Winter Park shops

Orlando was just a small town surrounded by orange groves until Disney arrived, but Winter Park has been a haven for snowbirds for almost 150 years. Established in 1885, it was the first planned community in Florida where shopping, culture and restaurants were centralized and neighborhoods were created in the nooks and crannies of ancient live oaks. Today, Winter Park is still well known for its upscale neighborhoods and small town feel.  Spend a day and enjoy the simple pleasures of family time among the beauty and nature of Winter Park.

Alcoves hide trinket treasures and dining delights

At the heart of Winter Park is Park Avenue. Eclectic shops intermingle with name brands like William and Sonoma and Gap. Cafes offering continental and international cuisines line the main street and are hidden treasures in picturesque alcoves. Luma on Park is a favorite with its seafood courses and Bosphorus serves Turkish cuisine. Wine bar hopping is more common here than beer guzzling, and with Luma, The Wine Room and Eola Wine Company all next to each other, it’s a delicious way to spend the afternoon people watching.

The Wine Room

What seems like a small community is very proud of its cultural attributes. Art galleries are scattered between Park Avenue and Hannibal Square, and well known museums are within easy walking distance. At the south end of Park Avenue is Rollins College, a private liberal arts college sprawling on the shores of Lake Virginia. The Cornell Art Museum houses a permanent collection of European and American paintings, bronze sculptures and artifacts from the Middle East to Native American Indian, plus showcases rotating collections. On the north end of the commercial district of Park Avenue is the Morse Museum, home of the largest collection of Tiffany glass. Past Rollins is the exquisite lakeside sculpture gardens of the Polasek where every April it sponsors the Winter Park Paint Out.

The Polasek Museum and Sculpture Gardens

The Winter Park community is active in many events throughout the year. The St. Patrick’s Day Parade features Irish music and dance and Mickey Mouse and Santa Claus make a special appearance during the Winter Park Christmas Parade. During the second week in December, residents with watercrafts line up their lighted vessels for the nighttime Winter Park Boat Parade on the three main lakes. In the winter, an ice skating rink is set up for some holiday fun, and in the spring, artists and bon vivants flock to the many festivals showcasing different art mediums and chef creativity. In fact, the Winter Park Sidewalk Art Festival is the nation’s largest and oldest juried outdoor art festival.



For a relaxing tour of Winter Park from the water, visit Scenic Boat Tours at the end of Morse Blvd. The captains are quite knowledgeable on Winter Park history, even the gossipy bits. At the north end of Park Avenue is the Winter Park Golf and Country Club where a round of golf is another way of touring the suburbs. The speed limit is no more than 30 miles an hour, but it still seems too fast to really appreciate the mansions and beautiful landscaping on the twisting shaded streets of Winter Park. Kraft Azalea Park is the best place to enjoy a picnic on Lake Maitland while watching Rollins crew row and families learning to paddleboard. The Exedra Monument is a popular place for photography and weddings.

The Exedra Monument in Kraft Azelea Park


Most major airports have direct flights to Orlando and Winter Park is located just 35 minutes from the Orlando International Airport (MCO) and 45 minutes from the major attractions.  A magical community in itself, Winter Park embodies family togetherness, home-grown, and natural. For moore information on Winter Park events, visit