Once the winter playground for the rich and famous, Winter Park is now relegated to being a sleepy suburb of Orlando. It really is much more, however, and deserves consideration for a weekend getaway. You probably don’t need to spend a long weekend here, two days is enough unless you are branching out into other nearby attractions (we recommend Wekiwa Springs State Park if you are). Be forewarned, this is not anywhere near the Orlando theme parks so if your plans include a day or two at Disney or Universal, plan to change hotels or get up early and drive another 30-45 minutes (if traffic cooperates, which almost never does in Orlando).
If you want an authentic Winter Park experience, you have to stay at the Park Plaza Hotel. The hotel has provided rooms to visitors of the town for 100 years. Guests do not come here for five star opulence. Rather, they are looking for character, gilded-age charm, convenient access to the town, and maybe even a few ghost stories. Of course, with a building that old, you would expect it to be haunted and the front desk agent will be the first to corroborate this. The hotel does not disappoint with regards to the former list either. A wrought-iron balcony affords a relaxing view of the shops below, and the rest of the town’s boutiques and cafes are just a short walk from the hotel’s front door. Walking through the front doors you are immediately struck by all the dark wood and ornate carvings. The place exudes character.
Most of what you will want to explore is easily reached on foot. The Central Park in the middle of the downtown/historic district is the site of a Saturday morning farmers market as well as serving as the hub from which the rest of the town’s sites radiate. Smack dab in the middle of the park is an old rail station and Amtrak will still bring visitors here if you prefer to not drive. Around the park you will find enough boutiques to shop until you literally drop (including a few kid-friendly stores), preferably at one of the many watering holes dispersed along the same streets, some of which even feature live music in the afternoons for added ambiance. We had no problem bellying to an outdoor high-top with our daughter to relax with a cold one and listen to music.
If museums are your thing, there a few worth checking out in Winter Park starting with the Charles Hosmer Morse Museum of American Art. This museum houses the world’s most comprehensive collection of works by Louis Comfort Tiffany (yes, that Tiffany). Also worth visiting is the Winter Park Historical Museum. On the day we visited it featured an exhibit on the history of hotels in the region that was really interesting – though as a travel advisor I may be biased. Even our daughter enjoyed the exhibits at both museums, particularly the interactive one designed for kids to get a more hands-on experience. All said and done, there are about a dozen museums in Winter Park of varying sizes and themes.
OUT AND ABOUT
If you want to venture beyond the historic Central Park area of town, you will find some uniquely Floridian opportunities to get up close and personal with nature. Scenic Boat Tours has been offering visitors cruises of three of the seven lakes in the Winter Park Chain of Lakes since 1938. The chance to see wildlife is all but certain and you will get a view of the flora around town that most will never know existed. If you are willing to venture even further, consider making the 20-minute drive to neighboring Apopka, home of Wekiwa Springs State Park. This park offers great opportunities for swimming in the fresh (i.e. cold) spring water or try your hand at paddling the spring run (rentals available). If you prefer dryer pursuits, there are plenty of trails to explore on foot as well. We opted to spend a day here with our 7 year old and she loved it. It took her a minute to build up the courage to jump in the water but once she did, she never wanted to come out. She also loved chasing butterflies through the woods on the trail closest to the spring.