The phrase “Old Florida” means different things to different people.

Old Florida is a state of mind, a marketing tool, a romantic notion, a faded postcard tucked away in a shoebox in your grandmother’s attic. It's swaying palm trees, pink flamingos, enchanting mermaids, orange groves, desolate beaches, the color turquoise and a stiff tropical drink served in a coconut. It's pre-Disney — and, depending on who you ask, pre-air conditioning. It's a lonely highway exit, a weathered fishing village, a kitschy souvenir shop, an alarmingly cheap roadside motel. Old Florida is alive and well — you just have to look a bit harder these days to find it.

Nowhere else in the Sunshine State will you find spirit of Old Florida commingling with the new with as much (super-chill) zeal as in Anna Maria, a small city perched on the northern tip of a 7-mile-long sliver of sand of the same name. One of a handful of barrier islands or keys that stretch along west-central Florida’s famed “Suncoast” in the Gulf of Mexico, you’d be inclined to think that Anna Maria Island’s largest and busiest community, of which there are three, would be the city of Anna Maria.

Anna Maria Island, Florida

Built in 1911, Anna Maria's historic pier is a popular spot for fishing and dolphin-spotting. (Photo: Matt Hickman)

It’s not.

In fact, Anna Maria is arguably the sleepiest and, at just 1 square mile, smallest community on Anna Maria Island. Completely devoid of resort developments and strip mall-based amenities and with no bridge to mainland Manatee County to call its own, Anna Maria is the most secluded, and in turn, the most seductive spot on the island. There’s not much to do in Anna Maria — and that’s kind of the point.

And of the three cities on Anna Maria Island, low-slung and laid-back Anna Maria is the most emblematic of Old Florida while also being the most-forward thinking. Clinging on to a simpler, slower past but certainly not stuck in time, there’s almost a theme park-in-paradise quality to Anna Maria.

Anna Maria, Florida

A typical cottage, this one sporting a quote from "The Old Man and the Sea," along Anna Maria's main drag, Pine Avenue. (Photo: Matt Hickman)

A short street that's big on sustainability

Pine Avenue is where the marriage of Old Florida charm and 21st century sensibilities is the most celebrated in Anna Maria. Running east-west a half-mile through the center of town from the preternaturally pretty city beach (think: aquamarine water and generous expanses of powered sugar-esque sand) to the City Pier that’s jutted out over Tampa Bay since 1911, it’s hard to classify Pine Avenue as a proper “avenue” — it’s more of a sand-strewn, five-block-long main drag than anything. One can easily walk the entire length of it from gulf to bay in 10 minutes.

Pine Avenue’s fusion of eco-friendly new development and historic preservation may not be a big draw for sun-seeking out-of-towners and migrating snowbirds — admittedly, the street’s motto of “Preserving the Past, Embracing the Future” isn’t quite as alluring as the city’s motto of “Welcome to paradise without an attitude.” Still, it’s certainly the most fascinating aspect of this once down-and-out promenade reborn over the past decade as a “historic boutique business district.”

Headed by local restaurateur Ed Chiles (the son of the late, great folk hero-turned-Florida politician “Walkin’” Lawton Chiles), the $10 million Pine Avenue Restoration Project kicked off in earnest in 2007 when a grassroots campaign to transform largely neglected, low-traffic Pine Avenue from a ragtag collection of vacant lots and run-down 1940s-era beach shacks into a vibrant, walkable community was presented to Anna Maria’s then-mayor, Fran Barford.

Pine Avenue, Anna Maria, Florida

Pine Avenue: The "Greenest Little Main Street in America." (Photo: Bradenton Area CVB)

Not surprising for a small island community, the Pine Street Restoration Project was fiercely opposed by those pushing for Pine Avenue to be rezoned and redeveloped to be 100 percent residential. However, the vision presented by Chiles and co. ultimately won out.

To be clear, Chiles and his key project partners, investor Ted LaRoche and contractor Michael Coleman, didn’t set out to create what’s now referred to as the “Greenest Little Main Street in America.” Rather, everything came to together in a more holistic manner, a philosophy Coleman, who served as managing partner of the Pine Avenue Restoration Project, describes as “responsive development.”

Inspired by the exceptionally mustachioed co-founder of the Walkable and Livable Communities Institute, Coleman equates the Pine Avenue Restoration Project as a massive jigsaw puzzle with “one piece leading to the next piece.”

