Framed by picture windows showing traffic on Osprey Avenue, Metro Café’s customers on any given evening represent a smattering of Sarasota demographics: the retiree social circle finishing up an afternoon coffee klatch; the middle-aged business folk grabbing a glass of wine before dinner. And over in the corner, pulling together chairs and tables to accommodate everybody, is the newest blip in the local census: the stylish, young, successful crowd—drinking beer, eating quesadillas and weighing their options. It’s a Friday night in downtown Sarasota, and these kids are just getting started.

The group includes an assortment of familiar last names, the children of notable Sarasotans, among them Kelly Kirschner, 32, son of a former Sarasota mayor and a newly elected city commissioner himself, and Andrew Foley, 25, one-half of the wunderkind sibling team now running Sarasota News & Books, whose developer father began the downtown restoration years ago.

They sit on Metro’s modern metal chairs and slick leather couches, chatting with 10 or more of their peers: clean-cut young men in slacks and dress shirts, or jeans and fitted tees, outfitted from new downtown boutiques like Stitch and BeauMonde.

Across the room, a mural depicts the downtown Sarasota skyline as though it were Chicago or Seattle.

Matt Orr strikes a commanding presence: Tall and boyishly handsome with a quick smile, the 30-year-old Michael Saunders realtor greets everyone—he seems to know every person who crosses his sight—with a hug and a “Hello” in his disarming North Carolina accent. For Orr, who stormed onto the scene four years ago and co-founded Sarasota’s Young Professionals Group, networking comes naturally.

He recognizes an older couple at a nearby table and strikes up a conversation, introduces the pair to Dylonn Cole, a 29-year-old hair stylist from Indiana who can walk to Metro from his Laurel Park home—a live/work space that also houses his own newly opened salon. Cole, too, greets strangers as though they’re familiar friends and talks proudly of his salon’s urban décor, and of convincing his brother to join him in Sarasota. “I love it here,” he explains, “and your mission becomes to get people from up North to join you.” Everyone offers to buy everyone else a drink.

On weeknights, after 10-hour days, these same kids— Michael Saunders realtor next to Creative Loafing journalist next to Phoenix Academy teacher next to Mote Marine scientist—often grab a seat at Metro’s bar, briefcases or laptops in tow, planning to get a little work done, but their gregariousness usually gets the better of them. Even a Tuesday at Metro can stretch to midnight, an aria of young voices accompanied by chardonnay and apple pie a la mode.

On this night, Metro is a jumping-off point, an aperitif. No one is thinking about work. As the evening’s jazz guitarist starts his first set, it’s time for the kids to head out.

“OK,” Orr addresses the whole group, and anyone else who might be listening. “Where are we going?”

The choice is unanimous: Selva Grill.

Downtown Sarasota is like a small liberal arts college. People play sports or put on plays, join frats or log long hours at the library, but at the end of the day, everyone winds up at the same places. Selva Grill is one of those places.

9 p.m. In Selva’s dim red lighting, next to a dining room wall of swirling artwork, girls’ night out is already underway. Marketing maven Nicole Kaney, a 27-year-old native, joins a group of friends—other poised, friendly young women including Meghan Foley (Andrew’s older sister and business partner)—for ceviche and cosmopolitans, comfortably sporting strappy heels and sleeveless dresses, their outfits changing hue under Selva’s bold light show of an interior design. Their conversation pauses occasionally as they greet other parties of four or five young, downtown regulars—among them, SunTrust’s Kyla Yeager, 24, who moved to Sarasota from New York less than two years ago. No one is surprised to see familiar young faces among Selva’s largely older crowd.

Upon arrival, the boys from Metro hit Selva’s narrow lounge behind the bar for martinis and Peruvian appetizers—anticuchos and yucca a la Huancaina. The bartender greets them by name.

Settled into the scene, everyone lingers until after 11. The night is still young.

***

In many ways, this cool downtown crowd—and the professional and social opportunities it enjoys—had its nascence in the ‘80s and ‘90s, when kids like Kaney and the Foleys were school chums growing up together in Sarasota. A web of childhood friendships binds together these prominent young downtowners, who are grabbing attention with their business success and community contributions. Today’s fashionable hair stylist grew up with the Rosemary District’s PR wiz, who went to high school with the State Street boutique owner. Kaney and Meghan Foley met in elementary school. A decade ago, Andrew Foley worked with sought-after gala chair Emily Walsh Parry at the Colony.

Networking is that much easier when downtown’s latest business leader used to sit behind you in homeroom.

Theirs is the generation that tipped the scale for Sarasota young people. When they hit their 20s and looked at their options, those native sons and daughters saw that Sarasota had grown enough jobs—and lured back enough childhood friends—to make returning home worthwhile. And that core of youth drew other young people—ambitious go-getters who forged spots for themselves in established downtown businesses like Michael Saunders, SunTrust or LexJet, or who purchased or created their own businesses: salons, boutiques and bookstores that catered to the growing youth market. The dynamic social scene soon followed.

