Guest blogger Nakiesa Faraji-Tajrishi shares her tips for spending a picture-perfect day in the charming city of Winter Park, including outdoor adventures, dining and more.

I spent my childhood growing up in downtown Orlando. As I got older, exploring the city and its surrounding neighborhoods became a passion of mine. One neighborhood that always reminded me of a little slice of Europe right here in Central Florida was Winter Park.

Discover: Things to Do in Winter Park

With everything from the plethora of street shopping and acclaimed restaurants on Park Avenue to uplifting galleries and museums, and gorgeous hidden parks to canals that rival the beauty of those in Europe decorated in the natural landscape that screams “quintessential Florida,” Winter Park truly has a little bit of something for everyone. Only a short drive from downtown Orlando or a 45-minute drive from the theme parks, this unique city feels like a world of its own.

To help you make the most of your time in Winter Park, I’ve compiled a curated list of some of my favorite places to see and things you can do for a day. I hope you enjoy these tips!

Historic Hannibal Square

Got a morning to spend in Winter Park? My first recommendation is the idyllic, historic Hannibal Square. A quiet and compact street just blocks from centralized Park Avenue, Hannibal Square feels cozy. With its brick-lined streets and cute cafes, it’s worth the short walk just to experience the area’s ambience. (Editor’s note: Hannibal Square played a significant role in Central Florida’s African American history and culture, which you can learn more about at the Hannibal Square Heritage Center.)

Discover: African American History & Culture in Orlando

We headed to CFS Coffee Shop, a Colombian cafe born of the coffee-bean farmer passion of the Andes Mountains. Beyond an incredible cup of coffee, CFS offers healthy breakfast and lunch options. Since it was early in our day, we chose to grab some breakfast. CFS has a varied menu giving you so many tasty ways to start your day, from traditional Columbian breakfast arepas to more health-conscious options like tofu scrambles and protein smoothie bowls, and crowd favorites like avocado toast.

After looking over the menu, I went with the berry oatmeal bowl, topped with almond butter and a cup of the farmer’s choice coffee (complete with brown sugar cane, cinnamon and cloves). My friend ordered a baked chicken empanada and a ham, egg and cheese breakfast sandwich on ciabatta bread.

Since it was such a nice day outside, we took our meal on the smaller tables that lined the street and had fun catching up while watching the cars and people pass by. For those who prefer indoors, the seating inside the cafe is cozy with lots of tables, a couple outlets and free Wi-Fi to get your work done.

Normally when I come to this cafe, I grab a corner and stay for a few hours. The staff is amiable and will answer any questions you may have — as well as share the best way to brew the perfect cup of coffee.

Winter Park Farmers’ Market

On the weekends, there is nothing quite like stopping by the Winter Park Farmers’ Market and its many vendors. Since 2020, the market has been held outside in Central Park West Meadow. Located right by the train station at the corner of New York Avenue and Morse Boulevard, the market is open every Saturday from 8 a.m. to 1 p.m. It’s also dog-friendly, so bring your favorite furry companion along for the sights!

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There are a few rules to follow if you want to bring your pup, like we did with our 5-month-old mini schnauzer:

  • Avoid crowded areas
  • Provide 10 feet of space between your pet and others
  • Leash must be 4 feet or less
  • Clean up after your pet
  • Be up to date on vaccinations
  • Aggressive pets may be asked to leave
  • No dogs inside the buildings or on the patio area

Winter Park Scenic Boat Tour

Next on the agenda was something a bit breezier and a whole lot cooler: a ride on the Winter Park Scenic Boat Tour. Family owned and operated since 1938, this is the perfect attraction for someone who is interested in seeing the idyllic Winter Park Chain of Lakes and its beautiful canals, brimming with cypress trees, local flora and fauna, and a taste of real Florida wildlife.

You will occasionally see fish, birds and, if you’re lucky (or not so lucky depending on your point of view), an alligator, but those are harder to come by in the lake these days. Admission is normally $14 for adults and $7 for children, and reservations are recommended. When I went, every tour for the day was completely sold out! The boat leaves every hour on the hour and runs from 10 a.m. to 4 p.m.

