Winter Park is a good day trip from anywhere on the west-central coast of Florida, but it's a better overnight trip. You could even stretch it to a full weekend. Though it has no beach or megaresort, this little city north of Orlando, tucked around a necklace of lakes, has plenty to do and almost all of it is within walking distance if you begin at its center. Winter Park's heart is a compact downtown with both small-town charm and cosmopolitan sophistication.
Park Avenue is the main drag, a two-lane brick ribbon that's more pedestrian- than car-friendly, its broad sidewalks dotted with lush planters and sidewalk cafes. It runs north out of the downtown, but the official shopping district is about eight blocks long. Each end is anchored by a major attraction, the Charles Hosmer Morse American Museum of Art, with the most comprehensive collection of work by Louis Comfort Tiffany in the world, and Rollins College, a top-ranked institution that has one of the prettiest campuses in the state.
The drive to Winter Park on Interstate 4 can be — let's face it — stressful. From my base in St. Petersburg, it takes about 21/2 hours, a lot of that time spent avoiding big trucks and obsessed commuters. You pass all the exits that lead to the great maw of theme parks and major tourist destinations, continue through the Orlando overpasses that can slow to a crawl, and turn off at Exit 87 on to Fairbanks Avenue.
It's a commercial road. Mind the 35 mph speed limit. Several cars, still in highway mode, were pulled over for speeding when I traversed it. After about 2 miles, take a left on to S Park Avenue and you're in another world, old Winter Park.
The town was founded in the early 1880s the way most Florida towns were, by wealthy Northerners looking for a respite from cold winters. The area was platted for residential and commercial buildings with strict architectural guidelines, and a railroad spur was established. During the land bubble in the mid 1880s, land values rose from $2 per acre to more than $200. In 1885, Rollins College was founded by the state as Florida's first four-year college. A large resort sprung up on one of the lakes, private mansions were built and orange groves flourished. Orlando was founded about the same time but grew faster and exploded in the early 1970s when Walt Disney World opened.
Like the rest of the state, Winter Park has seen boom-and-bust cycles but for decades has flourished as the anti-Orlando, purposely resisting office and condominium towers — limiting heights to about four stories in the historic center — and cultivating a reputation for the arts. The Winter Park Sidewalk Art Festival, for example, is one of the biggest in the state, attracting more than 350,000 visitors during its three-day run. This year's festival is Friday through Sunday.
Winter Park has only two hotels, the Park Plaza Hotel and Best Western Mount Vernon Inn. The latter is a bit away from downtown; the Park Plaza, on Park Avenue, puts you at the epicenter. It was built in 1922 and retains many original features. That can be good and bad: the bathroom was small and walls were thin. We heard every word of our neighbor's telephone conversations. But the bathroom was well stocked with upper-end toiletries, comfy bathrobes are provided, mattresses and sheets are great and a complimentary breakfast of coffee, juice and muffins is delivered at your beck and call. Its 28 rooms are on the second floor, accessed by a vintage elevator in the small, antique-filled lobby on the ground level. Some rooms open onto a balcony spanning the upper level; the wrought iron railing and pots of hanging ferns overlooking the avenue will remind you of New Orleans. But this isn't a place for boozy night crawls like those of the Big Easy. Winter Park is a quieter easy. (Word of advice: Some guests complain that the rooms not facing Park Avenue are noisy from the train hurtling nearby in the wee hours.)
To get a sense of the topography that enchanted the town's early settlers, take the Scenic Boat Tour. It has been running since 1938 and leaves every hour on the hour from 10 a.m. to 4 p.m. from a small dock two blocks off Park Avenue. The hourlong ride on a pontoon takes you around three of Winter Park's six lakes and its network of narrow canals built to connect them in the days when a small logging industry was operating. Our skipper was Capt. Dan, whose narration included jokes obviously retold thousands of times and canned repartee, but he provided lots of information about the glamorous houses lining the water and was a wealth of information when asked questions.
Land side, you can spend the better part of a day (or two) visiting museums or going in and out of shops (about 120) along Park Avenue and its cross streets.
The Morse Museum has become an arts destination since its Laurelton Hall Gallery opened in February, a new wing celebrating Tiffany's ultimate aesthetic achievement, the Long Island home on 600 acres he designed and furnished and which was destroyed by a fire in 1957. Rollins has the Cornell Fine Arts Museum, with a solid collection of European and American paintings, sculpture and decorative arts.
If retail is your preference, you will be gratified by the absence of that mall feeling. Though there are a number of high-end chains like Williams-Sonoma, Pottery Barn and Restoration Hardware, the independents are more fun and surprisingly strong with three times more of them than franchises. You can rest your feet on a bench in Central Park, which stretches along four blocks of the avenue. The track bisects it, and a train roars through several times a day. The Amtrak passenger train stops daily at the little station. If you're up for a spontaneous adventure, board it for a run south to Miami or north to New York.
Eating poses a problem: There are so many choices. The downtown shopping district offers dozens of restaurants, sandwich and coffee shops, and chocolate, pastry and candy purveyors. One of the oldest and most beloved is the Briarpatch, generally packed at peak hours. The servings are enormous. My friend and I shared breakfast orders of Brie- and raspberry-stuffed French toast and the Southern platter of eggs, cheese grits, bacon and fabulous fried green tomatoes.
Dinner was at Luma on Park, across the street from the hotel. It was sumptuous in a different way. The chef follows the popular trend of sourcing local ingredients whenever possible and creates innovative combinations on the plate. Not especially hungry, we nevertheless slurped down kale-stuffed ravioli in a broth infused with prosciutto, "local speared flounder" on a bed of black chickpeas (a first for me) and a lovely braised beef short rib. And forced ourselves, for reporting purposes, to try a Meyer lemon tart and slice of hazelnut olive oil cake. Both with strawberry ice cream. In the (translated) words of Edith Piaf, I regret nothing.
The only time we got in the car was for a drive several miles to the Ravenous Pig for lunch. I had to try it; chef James Petrakis was recently nominated for Best Chef-South by the James Beard Foundation, and it's one of the most popular eateries in the Orlando area. And, yes, we pigged out, although there was less pork on the menu than I would have expected. We loved everything — soft pretzels with a Taleggio fondue, house-made charcuterie (especially the chicken liver pate) and the smoked pork sandwich — but swooned over the cauliflower soup and fought bitterly over bacon hush puppies that bobbed in the bowl with the soup.
We packed a full agenda into our overnight visit and wished we could have stayed one more to see things we hadn't time for: the Cornell Fine Arts Museum, Kraft Azalea Park and Hannibal Square (another historic area), to name a few. We never were tempted to stray into Orlando.
My friend, who is well traveled, made an insightful comment as we left Park Avenue and Winter Park, headed for home.
"We always think we have to get on a plane or go far away to find something different and new," she said. "But then we discover that it's right here."
Lennie Bennett can be reached at firstname.lastname@example.org or (727) 893-8293.