The Winter Park Chain of Lakes consists of six main bodies of water tied together with a system of narrow canals.
In a lush urban setting just north of downtown Orlando, the lakes are a popular destination for boaters and paddlers, particularly on the weekends.
While this 4.5 mile route between the lakes is publicly accessible from several points, the easiest place to launch with the best scenery is Dinky Dock Park.
It is in downtown Winter Park next to Rollins College. The parking area is small, so it’s best to arrive early or take on this paddling trip on a weekday.
Resources for exploring the area
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Location: Winter Park
Length: 4.5-mile round trip
Trailhead: 28.593890, -81.344665
Address: 410 Ollie Ave, Winter Park, FL 32789
Restrooms: At Dinky Dock Park
Land manager: City of Winter Park
Open 8 AM to 8 PM. Shade is very limited. Bring plenty of water and sun protection.
From Interstate 4 in Orlando (north of downtown) take exit 87 for Winter Park. Head east on W Fairbanks Ave for 2.2 miles, then turn right onto Ollie Ave. Parking is at the end of the street, adjacent to a boat ramp.
The beach at Dinky Dock Park provides a perfect launch point, about 50-100 feet south of the parking area.
Immediately after entering the water, swing to the left and follow the shoreline past several private docks.
In 0.2 mile, a brown sign for Fern Canal sits under a stately live oak covered in Spanish moss.
Turn left into the canal, while taking caution of boat traffic on this narrow waterway.
Aptly named, this canal is lined by hundreds of ferns and various decorative landscape plants.
Huge oak limbs carpeted with resurrection ferns arch overhead before the canal passes under a road bridge and emerges at Lake Osceola.
Navigation on the open water can be tricky. It’s best to follow the shoreline to the right, gliding next to patches of water lilies until reaching a beachy point in another 0.4 mile.
Crossing a narrow strait in the lake, follow the shoreline to the left for 0.4 mile before arriving at the Venetian Canal.
Turn left onto this waterway, again being cautious of boat traffic. Bananas, palms, orchids, and gingers bordering the canal establish a lush tropical setting.
The Venetian Canal is noticeably longer than Fern Canal, continuing a quarter mile before opening to Lake Maitland near the Kraft Azalea Garden.
Floating alongside this beautiful public park, note how tall cypress trees hug the shoreline, towering over shell walkways and benches.
Head northward towards the next landmark, a small lone cypress tree where the lake narrows between two points.
A large nest sits on top of this ornament-adorned tree, a popular spot for waterbirds such as anhingas to roost and dive for fish.
Look northwest. A tree-covered island stands prominently in the lake’s center. A straight paddle to Dog Island from the small cypress is about a half mile.
Land on the shoreline of Dog Island at its beach. Wear shoes if you leave the boat to walk its network of trails, as there was broken glass in the water and on the shore.
Leaving Dog Island, head back across Lake Maitland by paddling towards the small cypress before crossing to the opposite end.
Watching other paddlers and boats can be helpful to locate the entrance of the Venetian Canal on the southern shore.
Exiting the Venetian Canal, cross Lake Osceola by keeping the shoreline to the right until passing between the points, then keep the shoreline to the left.
The Fern Canal is very visible after 0.8 mile. After a short cruise through this canal, turn right and follow the shoreline back to the Dinky Dock beach.
More worth exploring while you’re in this area.
Established as a camellia showcase, this public garden has a nature trail first built in 1956 to explore natural habitats within a 47-acre urban forest.
Fifty acres of formal gardens hug Lake Rowena in this historic display of botanical diversity in Orlando.
A maze of paved trails provides an urban hike through hammocks of ancient live oaks and natural green spaces at this City of Orlando park.