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Must-See Places in Florida: The Winter Park Canals

a tree next to a body of water

Winter Park is a city near Orlando, famous for its beautiful outdoor spaces, including stately trees, abundant parks, and the Winter Park Chain of Lakes. Although the city is mainly known for its six vibrant lakes, including Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha, it’s the man made canals that connect them that make Winter Park and Maitland so special. 

Whether you’re into watersports or just love traveling and exploring new places, the Winter Park canals are one of the absolute must-see places in Florida. 

The Perfect Getaway for Watersports Enthusiasts 

The City of Winter Park dates back to 1885 when it was built as a resort community around a chain of beautiful small lakes. Florida was becoming a winter getaway for the northern elite, and Winter Park developed accordingly. Many high-profile people, including past presidents, frequented the city and vacationed at its opulent lakefront resort hotels.

To facilitate drainage and enable boat traffic, canals were dug between several of the lakes. Although the waterways between the lakes are quite narrow, they offer some of the best kayaking in Florida. 

Straight out of a storybook of fairy tales, these striking Venetian-style canals lead through lush greenery that creates an enchanting surrounding. Many visitors cross the city’s bridges without noticing the beautiful canals beneath which is unfortunate given that they are considered one of the must-see places in Florida. 

When kayaking down the otherworldly scenic route of the Winter Park Canals, it’s not uncommon to spot otters, kingfishers, bald eagles, woodpeckers, ospreys, wading birds, and waterfowl. Birdwatchers particularly enjoy the 5.22-acre public Kraft Azalea Garden Park, located on the shore of Lake Maitland, as it is home to many nesting birds during hatchling season. 

The Winter Park Chain of Lakes also draws fishing enthusiasts to its 2,781 acres of water. They can expect to catch sunshine bass, striped hybrid bass, bass breams, gar, or tilapia. 

Since there is limited public access for fishing on the shoreline, many opt to use a kayak or canoe to reach the area’s best fishing holes. The deepest spot of the lakes can be found in the 29-foot hole on Lake Maitland. Anglers like to come here in the early morning to catch their fish before the watersports enthusiasts occupy the lake. 

Things to Do in Winter Park Florida

a building with a store on the side of a road


While its hidden canals are an absolute Florida must-see, Winter Park offers a number of other captivating attractions and cultural events. For example, the Bach Festival Society at the local Rollins College organizes an annual concert series as well as the yearly Bach Festival. 

In the city, you can find other must-see places in Florida, including the Mead Botanical Garden which boasts nearly 48 acres of different eco-systems that feature flowers, a butterfly garden, an amphitheater, and a recreation center. 

You may also visit the Charles Hosmer Morse Museum of American Art where you can marvel at the largest collection of Tiffany glass art in the world as well as other American art collections produced in the 19th and 20th centuries. 

The home and artworks of the famous Czech immigrant sculptor Polasek can be found in the Polasek Museum & Sculpture Gardens on Lake Osceola, and, as a must-visit for car enthusiasts, the Winter Park Concours d’Elegance Exotic Car Show displays rare luxury cars and attracts more than 10,000 attendees every year.

Considered one of the best of its kind by various national magazines, the Winter Park Sidewalk Art Festival is one of the country’s oldest outdoor juried art festivals and draws thousands of visitors every year. 

Aside from unique shopping and dining experience, Winter Park also offers a charming Farmer’s Market, which serves residents and visitors with fresh produce and baked goods every Saturday. 

Adventure Kayaking in Winter Park 

graffiti on a brick building

Twisting and turning through whimsical tropical surroundings, the Winter Park Canals offer an off-the-beaten-path adventure with some of the best kayaking in Florida. The ideal times to visit are the early morning hours when the water is still, the air fresh, and the temperature is not too high, or in the early evening when the sun sets and transforms the area with a golden glow. 

However, without a map, you can easily get lost. A guided tour will ensure that you make the most of your trip to one of the must-see places in Florida. 

Winding through the Venetian-style canals, you can expect to be met with lush plant life on tropical terrain, countless Instagrammable moments with views of the city’s statuesque mansions, as well as some of Florida’s finest flora and fauna. You’ll likely encounter plenty of fish, birds, and other wildlife, no matter what time of day you visit. 

Whether you decide on a calm morning tour or a romantic sunset trip, your kayaking adventure is sure to be unforgettable, as the Winter Park Canals are truly one of the must-see places in Florida

a man riding on the back of a boat