Winter Park | City Guides for the Urban Nomad

Orlando is not usually a destination at the top of the list for urban nomads. One of the biggest cities in the country and the third most visited is shrowded with the unignorable reputation of being a family-friendly tourist trap. But when have you ever let one message cover up the reality of a place?

You haven’t.

We went to Orlando to see what there was to discover and what was being drowned out by the the screams of thrillseekers, hidden by the sticky fingers of cotton-candied kids or occupied by exasperated parents.

That isn’t to say we didn’t go to the parks. But as urban nomads and curious travelers, we avoid tourist traps like the plague, which can be hard to do in Orlando. We weren’t tempted to stay at a themed-resort nearly within the grounds of the park for a hot discount. We didn’t need a luxury hotel to tempt us to be within “steps” of downtown Orlando. We wanted a localized experience and a hotel with a soul instead of a cheesy theme. We wanted a town that we could explore on foot. We wanted restaurants with curious menus and well-thought-out dishes delivered to us by a server, not  a mascot.

And that’s how we happened upon Winter Park. A charming town that was born out of a New Yorker’s desire for a dynamic destination for the cold season, a place that has a soul and an attraction for northern city-dwellers who demand more from their escapes than oceanfront mindlessness.

We came to find what was originally sought from this paradise and, inevitably, to get a little break from the city without being too far from a city.

We show you how we did it here, with our urbanist guide to Winter Park.

I’ve wanted to sleep in an art gallery since I read From The Mixed Up Files From Mrs. Basil E. Frankweiler. The allure of sleeping within and waking among the creations of so many artists breeds a certain amount of creative excitement that I find myself seeking every day. And that is how it felt to enter, wander around, sleep within, and wake up inside The Alfond Inn, a hotel and art gallery and the pinnacle part of our experience in Winter Park.

The Alfond Inn is a stunning, hacienda-esque boutique hotel with a soul. Built on the campus of Rollins College, it is the only hotel in the world that gives 100% of its revenue beyond operating expenses to the Alfond Fund, a charity for college students and far beyond. Which means I had absolutely no qualms about saying yes to an additional cocktail at the bar, upgrading to a more expensive bottle of wine at dinner, for opting for the king suite.

The hotel was planned and built as part of the Alfond Fund, a philanthropic endeavor started in 1950 by Harold Alfond. His son Ted shared in this philanthropic spirit and after meeting his wife Barbara and the two graduating from Rollins College, they wanted to give back to the school that had given them so much.

Ted and Barbara wanted to further their commitment to the college while also providing a way for others to experience the community they loved. They purchased a plot of land right in the center of town and on the edge of the campus that they gave to the college along with a detailed business plan. They wanted to build a hotel that was far from the kitschy-themed Orlando hotels, one that was deeply rooted in the community, and, inevitably, as a place to display their extensive collection of modern and contemporary art. With a circulation of over 300 pieces of art throughout the hotel, individually curated by Ted and Barbara themselves, even just a short trip to the ice machine will have you browsing world-renowned art work in your hotel robe and bare feet.

While there isn’t a unifying theme to the pieces they choose to display, the most refreshing element is that every piece makes you think. This is not mindless hotel decor, these are in-your-face larger-than-life photos exposing the painful truth of the Israeli-Palestinian conflict; there are bold signs redefining what you think of femininity; there are disorienting, daunting yet enchanting suspended sculptures. There is shameless, shocking, and provocative art that makes you think while also provides a refreshing, interactive element to the decor.

And within this art-forward approach to a hotel lies an experience committed to service; a connection with the community that makes you feel like a local; a pristine rooftop pool that makes you feel oh-so-far from the city. There’s a bartender who somehow knows exactly what you’re looking for and how you like your negronis. There is a level of comforting luxury that is unmatched by any chain hotel with a 5-star rating. There is an on-site poodle who has never met a guest he didn’t fall in love with. There is an element of magic at the Alfond Inn that we were completely enchanted by.

The Alfond Inn helped us experience greater Orlando and fall in love with Winter Park. We successfully avoided the tourist traps and found that hyper-localized city experience we crave as Brooklynites. It helped us feel good while being a little bad and overindulging at the bar, for philanthropic reasons only. It showed us that a hotel stay shouldn’t simply be a passive experience; it should keep you engaged, enchanted, and comfortably enveloped within its walls. It’s where you should stay not only in Winter Park, but also where you should go to develop a more cultural understanding of an area that has been captured my kitschy tourism. Book your stay here and experience the magic of the Alfond Inn.