“I’m constantly amazed when I go out how many young people I’m seeing and meeting downtown,” says Andrew Foley, who returned to his hometown from San Francisco three years ago and was inspired to stay. ”I fell in love with Sarasota all over again. I started meeting great young people from across the country who were committed to being here and making the best of it—and they were having a blast.”

Foley met ambitious out-of-towners like Cole and Orr, who saw in this small city the opportunities to stand out professionally and be heard. They joined arts boards and event committees with Sarasotans twice their age—Sarasota’s culture, after all, is as appealing to this generation as it is to the previous ones—and they created groups like the YPG to gain social and cultural clout. “In a larger urban place, maybe we couldn’t make that difference,” says Orr. “Here there are things to do.”

And Sarasota soon began to reciprocate their enthusiasm. The Van Wezel Contemporaries was created to encourage their input; the Sarasota Film Festival recruits their participation. Across the town, causes compete for their attention.

Living in condos in Courthouse Centre or the old Orange Blossom building, as Yeager and Andrew Foley do, or in homes in Laurel Park or Alta Vista, like Cole and Kirschner, many of these young professionals love traveling no more than five minutes from home to work, from the gym to the grocer, from shopping to nightlife. The key to the downtown lifestyle, says Kaney, is “staying within the zip code.”

Kaney, who made her name as marketing director for downtown Sarasota’s Whole Foods, now works with the Rosemary District’s Wingspan Marketing. She and her husband, a sales manager for LexJet on Fruitville Road, “have a five-minute commute,” she raves. “We walk to lunch—Derek’s and the Sarasota Olive Oil Company. We buy all our groceries at Whole Foods. We have big-city jobs in a small city.”

In fact, most of this crowd shops at Whole Foods. Besieged by youth and flanked by concrete, the store turned something as simple as grocery shopping into an urban experience. "Whole Foods made me feel like I was in the city again," says Yeager.

But arguably the biggest gain for the burgeoning city scene was the recent arrival, at long last, of hip, upscale shopping opportunities. “So many cool, stylish people used to drive all the way up to Tampa, just to buy a shirt to wear out in Sarasota,” says Vinny Sizemore, 35, co-owner of the six-month-old, SoHo-inspired Stitch Boutique on Main Street. Sizemore, too, spent his teen years here, and he, too, was recently drawn back by family and friends—as well as entrepreneurial opportunities. In Manhattan, where Sizemore spent years working in the fashion industry, Stitch would be only one of thousands of upscale T-shirt-and-jeans boutiques; in downtown Sarasota, the chic small space lined with hip denim, rock-star shirts and striking accessories is a sartorial standout, one of only a handful of fashion hot spots.

But it’s a high-quality handful; Tampa is no longer a necessary drive for Sarasota shoppers. Nowadays, style-obsessed downtowners don’t have to travel even as far as St. Armands to find stores, such as Main Street’s Lotus and Stitch and State Street’s BeauMonde, with the fashion standards of Los Angeles or London.

Like everything else, shopping downtown is a social experience. Sizemore greets every customer—many of them familiar faces from high school or nights on the town—honing in on personal style and the Sarasota scene. He warns a downtown partier away from a particular William Rast top; a prominent young gallery owner bought the same one the day before.

You know this crowd has made it when running into someone else wearing the same $100 T-shirt is a legitimate concern.

***

At midnight on Friday—no earlier—various groups begin to migrate from Selva to upper Main Street, congregating under the blue neon sign of Esca, a two-story Italian restaurant where everyone, it seems, winds up at the end of the night. The upstairs bar soon teems with young people—and in this venue, at last, only young people. Orr, Cole, Kaney and the Foleys disappear into the crowd, which spills out in multiple directions through sliding glass doors onto Esca’s terrace, where the lights of downtown Sarasota stretch out before them.

The few high-top tables, inside and out, are already taken, and the floor fills with standing conversations—young men in khakis and Oxfords, art students with pierced lips, couples draped on each other, oblivious to the world. In the center of the room, people gather around a young man strumming a fiery Latin guitar. Behind him on the terrace, girls in colorful halter tops laugh uncontrollably at their own uninhibited dancing, hands behind their heads to hold up their hair, exposing their necks to the cool night air. The music echoes onto Main Street, bouncing off buildings and blending with the sounds of revelry.

Even a few years ago, downtown Sarasota would have been dark and silent at midnight. It couldn’t support this youthful movement yet. The city wasn’t economically dynamic enough to provide their careers, not young or diverse enough to hold their interest. But as growth began to boom, the sophisticated, determined young set committed to downtown; and, paying reverence to Sarasota’s relaxed yet sophisticated personality, they created the kind of city life they wanted—as Orr calls it, “the café lifestyle”—and established a community for the next generation of successful Sarasotans. These are the heirs to the town’s affluent, artistic, entrepreneurial reputation. The scions of Sarasota are coming into their own.