Where To Stay In Winter Park | The Alfond Inn

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.