The ultimate goal of the Pine Avenue Restoration Project, a project that ultimately involved replacing concrete sidewalks with sandy pedestrian paths and swapping out water-guzzling turf grass with native plantings, was, in the words of Coleman, to be “practical, measurable and repeatable … otherwise you’re just showing off.”

In addition to completely doing away with asphalt in favor of softscapes, a total of 11 mixed-use buildings up and down Pine Avenue were erected in the place of empty parcels and long-abandoned buildings. A small handful of older existing buildings along Pine Avenue that had fallen into various states of dilapidation were also rehabbed and repurposed.

Pine Ave., Anna Maria, Florida

Pine Avenue's new mixed-use buildings typically consist of a retail business topped by a vacation rental unit. (Photo: Bradenton Area CVB)

While they’re obvious new builds, the Key West-style throwback structures, complete with nap-friendly front porches and pastel paint jobs, pay tribute to the vernacular architecture of the region.

Noted architect and Anna Maria resident Gene Aubry worked with the core of Pine Avenue Restoration Project team on the designs for the new buildings. Aubry also went on to serve as Anna Maria City Commissioner after voters ousted Harry Stoltzfus, scandal-prone sitting commissioner and lead crusader against the Pine Avenue Restoration Project, in a historic recall election.

Small town political drama aside, the ground floor of each “historically compatible” building built as part of the Pine Avenue Restoration project is home to a small commercial business.

Today, those businesses include typical beach town boutiques (think: handmade jewelry, nautical tchotchkes and Lily Pulitzer frocks) alongside eateries including a DIY donut joint where lines often snake out the front door and a family-run taqueria (it’s owned and operated by Coleman’s three sons) where organic and locally sourced ingredients dominate the menu. The second floor of each of double-decker cottage houses a vacation rental unit, the preferred mode of lodging in Anna Maria.

Pine Ave. Anna Maria, Florida

As part of a small business district-bolstering overhaul, asphalt and lawns gave way to sandy 'softscapes.' (Photo: Bradenton Area CVB)

While vacationers will no doubt be delighted to stay in a rental property that’s such a quick walk to the beach (and potentially located right above a top-notch taco joint), the buildings themselves are nothing to sniff at.

Boasting Platinum certification from the Florida Green Building Coalition, each structure is a showcase of green building technology revolving around Insulated Concrete Form (ICF)-based construction. This energy-efficient form of construction is also storm-resistant, an important consideration in a region that’s seen more than few significant hurricanes over the years. Vinyl hurricane windows, tank-less on-demand hot water systems and native landscaping (more on that in a bit) round up the green features of these exceptionally zipped-up neo-beach cottages.

Remarked Coleman following the 2010 certification:

“We have never been interested in the ‘points for marketing’ game, since our properties are not for sale. We do not believe in doing things just to score points on some arbitrary scale. However, we are committed to developing the best long-term solutions in terms of energy management, storm strength and water management. This begins with our Insulated Concrete Form wall systems, is furthered by our commitment to native landscapes and is completed with sand where pavers, concrete or asphalt ordinarily go. Our goal is to minimize our footprints, both physically and environmentally. It’s not so much ‘green’ as it is common sense stewardship which is part of our ‘responsive development’ mindset.”

Anna Maria, Florida

Pine Avenue's shady front porches are totally open for public napping. (Photo: Matt Hickman)

Historic preservation goes net-zero

In synchronicity with the Pine Avenue Restoration Project, another separate — but very much harmonious — green redevelopment project kicked off at the foot of Pine Avenue near the City Pier.

And it’s a doozy.

Spearheaded by British organic baby food entrepreneur Lizzie Vann Thrasher and her designer husband Mike, Anna Maria’s Historic Green Village is composed of a quartet of lovingly rehabbed historic buildings, some already existing on the current site and some relocated to Pine Avenue from other parts of Anna Maria Island.

Geared to “showcase recycling on a significant scale,” Historic Green Village’s core structures include the 2,000-square-foot Anglers Lodge (1913) which was moved from elsewhere on Anna Maria Island to its new home on Pine Avenue; the Rosedale Cottage (1914), an existing and very much in need of TLC building known by island old-timers as the Cozy Corner; the Pilsbury House (1917), a two-story beach cottage that had also fallen into serious disrepair; and the Sears House (1935), an original Sears kit home painstakingly moved via flatbed truck to Historic Green Village from its original Pine Avenue location in 2010.

