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A Perfect Day in Winter Park, FL: Clear Kayaking, Dining, and More!

a boat traveling across a bridge over a body of water

Winter Park, Florida, is a charming city nestled just north of Orlando, offering a delightful blend of outdoor activities, culture, and dining experiences. With its picturesque parks, tree-lined streets, and bustling downtown area, Winter Park is a fantastic destination for a day trip or weekend getaway. In this blog post, we’ll outline an itinerary for spending a perfect day in Winter Park, featuring clear kayaking on the Winter Park Chain of Lakes with Get Up And Go Kayaking, delectable dining options, and more!

Morning: Breakfast and a Stroll Through Central Park

Start your day with a delicious breakfast at one of Winter Park’s many charming cafes or bakeries. Consider stopping by The Briarpatch, a local favorite offering classic American breakfast dishes and a cozy atmosphere, or try the delicious pastries at Buttermilk Bakery.

After breakfast, take a leisurely stroll through Winter Park’s Central Park, a beautiful 11-acre green space located in the heart of downtown. Admire the park’s lush landscaping, fountains, and sculptures, and perhaps catch a glimpse of the scenic SunRail train passing by.

Mid-Morning: Clear Kayaking on the Winter Park Chain of Lakes

Next, embark on a clear kayaking adventure with Get Up And Go Kayaking, a top-rated local tour operator. Their Winter Park Chain of Lakes tour takes you on a two-hour guided excursion through the interconnected lakes and picturesque canals of the city.

While kayaking, you’ll also get to admire the stunning waterfront homes and learn about the history and ecology of the area from your knowledgeable guide. Be sure to bring a waterproof camera or phone case to capture the beauty of your surroundings, and don’t forget to wear sunscreen and a hat for sun protection.

Lunch: Enjoy Local Cuisine

After your kayaking adventure, refuel with a delicious lunch at one of Winter Park’s many dining options. For a taste of local flavors, head to The Ravenous Pig, a gastropub offering creative dishes made from seasonal, locally sourced ingredients. If you’re in the mood for something lighter, try the fresh salads and sandwiches at Power House CafĂ©, or indulge in some gourmet tacos at Hunger Street Tacos.

Afternoon: Explore the Morse Museum and Park Avenue Shopping

Following lunch, take some time to explore Winter Park’s rich cultural offerings. Visit the Charles Hosmer Morse Museum of American Art, home to the world’s largest collection of Tiffany glass, as well as an array of American pottery, paintings, and decorative arts.

Next, head to Park Avenue for some retail therapy. This charming, tree-lined street boasts an eclectic mix of boutique shops, art galleries, and specialty stores, perfect for finding unique souvenirs or treating yourself to something special.

Evening: Dinner and a Show

Cap off your day in Winter Park with a memorable dinner at one of the city’s many excellent restaurants. For an upscale dining experience, make a reservation at Prato, an Italian-inspired eatery featuring house-made pasta and wood-fired pizza. If you prefer something more casual, try The Coop, a Southern comfort food spot serving up mouth watering fried chicken and other classic dishes.

After dinner, catch a show at the nearby Annie Russell Theatre or the Winter Park Playhouse, both of which offer a variety of performances throughout the year.


With its captivating blend of natural beauty, culture, and cuisine, Winter Park, Florida, is an ideal destination for a memorable day trip. From clear kayaking on the Winter Park Chain of Lakes to shopping and dining along Park Avenue, there’s truly something for everyone to enjoy. So, pack your bags, and get ready to discover the charm and allure of Winter Park for yourself. By the end of your day, you’ll undoubtedly be planning your next visit to this enchanting city.

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