Each time I leave my car with the valet at the elegant Alfond Innon the edge of downtown Winter Park, Fla., it is with the excited anticipation of meeting someone special in my life inside.

There was the time I met my husband for an anniversary lunch at Hamilton’s Kitchen, which was sunlit and flower-filled as we dined on fish tacos but received filet mignon service. Or a happy hour in Hamilton’s Lounge to catch up with a former colleague; our young daughters shared a plate of french fries while we sipped martinis in a cozy alcove dominated with bold, modern art. And there was that steamy September evening spent with two old friends, three chef’s specials and two bottles of a crisp sauvignon blanc as we dined al fresco under the portico overlooking the manicured garden courtyard and made a promise not to let so much time pass until we’d meet again.

Spanish architecture melds with contemporary art in the Alfond Inn's lobby.

So when an invite came my way to celebrate the Alfond’s fifth anniversary with a tasting of new dishes from chef Stephen Doyle’s dinner menu and a tour of the most recent installation throughout the hotel from the Alfond Collection of Contemporary Art, I immediately checked my calendar and committed. The Alfond has been part of many touchstone memories for me, and I wanted to be a part of its special moment, too.

When the Alfond Inn opened five years ago, it was as though the final, sorely missed puzzle piece had been placed into the city of Winter Park, located about five miles north of downtown Orlando. The 112-room boutique property echoes the Spanish-Mediterranean revival style of neighboring Rollins College, established in 1885, and many nearby homes that were built in the early 20th century. The Alfond Inn feels, and looks, as though it has always been a part of the Winter Park landscape.

There are two things that distinguish the Alfond Inn from other properties. First, the property is owned by Rollins College, and all net operating income from the inn is directed to the Alfond Scholars program fund, the College’s premier scholarship fund. The goal is to reach a $50 million endowment.

Second is the art. Its public spaces display a portion of the Alfond’s ever-growing collection that currently comprises 400 works and is part of the Cornell Fine Arts Museum collection at Rollins College.

Kicking off this little birthday party, Cornell director Ena Heller said that she and Alfond general manager Jesse Martinez have an ongoing joke. “He thinks he has a hotel with art,” said Heller, “and I think he has a museum with rooms.” Either way, the Alfond works.

“The Alfond Inn is the only art hotel where the collection of a teaching museum is displayed 24/7 for all to see,” Heller added. In other words, “It provides an introduction to art without realizing you are being indoctrinated,” she said.

Truth be told, the menu tasting turned into what felt like a five-course meal: Doyle’s food was so good, I couldn’t limit myself to just a bite or two of each dish. Afterward, we headed out for a tour of the newly installed collection with Cornell curator Gisela Carbonell. “Once a year we change the display very significantly. You’ll see lots of old friends but plenty of new faces.”

I’m always in awe of the art I see at the Alfond. But this time I really noticed how the works speak of our times. For instance, hung in Hamilton’s Lounge, the incredibly comfortable lobby bar, I note a work by Gardar Einarsson called Equality Forever. It is a play on the U.S. Postal Service’s Forever stamps, but in Einarsson’s work, Forever is crossed out and the word Justice is written above it. Another work by Jenny Holzer is of horizontal, colored bars painted in oil on linen. It is a representation of a U.S. government document redacted to the point that there is nothing to see.

This is no accident, said Carbonell, who shares a bit about how each year’s installation is selected. “The art unifies the space but also provides opportunities to have conversations and dialogues about issues that are important to most people,” she said. “So not only art that is beautiful but art that addresses a multiplicity of issues that reflects a liberal arts education at Rollins.”

Hotel guests can immerse themselves in the art 24/7. But nonguests are welcome to explore it, too. Simply come for a drink or a bite to eat and read about the works on the plaques beside each piece. A free public art tour is given every Sunday at 1 p.m., and a happy hour tour is given on the first Wednesday of every month. Can’t make it? Ask for the audio-guide at the front desk or explore much of the collection online.

The 112-room inn is situated in the heart of Winter Park and is within comfortable walking distance of Rollins College and buzzy Park Avenue, which is loaded with shops and restaurants. A favorite outing for visitors is the Scenic Boat Tour that operates daily on the chain of lakes upon which Winter Park was founded in the late 1800s. This is such a walkable area that your clients really don’t need a car if they prefer to rely on Uber for airport transportation.