Back in 1881, wealthy Northerners decided to buy some lakefront land in Central Florida and change the area’s name from Osceola — after the chief of the state’s Seminole Indians — to Winter Park to make it more appealing to vacationers. Little did they know that a century later nearby Orlando would grab the attention of most of those vacationers as the theme-park capital of the world.
Still, downtown Winter Park remains a year-round vacation gem, best enjoyed at a slower pace. Next time you’re in Central Florida take a little detour to Winter Park for a satisfying 48 hours.
4 p.m.: Begin your stay at the Alfond Inn, which is within walking distance of Park Avenue, the city’s upscale shopping street; Central Park, the farmers market and the liberal-arts institution Rollins College. In fact, the luxury boutique hotel, with 112 guest rooms, is owned by the college and displays much of the Alfond Collection of Contemporary Art on its lobby and hallway walls. Opened in 2013, it was built to raise money for scholarships, bolstered by an endowment of the Alfond Scholars Program.
The hotel has several open seating areas, some lined with bookshelves stocked with Rollins’ yearbooks. See if you can find the 1951 yearbook featuring Fred Rogers (aka Mr. Rogers) as a senior (he graduated with a B.A. in music). (1-407-998-8090; thealfondinn.com.)
6 p.m.: Have dinner at Prato, considered one of the city’s best restaurants. It offers hearty, rustic Italian cuisine, served in a cool, hip atmosphere that makes it feel like a “real Manhattan-style joint,” according to reviews on Zagat. It also offers year-round patio dining, facing the expansive Central Park (1-407-262-0050; prato-wp.com.)
7 a.m.: Grab breakfast at the Winter Park Farmers’ Market, now in its 36th year. The road is closed at 200 W. New England Av., in front of the restored historic train depot. Eighty vendors offer local produce, all kinds of plants, baked goods, spices and more. Operates from 7 a.m. to 1 p.m. every Saturday, except the third one in March, when the popular Winter Park Arts Festival takes over downtown.
9:30 a.m.: The centerpiece of the Charles Hosmer Morse Museum of American Art is the world’s most comprehensive collection of artist Louis Comfort Tiffany’s works. In 2011 it opened a 6,000-square-foot wing to exhibit art and architectural objects from his Long Island country estate, Laurelton Hall. Built between 1902 and 1905, Laurelton burned down in 1957, but thankfully many of the objects were rescued. The museum has re-created the mansion’s Daffodil Terrace, installed in a glass-enclosed gallery; its dining room; its living room, and Fountain Court. You’ll also find the brilliantly colored windows, mosaics, marble, jewels, glass, stone and furnishings that make up the chapel interior that Tiffany created for the 1893 World’s Columbian Exposition in Chicago. It was his appearance at this exposition that elevated his work to the international stage. And there’s much, much more.
Don’t pass up the gift shop, which includes a wonderful collection of Tiffany-inspired patterns and glass replicas, books, scarves, jewelry and unusual items (1-407-645-5311; morsemuseum.org.)
Lunch and shopping: The eight blocks of Park Avenue offer classy boutiques, mom-and-pops and high-end chains. Along the strip you’ll see fashionably dressed shoppers, many speaking French or Italian, making an afternoon of it. Elegant and tasty spots are scattered about: Cafe de France, Boca Kitchen Market Bar, Orchid Thai Cuisine, Bistro on Park Avenue, Pannullo’s Italian Restaurant, to name a few. The avenue has long been dog-friendly and many shops and restaurants allow you to bring them along (experienceparkavenue.com).
5 p.m.: For a drink, stop at the Wine Room. The place offers 156 wines for tasting via wine-dispensing machines. They’re equipped with an Italian-made wine-preservation system that delivers a fresh sample every time. The machines allow patrons to choose from 1-oz., 2.5-oz. or 5-oz. pours.
To get started, purchase a wine tasting card ($3). It acts like a debit card and can only be used on the machines. Load whatever amount of money you wish onto the card and the sampling begins. All wines are available for purchase by the bottle. Cheese and other appetizers also are sold (1-407-696-9463).
8 p.m.: Dinner at the family-owned Bosphorous Turkish Cuisine is a must. Bosphorus is the name of the strait that lies in the center of Istanbul and forms part of the continental boundary between Europe and Asia. Chef Halil Ertane prepares a variety of authentic dishes, wowing the crowds with his table-sized lavas or hollow bread. Most of the staff is Turkish (bosphorousrestaurant.com).
8 a.m.: Brunch at the Briarpatch Restaurant is a favorite among locals and visitors alike. Great place for people watching if you can snag an outside table. It’s known for its homemade lemon raspberry pancakes, brioche french toast, truffle fried eggs, prosecco white peach bellinis and cheese grits (thebriarpatchrestaurant.com).
10 a.m.: Spend the morning seeing the town by water or bike. Winter Park is known for its chain of lakes, many graced with beautiful Spanish-style mansions. Since 1938, the Scenic Boat Tours have taken visitors to explore these lakes, which are linked by narrow canals lined by tall cypress trees. Today, the company offers 18-passenger pontoon boats that operate every day from 10 a.m. to 4 p.m., on the hour. You’ll find the boat dock at 312 E. Morse Blvd., at the end of the parking lot across from the First United Methodist Church ($12 adults; 1-407-644-4056).
If you’d rather see the neighborhoods by bike, rent one at Breakaway Bikes. Beyond downtown, seek out Kraft Azalea Gardens on Alabama Drive that also will take you to Via Tuscany, one of the city’s most beautiful red-brick avenues lined with lakefront mansions. The houses just get bigger and bigger as you pedal your way to Via Lugano, over the bridge and onto the little (private) island called Isle of Sicily in the middle of Lake Maitland (1-407-622-BIKE; breakawaybicycleswinterpark.com).
1 p.m.: About a 10-minute walk from the Alfond is the Albin Polasek Museum & Sculpture Gardens, the retirement home of Czech-born sculptor Polasek, who immigrated to the U.S. as a woodcarver in 1901. He moved to Florida in 1949 after 30 years as the head of the Department of Sculpture at the Art Institute of Chicago. In 1961, he and his second wife set up a foundation to share his life’s work with the public. That year he opened the galleries, chapel and gardens at his picturesque estate on the edge of Lake Osceola, and the residence was opened as a museum in 1988. He created 400 works during his lifetime (he died in 1965). Two hundred are on the museum property (polasek.org).
Also on the property is the 1885 Capen-Showalter House, which was moved there in 2013 in a herculean campaign to save it from demolition. It had been built on the other side of Lake Osceola, and through the effort of three preservation groups and a $450,000 fundraising campaign, the 200-ton house was cut in half and floated across the lake to the Polasek museum grounds. It is being restored to serve as museum offices, exhibition space and a venue for special events.
4 p.m.: Off to Disney World.