Kayaking in Winter Park, Florida through Lush Hidden Canals
Are you looking for a unique outdoor activity in Orlando that most tourists (and even locals) don’t know about?
While most people know Winter Park for its beautiful Park Avenue shops, historic homes, and Rollins College, there’s an entirely different side of the city hiding just behind (and under) the streets!
Scattered throughout Winter Park are several connected lakes, linked together by narrow canals filled with lush tropical plants, bamboo, palm trees, and waterfront homes.
The best way to experience this hidden side of Winter Park isn’t by car — it’s by kayak!
My parents, my husband, and I recently crossed kayaking through the Winter Park canals off our Florida bucket list, and I honestly can’t believe it took me over eight years of living in Orlando to finally do it!
If you’re looking for a peaceful adventure that feels like a completely different side of Central Florida, this guide will cover everything you need to know, including a detailed map with the kayaking route!
How to Visit the Winter Park Canals
The most common launch point for kayaking the Winter Park canals is Dinky Dock Park.
This small lakefront park sits right next to Rollins College and is just a few minutes away from Park Avenue. It’s surprisingly peaceful considering it’s right in the middle of the city!
The parking lot is extremely small, but there is a garage right behind it for the college that a lot of people use (that’s what we did).
Once you get to the park, there’s a small beach area and a public boat ramp where you can launch kayaks and paddleboards from. If you have your own kayak, you can bring it and launch here for free!
This is where most kayak rentals and tour companies operate out of as well, which we will cover in the next section!
Renting Kayaks
If you want to explore the canals on your own like we did, the easiest option is to rent kayaks from a local operator.
We personally used Peace of Mind Kayaks and had a great experience! I gave James the owner a call and arranged a meeting time a few days before. We paid $55 for a double kayak for 3 hours!
There aren’t too many kayak rental companies around the area unfortunately, as tours are more popular.
Kayak Tours
If you’d prefer to explore with a guide, you can also book a clear kayaking tour through Get Up and Go Kayaking Winter Park.
Guided tours are a great option if you’re visiting for the first time or don’t want to worry about navigating the kayaking route yourself.
The guides lead you through the lakes and canals while also sharing information about the history of the area, the homes along the lakes, and the local wildlife!
This can be a really fun option if you’re visiting Orlando and want a more structured experience.
Boat Cruises
Another popular way to see the canals is on the Winter Park Scenic Boat Tour.
This historic boat tour has been operating in Winter Park since the 1930s and follows a similar route through the lakes and canals that you’ll follow kayaking. Tours run every hour between 10am – 4pm.
The 1-hour tour takes place on a pontoon-style boat and includes narration about the history of Winter Park and the beautiful homes along the shoreline.
We actually saw several of these boats while kayaking through the canals. They’re surprisingly large compared to the narrow canals, which made for some funny moments where we had to pull our kayaks off to the side to let them pass.
While the boat tour is a great option if you prefer to sit back and relax, kayaking gives you a much more peaceful and immersive way to experience the canals, in my opinion!
Where to Kayak in Winter Park Florida
I’ve created the below map to help you understand the layout of the Winter Park Chain of Lakes and where the two main canals are!
You can save this Google Map to help you navigate along the way, and I’ll also explain the route below (with pictures!).
Lake Virginia to Fern Canal
Once you launch your kayak from Dinky Dock Park, your journey through the Winter Park lakes begins on Lake Virginia.
From the launch area, start paddling east across Lake Virginia to reach the first canal, which connects Lake Virginia to Lake Osceola. On Google Maps, this is labeled the Lake Virginia–Lake Osceola Canal, or Fern Canal.
Or, if you want to extend your kayak time, you can explore around Lake Virginia first!
It will take 5-10 minutes to reach Fern Canal from Dinky Dock Park. You may see several of the Winter Park boat cruises heading for the canal as well!
The wide open lake narrows into a small canal surrounded by lush tropical landscaping. Bamboo, palm trees, ginger plants, and thick greenery hang over the water. It’s absolutely stunning!
After a few minutes, you’ll reach the Osceola Avenue bridge, which crosses directly over the canal entrance.
Follow this canal as it winds through the neighborhood until it eventually opens into Lake Osceola, where the next part of the route begins.
Lake Osceola
Lake Osceola is a large lake in Winter Park that’s shaped like a bow (see map above for what I mean!).
When you exit Fern Canal, you’ll enter the lake on the southwest side. From here, you can technically paddle either direction around the lake, but the shorter route toward the next canal is along the right shoreline.
As you paddle along the edge of the lake, you’ll pass beautiful lakefront homes with large backyards. We saw lily pads, turtles, and fish along the shoreline – so beautiful!
Follow the right shoreline until you reach the point where the left shoreline is closest (the center of the bow). Here, you can cross the lake and continue paddling north.
On the north side of the lake, you’ll find the entrance to the second canal (see photo below!).
Lana’s Tip: Look for the giant house with a huge faucet water feature pouring into the pool (you’ll see what I mean when you get closer..haha). The entrance to the canal is a few hundred feet to the left of that house.
Venetian Canal
The second canal is often called the Venetian Canal, and in my opinion, it was the most unique part of the entire route!
If you’ve seen pictures of Venice canals — either in Italy or California — you’ll understand the name right away.
This canal is longer than the first one and has more homes along the water. Many of them have small boat houses built right over the canal, with kayaks, jet skis, or small boats stored inside them.
The canal itself is still very narrow, and the landscaping here is incredible. Palm trees, bamboo, and tropical plants surround the canal. It felt like we were paddling through a ride at Universal because of how enclosed and scenic it was.
At the end of the canal, you’ll exit into Lake Maitland.
Lake Maitland and Dog Island
Lake Maitland is another large lake that sits between the border of Winter Park and Maitland.
When you exit the Venetian Canal, you can paddle straight out toward the cypress trees in the middle of the lake or continue along the shoreline for a longer paddle.
Once you reach the cypress trees, you’ll see Dog Island in front of you as well.
When we visited on a beautiful Saturday afternoon, there were several people hanging out around the island with their dogs. Some had arrived by boat, while others came by kayak or paddleboard.
It was a fun and lively scene with dogs running around and people relaxing by the water!
If you still have energy, you can continue exploring Lake Maitland. Otherwise, this is the perfect turnaround point before heading back the same way you came.
How Long Does Kayaking in Winter Park Take?
One important thing to remember about this route is that it’s an out-and-back paddle, not a loop.
Once you reach Lake Maitland or Dog Island, you’ll turn around and kayak back through the same lakes and canals to return to Dinky Dock Park.
For us, it took just over 1 hour to paddle from Dinky Dock Park to Dog Island at a moderate pace.
The return trip took about the same amount of time, so we spent just under 2.5 hours total on the water.
Your timing may vary depending on your paddling speed, route, and how often you stop to enjoy the scenery or take photos!
Is Kayaking in Winter Park Worth It?
After living in Orlando for more than eight years, I honestly can’t believe it took me this long to finally kayak the Winter Park canals!!
While I love the classic Orlando activities like Harry Potter world, this is a completely different vibe.
Here, you’re surrounded by tropical plants and beautiful homes tucked along the lakes. The canals make you feel like you’re paddling somewhere far away from the city!
If you enjoy kayaking, scenic neighborhoods, or just discovering hidden spots around Central Florida, kayaking in Winter Park is absolutely worth adding to your bucket list!
And if you’re looking for other places to kayak around Orlando, check out my guide to Wekiva Island here!
