On a lovely Sunday morning, I strolled through the enchanting Kraft Azalea Garden in Winter Park. My heart swelled with joy after every stride, soaking up views of Lake Maitland while meandering along picture-perfect manicured lawns dotted with cypress trees dripping with Spanish Moss.
As I stood in awe, admiring the Exedra, an ancient Roman-style curved pavilion, an unfamiliar voice drifted into the moment. “Isn’t it gorgeous?” I turned and locked eyes with the stranger and agreed that the gazebo overlooking the serene lake is one of the most beautiful scenes in Central Florida. With a crisp breeze whispering through the air and the sound of nesting egrets in the distance, this dreamy stroll reminded me why I adore the charming town of Winter Park, Florida.
Welcome to Winter Park, a gorgeous lakeside community five miles north of downtown Orlando. This city of 30,000 residents is known as the “premier urban village in the Sunshine State” for its cultural diversity, immense natural beauty, walkable downtown, and old-world charm.
A leisurely walk along Park Avenue, the cobblestone, tree-lined “Main Street,” transports you to a small European village with timeless elegance. The town is brimming with upscale boutiques, delightful cafes and bistros, museums, and breathtaking natural landscapes. On weekends, you’ll be greeted with a vibrant brunch crowd, locals walking their dogs, tourists perusing the corridors to explore the many shops, and families spending quality time inside Central Park.
Not far from the bustling downtown district is a series of six lakes—the Chain of Lakes—connected by a network of Venetian-style canals. The scenic waterways are a wonderland for paddlers and a portal for daily boat tours that take guests on a sightseeing journey to learn the history of this gorgeous urban oasis.
History awaits around every turn as you wander through neighborhoods with European-style homes donned with century-old oak trees and lush, manicured gardens. Moreover, museums, antique shops, and art galleries are plentiful here, and the historical landmarks and gorgeous architecture will entice the history lover in you. What’s more, Winter Park is home to the iconic Rollins College, the oldest private college in Florida. The lakeside campus with brick walkways, picturesque courtyards, Mediterranean Revival buildings, and historic charm is an extension of the Old World community.
With all the sights and sounds of Winter Park, there is something for everyone to love about this hidden gem village near Orlando.
True to its name, Winter Park was founded in 1887 as a resort community for snowbirds to escape the brutal winters. Originally called Lakeview in 1858 and later Osceola in 1870, the founders, Loring Chase and Oliver Chapman, developed the community into an aesthetically beautiful haven.
The construction of a railroad line between Sanford and Orlando led to the first Winter Park Depot in the early 1880s. Due to its tremendous success, the city experienced a population boom, attracting wealthy Northerners, and increased tourism in the area. A new station was built in 2014, serving local SunRail commuters and Amtrak passengers. I have never ridden the SunRail train, but it’s an inexpensive way to access the city if you prefer to leave your car at home.
One of the best ways to learn the history of this charming European-style community is on the Scenic Boat Tour. The one-hour cruise takes you on a journey through the history of Winter Park. You’ll travel across three tranquil lakes and glide through connecting canals. Witness sprawling lakefront estates, century-old oaks and cypress trees, and a plethora of wildlife in the area. This guided tour is the most popular attraction in Winter Park, and I highly recommend it.
Aside from the boat tour, get acquainted with the city by checking out the downtown district and local attractions! For Winter Park, this means spending Saturday mornings at the Winter Park Farmers’ Market. Here, I enjoy shopping for locally made goodies and freshly cut flowers for a picnic in a nearby park. Don’t leave without getting a bag of kettle corn, it’s a must-have treat at the market.
Speaking of parks, the city has several noteworthy parks offering unique and beautiful natural environments. For peaceful strolls through tranquil gardens of blooming azaleas and scenic waterways, Mead Botanical Gardens and Kraft Azalea Garden are at the top of my list.
Central Park, located in the heart of the urban village, features paved walkways, natural spaces with flowing fountains, and a lovely rose garden. Families can take a break here after walking through the village or enjoy a quick snack under the sprawling oak trees. With direct views of the bustling shopping district, I especially like "people-watching" from the park and viewing the trains as they enter the depot.
If you’re seeking retail therapy, you can easily find unique items inside the upscale boutiques, specialty shops, and antique stores. Book lovers: Writer's Block Bookstore is the place for you. This indie bookstore’s mission is to be part of the community and contribute to culture and the arts and literature and reading, and it has remained true to its goal for over 10 years now.
Adventurers and water enthusiasts carve out time in your day for this unforgettable kayaking adventure in Winter Park. As you drift through the Venetian-style canals, you’ll discover what makes this charming village so unique and special.
The food scene in Winter Park is unmatched! Weekend brunches include crowds of patrons seated outside at Briarpatch, one of the most iconic restaurants in town. Their use of fresh seasonal ingredients to craft their menu is why diners keep returning for more. There are also cute little cafes, coffee shops, and bubble tea shops along the avenue that are worth visiting. Outside of the downtown district on Fairbanks Ave is arguably one of the best restaurants in Orlando: The Ravenous Pig. I love the atmosphere of this gastropub, and the Mahi sandwich with truffle fries always keeps my taste buds dancing with joy.
There is so much more to do and see in this urban escape, including visiting the Charles Hosmer Morse Museum, featuring the largest collection of Tiffany glass worldwide. Nature and art come alive at the Albin Polasek Museum and Sculpture Gardens, and you will be mesmerized after your tour. Shopping at Winter Park Village is a must, and a drive through Hannibal Square will take you through one of the oldest neighborhoods in Winter Park.
With its historic charm, natural beauty, museums, and incredible dining and shopping options, Winter Park is the true magic of Central Florida. This posh village is perfect for a day trip in Florida, whether you live in or you're visiting the Orlando Metro area. And chances are, you’ll be inspired to visit soon.