A leisurely ride of about an hour, the tour takes you through three of the seven lakes that make up the Winter Park Chain of Lakes. The tour guides are retired Winter Park residents with a passion and desire to share their wealth of knowledge about this community and homes within. Guests flock from all over the world to see the canals and learn a bit more about this community, which feels so different from the rest of greater Orlando’s metropolitan area.

You would be hard-pressed to find a more relaxing and amusing way to spend an afternoon, surrounded by beautiful homes and lush canopies, and filled with neat tidbits about the history of Winter Park, which at one time was considered the edge of the Florida frontier.

Tour guides point out houses of well-known celebrities, share facts on local museums (including the days you can visit), and give a complete history of the rise of Winter Park as a community. The tour even passes by Rollins College, and you will have the opportunity to get a glimpse of the campus from the boat. The tour guides are also knowledgeable about the wildlife typically seen in the area, such as anhingas’ mating behaviors.

As if all that wasn’t enough, we passed through the canals four times on the journey, giving you one of the best views of the entire tour. Often you will see other smaller boats and kayaks on the water, and it gives it a very neighborly feel that is Winter Park. With a bit of humor, lots of interesting facts and a mix of recommendations of local sights, it’s easy to see why this is one of the highest-rated attractions in the Winter Park area.

Gorgeous Public Parks

My personal favorite end to any day would be a trip to one of Winter Park’s hidden yet absolutely stunning smaller parks. Here I have two recommendations. One would be to spend the afternoon wandering Mead Botanical Garden, and the other to watch the sunset at one of my favorite spots in Winter Park, Kraft Azalea Garden. Both parks are open from 8 a.m. to sunset and offer free admission.

Discover: Orlando Public Parks

Mead Botanical Garden

Tucked in a sleepy corner of Winter Park on Denning Drive, Mead Botanical Garden is easy to miss but well worth seeking out. There are 47 acres of gardens for you to explore, with a rose garden, butterfly garden, lovely picnic spots, hiking trails, boardwalks, greenhouse and ponds teeming with life. You could easily spend a couple hours there exploring the grounds, getting lost in the sights and sounds of natural Florida.

A quick look to the left as you enter the park will reveal a small clearing with a flower garden. One of my favorite spots in the park, I knew it was the perfect place to sit and read a book, enjoying some snacks with my friend. We brought along some croissants and fresh juice from the ingredients gathered at the farmers’ market and enjoyed the feeling of the warm Florida sun under the shade of the tree canopy.

Since there was an ongoing event for March this year, we knew we needed to be out of the park by 5 p.m., so we limited our exploration to the flower and rose garden. Just past the initial cluster of flowers that are visible from the road, through the ivy-wrapped gate, lies a hidden rose garden, shielded from onlookers and the road.

As we enjoyed our stroll through the flowers, we noticed that many people were placing fallen roses on the statues that adorned the walk. That inspired us to find some fallen flowers of our own for a few cute photos. We placed the best of the flowers we found at the foot of the statue and took a quick walk to the nearby lake before the park closed for the day.

Kraft Azalea Garden

This has been my go-to date-night spot for years. Once you see it for yourself, you’ll understand why. Situated behind the open-air Winter Park Village shopping and dining hub, and almost an afterthought in the quiet neighborhood street (Alabama Drive), Kraft Azalea is stunning year-round.

Kraft Azalea Garden provides incredible views of the sunset over the lake and the perfect opportunity for a breathtaking end to your day. We were particularly lucky on this day, as it was finally spring and the azaleas were in full bloom.

There is a cute colosseum next to the waterfront that is my favorite sitting spot, but since it was such a beautiful day, that area was already occupied, and we wanted to maintain a safe social distance. Luckily, it’s hard to find a bad view, and we were easily able to set up our little blanket amongst the azaleas and cypress trees. We sat enjoying our snacks and some fresh air, feeling blessed to witness the sun shimmering through the moss, feeling absolutely at peace in the quiet and secluded park that has always held a special place in my heart.

It was a heartwarming and beautiful conclusion to the perfect day around Winter Park — an oasis of beauty nestled unsuspectingly in the middle of central Florida.

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