Guide to Winter Park, Orlando
Take a break from the amusement rides to explore Winter ParkOriginally established as a refuge from New England winters in the late 1800s, Winter Park has evolved into a year-round getaway. While just a stone's throw from Orlando's bustling theme park scene, Winter Park offers a more tranquil retreat with acclaimed restaurants, local shops, green spaces, and lakes featuring boat tours.
Welcome to Winter Park, a sanctuary originally established as a winter refuge for affluent industrialists in the late 19th century. Positioned just 20 minutes northeast of Downtown Orlando, it offers an inviting respite from the area's bustling theme parks, while providing visitors with more than enough activities to fill their vacation time. Amble down the charming cobblestones of Park Avenue, the city's vibrant epicenter full of standout restaurants, unique boutiques, and engaging museums. Nearby, a prestigious liberal arts college infuses the town with a cultural pulse. For a more active afternoon, head to the stunning chain of lakes that offer opportunities for boating, swimming, kayaking, and paddle boarding. The town of 30,000 promises a captivating blend of culture, leisure, and scenic beauty. In this guide, we will discuss how you can make the most of your next vacation to Winter Park.
Getting to Winter Park
Reaching Winter Park from Orlando International Airport is fairly straightforward. The most convenient method is to rent a car or hire a taxi or rideshare service. Winter Park is 15 miles north of the airport and the drive typically takes about 30 minutes depending on traffic. Shuttle vans provide another option that could prove to be more cost-effective than taxis or rideshares. Depending on which hotel you are staying at, your hotel might offer free shuttle rides to and from the airport.
Public transportation is also an option. Take Lynx Bus #11 or Bus #51 from the airport to the downtown Lynx Central Station, then change to Bus #102 to Winter Park. This journey takes about two hours.
Central Park
Give yourself time to stop by Central Park. Known as the crown jewel of the local Park’s Recreation department, the lush canopy of trees provides ample shade, making it great for picnics, leisurely strolls, or people watching, even on warm summer days. A captivating rose garden adds a dash of romance for couples who are on vacation.
Throughout the year, Central Park hosts events such as art festivals, outdoor concerts, and seasonal celebrations. Its proximity to local shops, cafés, and cultural attractions makes it a must-visit destination for travelers seeking a blend of relaxation and urban exploration. Additionally, it serves as a great spot for children to burn off any pent-up energy.
Kayak or paddleboard
Embrace the outdoors by kayaking or paddleboarding the picturesque chain of lakes strewn through Winter Park. Connected by human-made canals, these lakes offer a tranquil, scenic paddle journey within an urban setting, making it a popular activity for anyone who loves to be on the water. Whether you’re a seasoned paddler or a novice, exploring these placid waterways offers an immersive way to take in the city’s natural beauty. Local rental shops and guided tours are available to help you make the most of your experience.
Book a boat tour
The holiday season transforms Winter Park into a wonderland that's particularly enchanting for families with children. During the first weekend of December, “Winter on the Avenue” turns Central Park into a magical holiday spectacle complete with the lighting of the Christmas tree and menorah, a parade with more than 70 years of traditions, and snow slides.
For those who prefer a leisurely lake experience without engaging in sports activities, consider booking a boat tour. Discover Winter Park’s history, admire the area’s luxurious homes, and possibly spot an alligator or two, all from the comfort of a pontoon boat. Operating since 1938, Scenic Boat Tours offers hour-long guided cruises through the region’s lakes and canals, providing visitors with an off-the-beaten-path experience in the heart of Winter Park. Throughout the journey, knowledgeable tour guides highlight local wildlife, share historical insights about the city and lakeside homes, and sprinkle the tour with entertaining facts about the area.
Museum hop
If you are in Winter Park on a Saturday, be sure to check out the Farmers’ Market. It is located in an old train depot and full of local vendors selling delicious kettle corn, fresh juices, and gorgeous flowers.
Winter Park is home to a rich assortment of galleries and museums for visitors to explore. Begin your cultural exploration at the Rollins Museum of Art, which offers free admission and showcases over 5,600 artifacts from ancient to modern periods. Continue your artistic journey at The Charles Hosmer Morse Museum of American Art, home to the world’s most extensive collection of Louis Comfort Tiffany’s masterpieces.
Nearby, the Albin Polasek Museum & Sculpture Gardens feature an impressive showcase of the eponymous sculptor’s work. Lastly, explore the Hannibal Square Heritage Center to learn about the district’s origins as a vital African American community. Established in 1881, Hannibal Square witnessed one of the earliest Civil Rights marches in 1887 and is now among Winter Park’s most affluent areas.
Where to stay in Winter Park
Winter Park does not have the extensive selection of hotels and resorts found in the neighboring areas. What it does have is a small-but-mighty list of charming accommodations that complement its scenic locale. The Alfond Inn stands out with its curated art collection and luxury amenities. The stylish boutique hotel is ideal for travelers seeking a sophisticated stay. Park Plaza Hotel, a 28-room historic boutique hotel, blends modern comfort with old world European elegance. Sitting on Winter Park’s fashionable Park Avenue, an abundance of dining, shopping, and cultural attractions are just steps away from its door.
Who should stay in Winter Park
Winter Park is for every type of traveler; however, the idyllic neighborhood definitely provides a romantic backdrop for couples seeking a memorable getaway. Its tree-lined avenues, charming boutiques, and Venetian-style canals set a picturesque stage for love. Delight in a romantic dinner at The Ravenous Pig or Prato. For an adventurous date, Get Up and Go Kayaking offers guided sunset tours through Winter Park’s “Chain of Lakes” in clear kayaks, or spend the afternoon walking hand-in-hand through the blooming flowers at the Mead Botanical Garden.