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BrieannaLenhart

Paddleboarding Winter Park Venetian Canals

Updated: Jan 1, 2023

Now the owner of an inflatable paddleboard, I was so excited for the opportunity to take my Isle Pioneer for a spin!



There are chains of lakes in Winter Park, Florida linked by these canals. You can visit these canals by scenic boat tour or booking a kayak/paddleboard tour. But with having my own, all I needed was a drop-in point.


Dinky Dock Park is a publicly accessible drop-in point for boats and other watercraft. Dinky Dock Park has a great facility. It was easy to get in and out of the water. I had plenty of space to rinse off my board using one of the rinsing stations and pack it up at the end of my excursion. There is also a minuscule beach and a small swimming area. Parking is very limited but free. The only parking for the park is the lot you see after the sign. The garage and all other parking areas are reserved for Rollins College. There is the Sun Trust Parking Garage back over by Park Avenue.


I went on a Saturday, so I had to do a few laps, but eventually, someone left. There are restrooms and a rinse-off station. I rolled out my board in the grassy area and began inflating it and putting it together. Even with using a manual pump, this paddleboard inflates quickly and is easy to put together.


Now for the fun part, dropping into the water. There is a small area for kayaks and paddleboards to drop in between the boat ramp and the beach.


It was a beautiful day out! The wind was a little strong on Lake Virginia, the lake next to Dinky Dock Park. I definitely got a resistance workout in. It was nice to see the Rollins Sailing Team putting that wind to use. It was a lovely sight.



I paddled diagonally from Dinky Dock Park towards the canal that leads you to Lake Mizell.









Coming back to Lake Virginia, keep an eye to the right you will see another canal leading you to Lake Osceola. This specific canal is one of the most iconic.





Lake Osceola had much less wind, so paddling was so smooth and easy. Coming out of the canal to the left is Albin Polasek Museum and Sculpture Garden. If you haven't visited it yet, I highly suggest you do. It is one of the first places I visited when I moved to Orlando. A renowned sculpture artist, his work is sprinkled throughout the garden of his home in Winter Park. I remember seeing the lake from his garden and such a surreal feeling a few years later to be viewing his garden from the lake.



You do have to be aware of this lake since it is where the boat tour has their boarding site. So be mindful of the rules of the waterways.


There are two more lakes connected by these canals: Lake Maitland and Lake Berry.


Another drop-in point to access the chain of lakes over by the Kraft Azalea Garden. Again there is not a lot of parking, and you will have to create your own spot among the trees. There is a dock next to the Rollins Boathouse you can use to help assist getting your watercraft in the water. This puts you on Lake Maitland.


We paddled the Winter Park Canal, taking us to Lake Osceola. The entrance to the canal is just around the dock as you take a sharp left. This venetian canal is lined the tons of tropical foliage.





You will pass under this lovely stone bridge, which guides cars on Palmer Ave over the canal.

The exit from the canal onto Lake Osceola.

Lake Osceola is a great place to watch the sunset from the water!



It was refreshing to hop on a board and get going, but if you don't have a paddleboard, you can book a boat tour or a paddleboard tour. If you are interested in booking a boat tour you can check out the Scenic Boat Tour website. Winter Park is a historic and cute town. Winter Park has been one of my favorite stomping grounds for a few years. I suggest taking a stroll down Park Avenue afterward. I work there and see it daily, but what I love with experiences like this is seeing a different side of a town. And in Florida, seeing a place from the water is part of the sunshine state magic.

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