Winter Park Lakes - Flat Water Paddling

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Paddling the Winter Park Chain of Lakes from Dinky Donk is a 4.2-mile classic Florida paddle with lots of neat channels worth exploring.

Written by

Jessica Cichra


4.2 miles

Destination Distance From Downtown

12.6 miles


2 of 5 diamonds

Time To Complete

1 hours

1-2 hours


All Seasons

Dog Friendly


Fees Permits


Land Website

Winter Park Lakes



One of the best spots to go Stand Up Paddleboarding in the Orlando area is on the Winter Park chain of lakes in Winter Park, FL. Public lake access is from Dinky Dock at Ollie Avenue, Winter Park, FL at Lake Virginia. We personally like to put in at Dinky Dock (only 10 minute drive from downtown) as it offers a nice out and back route with Dog Island as a halfway point to break or swim. It's best to go early (before 8am) or at sunset, as parking spaces in the lot are limited (you can find street parking a short distance away). 

What Makes It Great

Dinky Dock has a nice beach entry with a swimming area, public dock, boat ramp, and beautiful shady cypress trees. It's nestled within historic Rollins College and is a family friendly area. The water is clear, and along the paddle, one can view pristine private estates. The route is 4.2 miles from Dinky Dock, paddling left to the first venetian-like canal leading to Lake Osceola. These canals are the most memorable features of the route, as they are narrow, winding and canopied with a tropical landscape. 

You can paddle to the far end of Lake Osceola where you will enter another venetian-like canal leading to Lake Maitland, or you can paddle to the far end of Lake Maitland where you can round Dog Island and then pull into its cove for a quick dip or refreshing break. This is your halfway point from which you take the same route back. You must also beware of tour/fishing/ski boats that travel down the canal as well, pulling into sparsely positioned boat slips to let them pass by.

Who is Going to Love It

The whole area is very family friendly and the short route makes Winter Park Lakes fun for everyone.

Directions, Parking, & Regulations

There is a small parking lot at Dinky Dock and street parking on Ollie Ave. The park closes at dark.


Winter Park Lakes

Orlando, FL,
28.593998, -81.344719

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