We are firm advocates for seeing something of the “real” Orlando when you visit this part of Florida, and there is one place that ticks all the boxes for a genuine experience in the authentic nature of this huge metro area.
It’s a city suburb called Winter Park, a well-to-do and upscale neighbourhood that started out as a winter haven for wealthy socialites from the New York and Boston areas in the 19th century and is now a picture-perfect area of sophisticated charm and attractions.
Founded in 1881, it lured the rich and famous with its stately trees, parks, brick-lined streets, spectacular homes, museums and picturesque lakes, plus the fine shops and restaurants along its main thoroughfare, Park Avenue. In short, it is a picture-postcard destination packed with a café society feel that is more reminiscent of Europe than the USA, and is well worth exploring for a memorable day out.
It is just five miles north of downtown Orlando, 22 from Walt Disney World, and easy to find off main motorway I-4 (junction 87, Fairbanks Avenue). Yet few visitors discover it, and we think that is a real shame, because it is such a wonderful change of pace and style from the theme parks, a place where you can really slow down and admire the elegance and beauty.
Winter Park is also the home to the oldest university in Florida, the 1885-founded Rollins College, as well as a unique nine-hole golf course that opened in 1914, and the largest collection of art by Louis Comfort Tiffany (of Tiffany’s jewellers). The classic, 22-room, 1922-built Park Plaza Hotel can also be found here, which boasts a fascinating view of Park Avenue in the 1920s as shown by a huge vintage photograph on its main staircase.
So, if this really piques your curiosity (as it should!), here’s how to have a great day out and not have to dig too deep into your wallet.
Start by heading to E. Morse Avenue, where you’ll find the long-running Scenic Boat Tour. Established in 1938 and running from 10am-4pm daily, this one-hour jaunt on the three main lakes and canals of the Winter Park area is a glorious journey into the history, wildlife and topography of the city, providing great views of the lakefront mansions as well as Rollins College itself. It costs $20/person ($10 for children under 12) on one of their 18-passenger pontoon boats, and all tours are on a first come, first served basis.
Once you have completed your outdoor tour, head indoors at the superb Charles Hosmer Morse Museum of American Art, which includes that fabulous collection of Tiffany artwork. This classy building is packed with interesting jewellery, pottery, paintings and art glass from the 19th and early 20th centuries, as well as the headline exhibits, which are Tiffany’s stunning Chapel for the 1893 World Expo in Chicago and the partial recreation of his astounding Long Island country estate, Laurelton Hall, which tragically burned down in 1957. The gift shop alone is a real treasure, but you can easily spend two to three hours exploring all the many artworks.
After all that art and culture, you’ll want a nice meal break, and Park Avenue is the perfect spot for great pavement dining and people watching. There are several dozen excellent restaurant choices set out along the pavement on one side of the street, facing Central Park, and you simply can’t go wrong at any of them, which range from great Turkish, Thai and Mexican options to Michelin-recommended venues such as Ava Mediterraegean and Omo by Jont. Barnie’s is an excellent spot for coffee and a light lunch, as is George’s Café and the New General Café & Coffee Bar. From recent trips, we can definitely recommend each of Luca Turci (for fabulous Italian cuisine), the new American style of Boca, the locals’ favourite of The Briarpatch and the Italian gastropub vibe of Prato.
Shopping is Park Avenue’s other key feature, and you can easily spend an hour or two in the afternoon checking out the original stores, galleries and boutiques mixed in with all the restaurants. One-off delights include the Spice & Tea Exchange, Haven Uncommon Goods, Antiques on the Avenue, The Ancient Olive and the children’s store, Tugboat and the Bird, as well as no fewer than seven jewellers. You’ll also want to check out the awesome hand-made sweet treats and ice creams of Peterbrooke Chocolatier!
Keep going to the south end of Park Avenue and you’ll find the lovely campus of Rollins College, where there is a superb memorial to famous alumnus Fred Rogers, who created the much-loved TV character Mr Rogers. A Beautiful Day for a Neighbor is a wonderful sculpture tribute to Rogers, and is open to all visitors to the campus. The Rollins Museum of Art is another artistic Winter Park gem and offers free entry six days of the week (closed Mondays).
Finally, if you’ve really got the Winter Park bug, you might want to consider an overnight stay, in which case The Alfond Inn is a truly gorgeous boutique hotel run by the College, with an excellent restaurant and elevated pool area that is quite sublime. Even if you don’t stay here, it’s worth a look, while dinner at Hamilton’s Kitchen is a real treat for a special night out, especially in the eye-catching patio courtyard. Its Central Florida-inspired menu is fuelled by fresh local ingredients, and it would definitely make our Top 10 of Orlando’s best restaurants.
For more Winter Park highlights, there is the weekly Saturday Farmers Market, Kraft Azalea Garden, historic Casa Feliz and Albin Polasek Museum & Sculpture Garden. Yes, it really offers a packed day out (and a bit more besides!). You can look up more about it here: https://cityofwinterpark.org/.
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