Much like the energy-efficient buildings erected as part of the Pine Avenue Restoration Project, the diverse assortment of redeveloped historic structures (and token new structure) at Historic Green Village are now home to small, independent businesses.

Anna Maria, Florida

A 1935 Sears Modern Home sold via catalog is now a retail destination in Anna Maria's Historic Green Village campus. (Photo: Matt Hickman)

While this is all incredibly impressive, the Thrashers weren’t satisfied with just rehabbing and redeveloping a few forgotten old buildings.

Thanks in part to a 93.3-kW capacity photovoltaic array, geothermal heating and cooling systems, solar thermal panels, extensive rainwater harvesting scheme complete with massive underground cisterns and a host of other sustainable bells and whistles, both the Sears House and Rosedale Cottage were awarded with LEED Platinum certification in May 2012. What’s more, the entire Historic Green Village Campus is net-zero energy, producing more energy than it consumes. Working closely with energy expert Tom Stockebrand and engineer/LEED vet Ray Kaiser, the Thrashers achieved their goal in creating the first net-zero energy retail campus in the United States.

Reads the Historic Green Village website: “The ‘greeness’ of the HGV is unparalleled anywhere else in the USA and it is this aspect that makes it truly unique. By bringing together history and technology, we have tried to mingle the charm and roots of our buildings with the great American sense of optimism and energy that we, as British residents so admire. It is this spirit and energy that drives people forward, creating and recreating the future every time they encounter a challenge.”

Sleepy, unassuming and championing natural beauty over the built environment, Anna Maria is an unlikely location for one of the country’s most high-performance green building projects. Yet here it is, the sustainable crown jewel of a modest yet incredibly dynamic street.

Anna Maria, Florida

Roughly 400 rooftop PV panels power the net-zero energy Historic Green Village. There's also an EV charging station. (Photo: Matt Hickman)

Edible landscapes and a street you can eat

A merry mix of indie boutiques, galleries and cheerfully hued cottages, Pine Avenue revels in a folksy, unpretentious brand of Old Florida eclecticism. However, a short street boasting so much difference needs a common thread to tie it all together.

And that common thread would a series of over 30 lush planter boxes found up and down Pine Avenue. Filled with an array of tropical edibles ranging from collards to Chinese spinach to Ethiopian kale, the planter boxes are viewed as a sort of “teaching garden” in which visitors and locals alike are encouraged to sample the plants and, ideally, return home and give growing the plants themselves a go.

As mentioned, the Pine Avenue Restoration Project called for the removal of sidewalks, asphalt surfaces and grass lawns to make way for native species and truckloads of "250" sand. Heading up the initial effort and continuing to act as steward of Pine Avenue's landscape is polymath and Anna Maria resident Michael Miller. Having "escaped the prison of corporate politics" of his former career as an auto designer, these days Miller is mostly a landscape designer, native plant expert and philosopher.

A practitioner of what he calls “identity landscaping,” Miller explains that a landscape’s natural visual identity trumps aesthetics and that one should “landscape with natives and garden with exotics.” And while the visual identity of Pine Avenue, much like the rest of Florida, is dominated by coconut palm trees, Miller is quick to point out that they're non-native.

Anna Maria, Florida

Landscape designer Mike Miller shows off his tropical edibles in one of Pine Avenue's community gardens. (Photo: Matt Hickman)

“In the hierarchy of landscaping, ‘pretty’ is at the top of the list,” Miller told me on a tour of Pine Avenue while munching on a super-nutritious leaf of a moringa tree. “But identity, that’s number one.”

Miller created Pine Avenue’s five main edible gardens — the Merchant Community Gardens, as they’re officially called as each as sponsored by a Pine Avenue merchant — using information published by ECHO (Educational Concerns for Hunger Organization) as a key resource. Based in North Fort Meyers, ECHO is a nonprofit “information hub” that aims to alleviate world hunger by providing resources — seeds, included — to small-scale agricultural efforts in developing areas.

While a vacation home-heavy barrier island on Florida’s Gulf Coast is a far cry from the locales where ECHO normally dispenses assistance, Miller discovered that many of the tropical vegetables grown at ECHO’s Global Farm and Research Center could also be grown year-round on Pine Avenue. And, so in partnership with ECHO, Miller went about transforming Anna Maria’s sandy main drag into a locavorian wonderland and permaculture paradise.

