Winter Park, Orlando guide

One of the area’s most unique features is the Winter Park Chain of Lakes, a series of six lakes connected by canals. You’ll find locals and visitors on the water paddle boarding, kayaking, water-skiing and fishing. Want to learn more about Winter Park’s waterways and wildlife? Book a spot on the popular Scenic Boat Tour.

Don’t let the frosty name fool you — Winter Park is packed with green spaces. Kraft Azalea Garden and Mead Botanical Garden are favourites for a scenic stroll. And Ward Park’s sports and athletics facilities always attract an active crowd. But the most popular green space of the bunch is Central Park, which hosts the weekly Saturday farmers market.

Winter Park was developed in the late 19th century and retains much of its original architecture, particularly around the Park Avenue district and Hannibal Square. Rollins College is one of Florida’s oldest institutions of higher education, dating back to 1885. And the Casa Feliz Historic Home Museum is a restored 1930s Spanish-style farmhouse designed by architect James Gamble Rogers II.

Bring the family to Cady Way Park for its softball fields, playground and pool. Or spend an afternoon at the Howell Branch Preserve, which has a boardwalk, play area and an observation deck overlooking the wetlands. With the Winter Park Chain of Lakes offering water sports and boat tours, there’s plenty to keep all ages entertained.

Dive into the past at the Winter Park History Museum, or learn about the area’s historical African American community at the Hannibal Square Heritage Center. One of the best art museums in Winter Park is the Rollins College Museum of Art. Or visit the Charles Hosmer Morse Museum of American Art, which celebrates the art and designs of artist Louis Comfort Tiffany.

Some of the best restaurants in Winter Park are located in the Park Avenue district. You’ll find everything from Michelin-recognised eateries to international cuisine and alfresco cafes. On Saturday mornings, dozens of vendors sell fresh goods at the farmers market in Central Park. It’s a great place to pick up picnic supplies before heading to the park.

The Park Avenue district is the place to go for a night out on the town. With its taverns, wine bars and cocktail lounges, you’re guaranteed to find a spot to quench your thirst. Feel the urge to move your feet? Downtown Orlando’s dance clubs are just a 20-minute drive away.

You’ll want to save room in your suitcase when visiting Winter Park. The area’s independent boutiques and brand-name shops are one of its biggest draws. Explore the Park Avenue district with its one-of-a-kind boutiques. And spend an afternoon browsing along the shaded walkways of Winter Park Village, an outdoor shopping arcade with restaurants and a cinema.

Winter Park hosts a diverse calendar of events. Visit in March for the annual Winter Park Sidewalk Art Festival, which debuted in 1960. You can also catch more art at the Winter Park Autumn Art Festival, which is dedicated to regional artists. If you’re a fan of classical music, join the Bach Festival Society’s annual event, which started in 1935.