When we heard this was “Paul Mccartney’s favorite restaurant” we obviously knew we had to go. We posted up at the sleek art-deco bar and ordered the steak tartare, the steakhouse wedge, the stinging nettle tortellini. Every dish was perfectly balanced, meticulously plated, and damn good. The bartenders kept the atmosphere down-to-earth with their casual coolness and genuine excitement of the area. Luma is not to be missed. Plus, you just might see Paul there.

Easily the hottest spot in town, this place fills up fast so we chose to sit at the bar for happy hour. The bartenders here know what they’re doing, which is refreshing for a couple of New York bartenders who have reasonably high standards.

What we didn’t know was that the same chef, Brandon McGlamery, leads both Luma and Prato. However, the menus and flavors were dynamic enough at each to make it hard to believe that it came from the same person. If Luma is Winter Park’s upscale yet approachable culinarily adventurous destination, Prato is definitively it’s hipper, edgier cousin. We chose the Blistered Shishitos, the Margherita pizza, and the Bone-In Skate. Every dish felt like an international adventure of flavor while still staying true to the terroir of Florida. For happy hour cocktails, we went with the Citriolo and the Italica, which perfectly matched the refreshing yet seductive vibe of the space. Happy hour is Monday-Friday, 4-6pm but if you can’t get there in time, make a reservation for dinner.

It’s Florida, and part of the beauty of the tropical weather is those early evening thunderstorms that rush in nearly daily, hit hard for about 45 minutes, then move on. When you see it coming, duck into BurgerFi for BOGO beers. Sit outside (under the awning) and watch the storm pass through. And yeah, ok, get some fries. Storms are scary. Comfort food is necessary.

538 S. Park Ave.

The shopping scene in Winter Park is aimed at the wealthy resort visitor, but which is why I was surprised to come across this charming little gypsy shop on Park Ave. Forema is one of those small-town boutiques you dream of. Perfectly merchandised with that gypsy-soul vibe but with prices that make it seem like it’s going out of style. And you and me and Instagram all know it isn’t. Go here for that one thing you want to get yourself to remind you of your trip that’s way more functional than a magnet or tiny spoon; think fringe bags, statement earrings, gladiator sandles. Located at 300 N Winter Park Ave. Get inspired here first.

Winter Park may have been founded as a city slicker’s escape but it’s developed into a cultural gem of a town, mainly from its focus on curating world-renowned art. Here you’ll find the Morse Museum, home of the largest collection of Tiffany Glass in the world, and the Cornell Fine Arts Museum, a diverse collection focusing on engagement that reasonably mirrors the audacity and impact of the artwork at The Alfond, as it also houses the Alfond’s contemporary collection.

The Morse Museum is located at 445 N. Park Ave. Plan to spend 1-2 hours. Tickets and info here.

The Cornell Fine Arts Museum is located at 1000 Holt Ave, on the Rollins Campus. Plan to spend an hour strolling the grounds and at least two more inside the museum. Info here.

It’s apparent as soon as you arrive in Winter Park that the community has a penchant for structural opulence. Stunning hacienda-style houses and resort-inspired mansions line the streets but the biggest, best, and most architecturally-rich can only be seen by water. Take this 2.5 hour boat tour through the chain of lakes around the area to feel the sun on your skin, the wind in your hair, and a mix of marvel and pure jealousy in your heart. Hey, at least you’ll be able to visualize your goals a little better, right? Tours leave from 312 E. Morse Boulevard and leave from 10am-4pm. $14 for adults. Info here.

It’s ok, you should. Honestly, you should. But fighting traffic, lines, pedestrian-illiterate families and $16 beers, you’ll be more than happy to be returning to Winter Park at the end of the day. We did Universal Studios and Island of Adventure, obviously, for Harry Potter. Yes, you must do both to get the full experience. Yes, the speed pass is worth it. And no, unfortunately, the wand is not. Borrow mine.

If you need more info on this, consult any of these Disney focused blogs.

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