Central Florida’s Hidden Gem: A City Brimming With Old-World Charm, Culinary Delights, and Natural Beauty

On a lovely spring morning, I strolled through the enchanting Kraft Azalea Garden in the village of Winter Park, a hidden gem near Orlando, Florida. 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. Years ago, I fell in love with this vibrant community, and after spending the day here, I rediscovered why I was initially smitten by this Central Florida gem.

If you want a taste of “Old Florida,” a day trip to Winter Park will feel authentic and surprisingly rare. It’s only 15 miles from Orlando, so it’s an easy detour while you’re here.   

Why Winter Park Is a Hidden Gem Near Orlando 

As I stood in awe, admiring the Exedra, an ancient Roman-style curved pavilion, at Kraft Azalea Garden, 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, I found myself believing I was hundreds of miles away from home. Welcome to Winter Park, a hidden gem near Orlando, Florida. This gorgeous lakeside community is 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. 

On my leisurely walk along Park Avenue, the cobblestone, tree-lined “Main Street,” I felt like I was browsing through 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.   

Yes, the town is vibrant, and the streets are buzzing with traffic and locals, yet Winter Park feels genuine and timeless, far removed from the popular tourist spots in Orlando that I am used to.

History of Winter Park

True to its name, Winter Park, Florida, was founded in 1887 as a resort community for snowbirds to escape the brutal winters up north. 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 native wildlife in the area. This guided tour is the most popular attraction in Winter Park, and I highly recommend it. 

Best Things to Do in Winter Park for a Relaxing Day Trip

I can't call myself a history buff, but Winter Park is a town where history awaits around every turn. As I wandered through neighborhoods with European-style homes, lined with century-old oak trees and lush, manicured gardens, I couldn't help but wonder who lived inside them. I could tell by the design of the historical houses that they were built over a hundred years ago, and they're nothing like the ones in the subdivision I live in.

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. When I first moved to Florida, I visited this campus a lot, but never appreciated how beautiful the grounds are.

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. Although I skipped the canal ride on my day here, I would recommend it, especially if you're not from the area. You'll get to learn the history of the community as well as see the beautiful homes along the waterway.    

Adventurers and water enthusiasts, you might also enjoy this kayaking trip in Winter Park. As you drift through the Venetian-style canals, you’ll discover what makes this charming village so unique and special. Aside from the water activities, 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 enjoyed shopping for locally made goodies and freshly cut flowers for a picnic in a nearby park. Don’t leave without a bag of kettle corn; it’s the most delicious treat that I get from 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 my top two choices. 

Central Park, located in the heart of the urban village, features paved walkways, natural spaces with flowing fountains, and a lovely rose garden. On my visit, families, teenagers, kids, mature folks, and people from all walks of life were enjoying the park. It's a great spot to take a break 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 liked "people-watching" from the park and viewing the trains as they entered the nearby depot. 

Strolling Park Avenue: Shops, Cafés, and Local Charm

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 cute indie bookstore has been a gathering spot for locals for over 10 years now. 

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 (well, it's on my list): The Ravenous Pig. I love the atmosphere of this gastropub, where locals in the know come to eat. Here, the Mahi sandwich with truffle fries is my go-to order. It always keeps my taste buds dancing with joy; be sure to order it and thank me later. 

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. After browsing along Park Avenue, I ended my day with a drive through Hannibal Square, one of the oldest neighborhoods in Winter Park. 

Is Winter Park Worth Visiting for a Day Trip?

With its "Old Florida" charm, natural beauty, museums, and incredible dining and shopping options, in my eyes, this community is a true Central Florida gem. The 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. It's an easy 15-minute drive from downtown Orlando, and I would recommend the free parking near the train depot. For a unique trip, take the SunRail from downtown; the ride is scenic and costs less than your favorite Starbucks drink.

If you like Winter Park, then the next time you're in the area, drive to Lake Mary, another small town near Orlando. It's a quaint destination known for its artsy vibe and festivals. Or check out these Florida hidden gems locals love. And you'll also want to check out the Visit Florida tourism page to find more towns offering a different side of the Sunshine State.