de facto Main Street. Their goal was to turn them into old-Florida style mixed-use properties with boutique shops on the ground level and residences above. “You need a place to buy coffee or a newspaper,’’ Chiles said. “Small business is key, or you become another subdivision.’’

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As the project developed, Chiles realized he not only wanted to keep Anna Maria beautiful, he wanted to do it in an environmentally responsible way. That meant using energy-saving building techniques, replacing concrete sidewalks with crushed shell pathways, and landscaping with native plants. Today Chiles’s 11 properties along Pine Avenue have all been LEED-certified. At the other end of the street, the Anna Maria Island Historic Green Village, powered by solar and geothermal technology, generates more power than it uses, sending the excess back to Florida Power and Light. And the island has been cited as a model of sustainable tourism by the United Nations World Tourism Organization.

Groundbreaking? Definitely. But for most visitors, what really matters is that it all makes for an inviting and relaxing old-Florida experience.

Running a half-mile through the center of town, Pine Avenue connects the Gulf of Mexico to Tampa Bay. On the bay side, the 1911 City Pier still draws sunbathers and fishermen. Families enjoy the shallow, blue-green water, and anglers try their luck under the watchful eyes of patrolling pelicans. (The pier is temporarily closed as the city works to repair the damage from Hurricane Irma.) A free trolley service travels the length of the island from 6 a.m. to 10 p.m. daily — look for the green signs.

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It’s easy to identify Chiles’s Pine Avenue Restoration Project buildings: Look for the broad second-floor porches of the residences above the shops, which constitute the Anna Maria Guest Houses. Another clue is the sound of splashing and children laughing; each guest house includes a small heated pool in the back.

Among the diverse shops, many with expansive wood decks and outdoor seating, we visited Olive Oil Outpost, selling a range of gourmet food items from olives to charcuterie; Pineapple Junktion, a resale shop where we passed on a 1976 TRX auto for $17,000 and picked up some quirky greeting cards for a lot less; the Shiny Fish Emporium, with kids’ crafts and activities; AMI Outfitters, selling fishing gear, kayaks, and paddleboards; and Island Cabana, with clothing, home décor, gifts, and souvenirs.

Non-retail activities include the Anna Maria Island History Museum, furnished with artifacts relating to life on the island from the earliest settlers — the Tocobaga Indians — through the post-war settlements of the 1950s. Next door is the al fresco Anna Maria Jail, built in 1927. It’s said that once miscreants spent a night in the facility fighting off mosquitoes, they usually weren’t keen to act up again.

The Historic Green Village is a little difficult to find, but worth the effort for anyone who’d like to see a net-zero-energy complex, that is, buildings that produce more energy than they consume. The brainchild of British organic baby food entrepreneurs Mike and Lizzie Vann Thrasher, it’s a collection of five historic and new buildings, housing small local businesses, that use solar power and collect rainwater in cisterns under the parking lot. Go around the back of the general store to see a map, performance charts, and infographics about how energy and water are collected and saved. The Thrashers just happened to launch the Historic Green Village at the same time Chiles was spearheading the Pine Avenue Restoration Project; the combination of the two initiatives led developers and the local press to label Pine Avenue “the greenest little Main Street in America.’’

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The flip side of Chiles’s commitment to environmentally responsible building is his passion for local and sustainable food. In 1979 he bought the Sandbar restaurant, on the site of a 1912 bathhouse built to accommodate visitors who came to the island by ferry. “I bought my first beer here when I was 15 years old,’’ he recalls with a laugh. More recently he acquired the Beach House restaurant in Bradenton Beach and Mar Vista in Longboat Key.

The Sandbar sits on Instagram-worthy Anna Maria Beach on the Gulf end of Pine Avenue, soft sand edged with palm trees and sea grapes and blue-green water stretching all the way to the horizon. The menu includes organic produce from Chiles’s Gamble Creek Farm (think Seminole pumpkins and edible hibiscus blossoms), along with local fish, such as grouper, snapper, and bottarga, made from the roe of west Florida striped gray mullet. We tried appetizers of bottarga shaved over charred toast, moistened with olive oil – a clean, salty bite — and airy Seminole pumpkin blossoms stuffed with ricotta and goat cheese. As appealing as the food is, everyone takes a break to watch the gorgeous sunset on the beach.

Looking back on nearly four decades of honing a vision of Anna Maria Island for the 21st century, Chiles says, “This island reflects a character that’s intrinsic to its history and heritage and what its values are. And that’s sticky. If you lose that, you’re like every other place.’’

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