Guide to Winter Park, Orlando

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.

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.

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.

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.

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.

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.

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.