The Winter Park Chain of Lakes comprises six major bodies of water joined by a narrow system of canals.
In a lush urban setting from downtown Orlando, The lakes are a favorite location with people who boat and paddlers, especially during the weekend.
Although this 4.5-mile stretch between the lakes is publically accessible from various locations, the most convenient spot to launch and with the best view to launch from is Dinky Dock Park.
It’s located in the downtown area of Winter Park next to Rollins College. The parking space is tiny, and it is recommended to arrive early or go on the trip on an off day.
Clear Kayak Through The Winter Park Chain of Lakes
Venetian-style canals run through the picturesque Winter Park Chain of Lakes!
Welcome to the picturesque historic, beautiful city of Winter Park! Your journey across this part of the Winter Park Chain of Lakes begins on the shores of Dinky Dock Park, nestled right near Rollins College. The trip will take us through three of the seven lakes for about two hours.
Your guide will meet you on the shore, ready to meet everyone, and explain the basics of the kayak before putting everyone in their kayaks. When everyone is set to begin, it’s time to get going! If you’ve selected for the Sunset Paddle, we’ll be paddling our way to our seats in the front row to the most stunning sunsets you can see in the entire city. If you’ve chosen our glow-in-the-dark tour, We’ll illuminate the night with LED-lit kayaks!
We begin with Lake Virginia, where your guide will start with paddling tips and fun facts about this university and lake! After a few minutes of the paddle, we’ll arrive at an insignificant waterway gap leading us to The Fern Canal. The Venetian-style canals we’ll travel through on tour are filled with lush vegetation and trees, while the canopy of Spanish Moss provides natural shade that will keep us cool throughout our travels. The canals were once utilized as a means of transportation for logs. During the glow tour fishing, the fish will chase the light fixtures, and it is common to see them following the journey by the sides of the illuminated kayak!
The canal is where we paddle, and we are at lake Osceola, the largest of the lakes we paddle. While enjoying the beautiful open water, the guide will show you and provide information about Winter Park’s fauna, flora, and the incredible million-dollar homes that line the lake’s shores. We’ll travel through a vast field of flowering lily pads, which can be observed through transparent kayaks. Bird lovers rejoice! You’ll see various flying creatures during the trip: the Herons, Egrets, and even Anhinga’s love of flying to make appearance.
Lake Maitland is the largest of the lakes within the chain, with 449 acres. It is located in Winter Park and Maitland to the north. The only exclusive areas sharing these lakes are the Isle of Sicily and the neighborhood referred to informally as The Vias. Canals joined Lakes Maitland, Virginia, and Osceola and were waterways used for the logging industry during the city’s beginning. The Fern canal is the one that connects Lakes, Virginia, and Osceola; it’s also known as the Venetian Canal, which provides access to Lake Osceola and Lake Maitland.
In second place in terms of size, Lake Maitland is Lake Virginia at 225 acres and is located within the town’s limits. Along the shores of this Lake is Rollins College which has one of the most stunning campuses in the nation. Students who co-ed at Rollins can enjoy living near the lake, which is a breeze to access boating, water skiing, and paddle boarding.
Lake Virginia is home to the sole lakeside park within the city. It’s located on the northern shores of Lake Virginia, also known as Dinky Dock Park. The park has a sandy shoreline, boat launch, and dock.
Lake Virginia is also home to one of Winter Park’s best-known historic residences and estates: Wind Song. The first house was constructed in 1938, and the property is managed through Rollins College. The property is now a nature preserve and home for the peacocks that came to the region in 1950.
Fern Canal – Lake Osceola
Through Fern Canal to Lake Osceola. Glimpse Albin Polasek Museum and Sculpture Garden from the lake. The Winter Park Scenic Boat Tour is also a popular excursion, departing at Lake Osceola. Be wary of these large tour boats on narrow canals. Even smaller kayaks might have to reverse towards a more spacious passing point that is part of the adventure.
Lake Nina – Lake Minnehaha
A canal off Lake Maitland runs past Lake Nina (the smallest of the lakes) and eventually Lake Minnehaha. The canal runs alongside the bridge on Horatio Avenue. You’ll see a bike trail that is integral to the Maitland Bike Route.
Winter Park Chain of Lakes – Resources
- Dinky Dock Park Boat Ramp Public
- Dinky Dock Park – City of Winter Park
- Fort Maitland Park Boat Ramp Public
- Winter Park Scenic Boat Tour