Back in 1881, wealthy Northerners decided to buy some lakefront land here and change the area’s name from Osceola — after the chief of the state’s Seminole Indians — to Winter Park to make the area more appealing to vacationers. Little would 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. The shaded, downtown brick streets of this bedroom community on Orlando’s northern border touts a museum with the world’s most comprehensive collection of Louis Comfort Tiffany’s works and installations. The state’s first private liberal arts college, Rollins College, is here too.
So next time you’re in Central Florida take a little detour to Winter Park for a satisfying 48 hours:
Downtown Winter Park remains a year-round vacation gem, best enjoyed at a slower pace.
Never miss a local story.
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 Rollins. 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 walls and hallways. Opened in 2013, it was built to raise money for scholarships, bolstered by an endowment of the Alfond Scholars Program. 300 E. New England Ave., Winter Park; 407-998-8090. www.thealfondinn.com.
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 on Park Avenue. 124 N. Park Ave.; 407-262-0050. www.prato-wp.com.
The next day, grab breakfast at the Winter Park Farmers’ Market, now in its 36th year. The road is closed at 200 W. New England Ave., 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.
Then walk over to the Charles Hosmer Morse Museum of American Art. The museum’s centerpiece is 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 1902-05, it burned down in 1957, but, thankfully, many of the objects were rescued.
The Morse Museum has recreated the Daffodil Terrace from Louis Comfort Tiffany’s Long Island country estate, Laurelton Hall, and put it on display here in a glass-enclosed gallery.
The museum has re-created the mansion’s Daffodil Terrace — installed in a glass-enclosed gallery; its dining room; 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. 445 N. Park Ave.; 407-645-5311. www.morsemuseum.org.
Then walk down Park Avenue, an eight-block stretch that offers classy boutiques, mom and pops and high-end chains. There are a collection of elegant and tasty spots 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. http://experienceparkavenue.com/.
For a late-afternoon drink, stop at The Wine Room, which 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. All machines allow patrons to choose from 1-ounce, 2.5-ounce or 5-ounce pour sizes. 270 S. Park Ave.; 407-696-9463.
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. 108 S. Park Ave.; 407-644-8609. www.bosphorousrestaurant.com.
Start your next day with breakfast or brunch at the Briarpatch Restaurant, a 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, bellinis and cheese grits. Open every day, 7 a.m. to 5 p.m. Monday through Saturday; 8 a.m. to 5 p.m. Sunday. 252 N. Park Ave.; 407-628-8651. www.thebriarpatchrestaurant.com.
Spend the rest of 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.
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 between 10 a.m. to 4 p.m. (leaving every hour 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. Adults, $12; children 2-11, $6. Cash or check only. 407-644-4056.
If you’d rather see the neighborhoods by bike, rent them at Breakaway Bikes, 141 Lincoln Ave., off of Park Avenue. Beyond the 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. Breakaway hours: 10 a.m. – 6 p.m., Tuesday-Saturday; 11 a.m. – 5 p.m., Sunday. 407-622-BIKE. www.breakawaybicycleswinterpark.com.
Then check out the Albin Polasek Museum & Sculpture Gardens. About a 10-minute walk from The Alfond is the retirement home of Czech-born sculptor Albin 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 to visitors the galleries, chapel and gardens at his picturesque estate on 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. Hours: 10 a.m.-4 p.m. Tuesday through Saturday; 1 to 4 p.m. Sunday. 633 Osceola Ave. http://polasek.org.