Winter Park: Orlando’s Chic Cousin

by Susan Young
Last updated: 4:00 AM ET, Thu March 31, 2016

Vintage postcard photo via Wikimedia Commons

It may not be L.A.'s Rodeo Drive or Palm Beach's Worth Avenue, but Park Avenue, in the Orlando suburb of Winter Park, packs a punch when it comes to a chic shopping and dining experience.

The one-mile stretch - with Rollins College to the south and the Charles Hosmer Morse Museum of American Art to the north - is jam-packed with boutiques, cafes, a huge park and a train station in between. You'll find small, independent shops alongside large retailers with a mix of funky and fun.

My personal history with Park Avenue goes back to the late '50s when my parents moved us to Central Florida. We settled on the outskirts of Winter Park and I attended the Catholic school on the north end of the Avenue, allowing me to rub elbows with both the rich families who lived in the city limits, and those, like us, whose families couldn't afford the lakeside mansions.

Occasionally I would walk home with a friend whose father owned the Seminole Hotel, on Lake Osceola. We would be welcomed into the kitchen for refreshment and treated like princesses. Other times we would amble to the local Rexall Drugs for a vanilla coke or milkshake then window shop the chic storefronts like Home & Hobby House with its Lalique Crystal dining table adorning the window, or pop into Cottrell's 5&10 for penny candy.

The Seminole Hotel is long gone and the stores have been replaced by more trendy shops, some independent and some chains, but the ambiance of the Avenue remains and is vibrant throughout the year. In that one-mile stretch you will find over 40 restaurants, cafes and bakeries featuring French, Turkish, Thai and Italian along with a myriad of other cuisines.

Accommodations, within walking distance, include the boutique Park Plaza Hotel, built in 1922, located around the corner from the train station; or the new Alfond Inn, just a block from the main drag. The Alfond is located on the site of the former Langford Inn, which housed political guests like Mamie Eisenhower and Eleanor Roosevelt, as well as the Reagans, who stayed for their 25th wedding anniversary.

During the Langford's heyday one might run into Henny Youngman or Hugh Hefner in the Empire Room. Of course, celebrities still visit Park Avenue with recent sightings ranging from Paul McCartney to Carrot Top, a permanent resident. You just never know who might be visiting this cosmopolitan town.

You will find stores such as Williams & Sonoma, Restoration Hardware and Pottery Barn, the latter taking up space in the former movie house, The Colony. Pottery Barn kept the original sign, which is a reminder of time spent on a Saturday afternoon watching movies like "Ben Hur" or "Psycho."

A few of the original stores remain like Simmons Jewelers, Taylors Pharmacy and, the aforementioned, Park Plaza Hotel. And there are a good number of independent shops such as Tuni, Writer's Block Bookstore and the delightful children's shop, "tugboat & the bird." If you're finding the prices a bit out of your range, check out Cida's Consignment Shop on the north end of Park Avenue, where you can purchase Chico's, Chanel and Jimmy Choo at a fraction of the original cost.

Need a haircut? On the south side, Gary Lambert Salon will keep you in style. Gary has been a staple in this town, getting his start on the other end of the Avenue, many decades ago, making us beautiful for proms, weddings and other special occasions over the years. He's a Winter Park treasure.

If you tire of shopping, take a break with the Winter Park Scenic Boat Tour just a block east on Morse Boulevard. You'll be whisked away on a pontoon boat across the chain of lakes, through narrow canals, bordered by those millionaire's mansions. Weather permitting, tours leave every hour from 10 a.m. to 4 p.m., every day of the week except Christmas. Since 1938, visitors have been enjoying this leisurely cruise as an alternative to the hectic tourist areas where the flora and fauna might not be so real.

Another respite from the maddening crowds is the Morse Museum, on the north end, which houses the world's largest collection of Louis Comfort Tiffany. You'll see beautiful Tiffany art glass, lamps, furniture and jewelry, along with the iconic leaded glass windows which have been on display all over the world. In 1893 Tiffany created a chapel for the World's Columbian Exposition in Chicago, which now sits in the Laurelton Hall wing of the museum.

Spending a day on Park Avenue won't disappoint. Exploring the shopping alcoves, sipping a cup of coffee at a cafe, grabbing a bite or just people watching from your perch in Central Park … it's a great reprieve from the crowds and a step back in time where the pace is slow and the style is elegant.

If you can't find a parking spot along the Avenue, there are several free garages from which to choose. Or hop on the SunRail and be delivered right in the middle of action at Central Park. Just make sure you check the schedule, as the train does not operate on weekends or late evenings.

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