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Orlando to Winter Park - A Happy Tail

A road trip of a lifetime from Orlando to the town of Winter Park.

By Miriam Porter Wheels.ca

Nov 6, 2015 5 min. read

Article was updated 7 years ago

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There is no denying it’s officially getting colder and darker earlier in Toronto since Daylight Savings. If your family is starting to crave more sunshine perhaps it’s time to visit the sunshine state. Nicknamed for it’s tropical climate, humid temperatures, and average 230 days of sunshine, Florida is the perfect place to visit for a break from the long cold Canadian winters. It’s the closest American state to the Tropic of Cancer and the Equator, so pack a bathing suit and get ready to have fun outdoors.

Map from Orlando to Toronto

If you choose to drive to the sunshine state, check out my article that offers tips and tricks for families making the road trip down. Top Ten Things To Consider Before Your Florida Road Trip With Kids as a parent, Orlando seemed like the natural city to pick since it’s home to so many majestic theme parks. When my son, Noah, learned about our next traveling adventure he quickly picked Disney World as our first adventure. It was easy to agree to this, after all, who doesn’t love a mouse dressed in clothes that calls himself Mickey? The excitement begins the moment we drive up to the massive welcome sign.

Disney Land

We check into the Swan and Dolphin Hotel and immediately switch our boots for flip-flops. This landmark hotel is located on the Walt Disney World Resort and great for families of all ages. They boast five swimming pools, a water slide, tennis courts, game rooms, a children’s activity center, swan paddleboat rentals and multiple delicious restaurants to choose from. That evening we enjoy a delicious buffet dinner in the Garden Gove. Within minutes Pluto and Goofy show up with hugs, smiles and magic!

Swan and Dolphin hotel

The next day we head out to the happiest place on earth, Disney World , the flagship home to the magical empire. From our hotel there are three ways to get there; boat, shuttle or simply walk along the boardwalk towards Epcot. From there you can choose which theme parks to visit and ride the famous monorail to your destination. We decide to spend the day among our large furry character friends at the Magic Kingdom. Noah and I are immediately greeted by huge chipmunks – Chip and Dale. Our magical journey continues for another 12 hours (Yes, that’s right) and we have one of the best days ever.

Chipmunks in Disneyland

Many families explore Disney for multiple days since there is seriously so much to see and do. However, what many people don’t know is that only a short road trip away is a serene, quiet and quaint little town called Winter Park – away from all the hustle and bustle. So the next day we set out for our Winter Park road trip, about a 45-minute drive north of Orlando.

Orlando to Winter Park Map

The Interstate 4 will take you there and is the highway that cuts Florida in half and runs from Tampa to Daytona Beach.

Upon arrival Noah is confused and asks, “Where is all the snow?” For him winter means snow, but here in Winter Park it’s a beautiful sunny day! This adorable old town is home to 70 parks, nature trails, museums, outdoor patios, boutique stores, restaurants, bike rentals, and a picturesque train station.

train station

We decide to explore nature and sign up for a Scenic Boat tour. This off the beaten path adventure is located on Lake Osceola and provides guests with guided cruises through various lakes and narrow canals along the Winter Park chain.

Scenic Boat tour

Our friendly captain, Charlie, tells us all about the history of Winter Park, which happens to be Central Florida’s oldest community that was founded by wealthy Easterners in the 1800’s. Noah stares up at the dangling tree branches hanging over the water and Charlie explains it’s Spanish Moss, an air plant. We pass a 275-year-old Oak tree, bamboo, lily pads, and even glide by “Mr. Rogers” old house. Perhaps you watched Mr. Rogers Neighborhood growing up and remember the man with the cardigan and sneakers that delighted children for decades from the land of Make Believe!

Canal Boat Tour

After the tour we make our way over to New York Ave to have brunch at Ethos Vegan Kitchen. The completely vegan menu features healthy home-style food and we both order the pumpkin pancakes. They are delicious!

 On the way out Noah spots a huge display of fancy cookies and we bring some with us to explore more of Winter Park.

The tree-lined streets are packed with people and dogs enjoying the day and relaxing with a coffee or meal. We stop and pat several curious dogs and chat with the friendly locals.

Winter Park's Tree lined streets

In fact, there are so many dogs that we start noticing stores dedicated just to dog supplies.

Noah has always wanted a dog and today is no exception. I explain to him the dogs are not up for adoption, they already have a home. But moments later Noah runs up to a whole group of dogs gathered outside a store. There are big dogs, small dogs, old dogs and young dogs. And wouldn’t you know it, they are all up for adoption! It turns out Orange Country Animal Services, Furever Friendz, and VIP Rescue of Central Florida are having a dog adoption today in Winter Park (What are the chances?) Noah immediately makes friends with all the furry pups with happy wagging tails and we spend time patting and getting to know them.



Although we didn’t adopt a dog that day we did have a wonderful time exploring Winter Park. Now onto our next adventure!

All photos taken by Miriam Porter

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