It isn’t at all uncommon to find folks nibbling on the heat-tolerant tropical perennials and conventional seasonal varieties growing in abundance up and down Pine Avenue. For more civilized tastings, the bounty of Anna Maria’s street-side community gardens can also be found incorporated into dishes at Ed Chiles’ flagship restaurant located off the western end of Pine Avenue, the Sandbar.

Anna Maria, Florida

A Pine Avenue planter at Historic Green Village. Informative signs complete with QR codes explain what you're looking at. (Photo: Matt Hickman)

Situated right on the beach, the perpetually packed Sandbar seems an unlikely venue for esoteric edibles from a local community garden to appear. After all, it’s a crowd-pleasing seafood restaurant where the extensive menu is largely dictated by the needs of vacationing families and the leery palates of old-timers. This is the greater Bradenton area, not Brooklyn. There shouldn’t be any surprises — nothing too weird and nothing too fancy.

But there are surprises and Chiles, at every opportunity, make a point to showcase sustainable farms and heritage seafood producers at the Sandbar and his other two “Old Florida-style” eateries, the Beach House Restaurant and Mar Vista Dockside Restaurant and Pub. Key farm to fork/tide to table partners include Gamble Creek Farm, a 26-acre hydroponic farm in rural Manatee County; Two Docks Shellfish, a local father-son producer of Sunray Venus clams; and Anna Maria Fish Company, an artisanal bottarga (cured grey mullet roe) purveyor that sources from Cortez fishing village, a National Register of Historic Places-listed site that's successfully managed to stave off encroaching development over the years and remains one of the last surviving working fishing villages on Florida's Gulf Coast.

Wild boar, trapped and processed at a bison ranch just south of Sarasota, also recently debuted on the menus at the trio of Chiles-owned restaurants. Again, longtime Sandbar patrons will likely stick with what they know —grouper sandwich, grilled, hold the tomatoes, and the lady will have the coconut shrimp salad — but more adventurous diners will be rewarded with fare like wild boar stew with micro cilantro and cannellini beans.

Wild boar stew? Now that's Old Florida.

Pine Avenue, Anna Maria, Florida

One of the top attractions in Manatee County, Anna Maria's historic pier sits at the foot of Pine Avenue. (Photo: Bradenton Area CVB)

Your non-private private island awaits

Despite its alluring remove that suggests you have to board a ferry or rent a private seaplane to get there, Anna Maria is highly accessible: the beach is an easy 40-minute drive from Sarasota-Bradenton International Airport (with its water features, pink flamingo displays and Eames Tandem Sling seating, SRQ is the gateway to Old Florida). The larger — and far less charming — Tampa International Airport is a bit further off.

And once in Anna Maria, there’s little need for a car as pretty much everything (the beach, bars, ice cream, flip-flop emporiums, etc.) is within walking or biking distance. For excursions elsewhere on the Anna Maria Island, a free trolley runs the entire 7-mile stretch of the island from Anna Maria City Pier in the north to Coquina Beach in the city of Bradenton Beach on the southern end of the key. Two bridges connect Anna Maria Island to the mainland: Cortez Bridge via Bradenton Beach and the Manatee Avenue Bridge via Holmes Beach, the island’s most populated and most built-up (but really not all that built up at all) community. Kayak is also a popular mode of transportation.

Vintage postcard, Anna Maria Florida

Presenting the real Old Florida: A 40s-era postcard depicting Anna Maria. (Photo: Boston Public Library/flickr)

While Anna Maria still easily qualifies as a hidden gem, the hidden part isn’t quite as pronounced as it used to be. People — many seeking authenticity and a marked change of pace from Florida's often hectic, high-rise-studded beach "scene" — are on to this cozy coastal village.

Anna Maria Island’s pristine gulf beaches have won high praise in recent years from publications including Southern Living and Conde Nast Traveler. The city of Anna Maria has also, not surprisingly, been singled out as a primo spot to experience a genuine slice of Old Florida while Pine Avenue has received a different kind of recognition by the United Nations as a case study in sustainable tourism done right. Ed Chiles continues to garner attention throughout the region for his championing of small, local producers.

A place where the Florida of yesteryear has been both romanticized and rebooted, preserved and puffed, no one quite does old — and new —like Anna Maria.

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Matt Hickman ( @mattyhick ) writes about design, architecture and the intersection between the natural world and the built environment.