The city of Winter Park, located just North of Orlando is well known for it's arts and culture, festivals and parks, and boutique shopping. It is also host to the Winter Park Art's Festival, which attracts artists from all over the world.
There are plenty of family activities, such as the famous boat tour on Lake Virginia. You may want to visit Cady Way Trail for a bike ride or hike, and Central Park to relax. Mead Garden is also good for quiet relaxation and birding. Winter Park is also quite pet friendly and has it's very own dog park at Lake Baldwin.
For culture seekers, there is Rollins College, Creadle School of Art, Charles Hosmer Morse Museum of Art, and the Cornell Fine Arts Museum.
Park Avenue has an impressive collection of boutiques, for an eclectic shopping experience. Stop by Antiques on the Avenue, and Timothy's Gallery which features unique art and jewelry.
Make sure you don't miss the Winter Park Farmer's Market, which is the largest in the area. This is every weekend.