Winter Park, Florida, in Orlando, is the newest bright spot in the Sunshine State

It’s time to let your prejudice go. Florida is, well, it is everything you think it is, but it’s also a whole lot more than that. Winter Park is solid proof. A little touch of New England, in Orlando, Florida.


So yes, Miami is bam-booming, Jacksonville is the new artist hub thanks to Art Republic and an engaged mayor, and the beaches on the east side of the revolver state will always be sunny and purple-rise smiley. Orlando remains one of the biggest attractions in the world thanks to Universal Studios plus it’s marvelous rival Disney. It’s not called the “happiest place on earth” for nothing. Eye rolling at Florida, whilst enjoying the climate, is typical, and pretty much uniquely, New Yorker behavior. But save that face for another destination.



Winter Park, Florida 2
No egrets about coming to Winter Park…Hahahaha! Daniel Scheffler



Because away from the crazy theme parks, scary opinions and the maddening crowds, is this little area in real Orlando called “City of Homes” or Winter Park. And your people (yes, yours too) are here. Tilda Swinton once said that “Orlando” is a biography of her life — of course, the erudite actor was speaking about Virginia Woolf’s book Orlando, published almost a century ago. Now take your thoughts of Orlando, Florida, and transpose it with this epic book’s themes, virtue and alluring thoughts. Even some of the beauty might do your mind well. And let’s see what we have now:


Winter Park, Florida 3
Woof Daniel Scheffler

Sunsets were redder and more intense, dawns were whiter and more auroral. Of our crepuscular half-light they knew nothing. The rain fell vehemently, or not at all. –Virginia Woolf, Orlando.


Aptly so, Winter Park was plotted in 1881 (then called Lakeview) by wealthy northeasterners escaping the harsh winters of Boston and those surrounds. And for the next sixty years or so it very slowly remained just that, a quiet sweet-spot in the middle of Orlando hidden in plain sight. With very few residents too, a handful in 2000 that has grown to less than 30,000 this year. But in 1945 the architect James Gamble Rogers II was hired to design a retail component (with a mindful attachment to aesthetic) to this joint — setting off even more European vibes. Note no big box stores, bad chains and scary strip mall heinousness here.


Think of casually strolling along your favorite European town — in Spain or Portugal — and think of the smell of fruit trees, the big colors of endemic flowers and the joy of living the locals just emanate. Well, Winter Park, with its blooming red hibiscus and wholesome energy, rivals that. Some locals say that the scent of the famed citrus of the area wafts through these leafy streets, when the warm air blows a certain direction.


Today it is home to Rollins College, a private liberal arts college founded in 1885, attracting the right kind of cognoscenti from all over the world. And so a town within a city, loved for its subtropical paradise loveliness, is where art, education and soft Spanish moss congregate. And the best thing? The old money here doesn’t flash, but mingles furiously.



Winter Park, Florida 4
House on Lake Maitland Daniel Scheffler



This little smart enclave (enter words like diverse and inclusive here if you will) in the middle of Florida feels like a sip of Europe, with sidewalk street cafes and fecund trees and shrubbery, all close to these oversized bodies of water. The most frequented, Lake Virginia, gives the allure of full-blown nature living in the middle of the city — a sort of aquatic Central Park. Complete with teeming bird life, and kitsch little boat rides to stretch the legs. Fitbit that please.



Winter Park, Florida 5
A scenic boat tour on the Winter Park chain of lakes Daniel Scheffler



Winter Park, Florida 7
Where the grass meets the water. Meet us in Winter Park Daniel Scheffler



But it is this Park Avenue, Winter Park’s main street, that is the city’s life fount. Walk it, don’t drive it or bike it, locals will remind you wherever you go. The sweet brick streets, locally-owned stores, the many tree canopies and all this greenery offers a new kind of downtown city life. A city focused on preservation, peacefulness and lifestyle and not growth, now has the perfect continuation of their original outset more than a century ago.


Who knew that somewhere Florida would arise with a gentle reminder of a slower, more meaningful and conscious life?



Back in the day… The Hotel Alabama, circa 1950s, was the place to stay, and was one of the first developed properties in Winter Park, fifty years before it became a hotel Photo provided by Wonderlust





Owned by Rollins College and opened in 2013, The Alfond Inn is right where you want to be to cruise around town.


If you’re looking for the best hotel in the entire greater area with all the amenities and plenty of gorgeous space, it’s naturally the Four Seasons Orlando. Although it’s further from Winter Park (about 30 minutes south) it’s worth it if you want the full monty: spa, golf, a big pool, suites and kid-friendly facilities.





The food in Orlando can be rather scary, but Prato (in Winter Park) has been the game changer in this city. Perfect Italian for any occasion, or non-occasion.


If you want new American cuisine with an extensive wine collection, Luma on Park delivers.


Coffee your thing? Foxtail Coffee, close to Park Avenue, sources well and even offers coffee courses.





Pick up some old school notebooks at Rifle Paper Co.’s flagship.


John Craig is ideal for all your waspy menswear needs.