The communities of on the northern outskirts of Orlando are located right next to one another, and both offer their own bit of Old Florida charm. Maitland is actually one of the oldest incorporated communities in Florida, but much of its history has been overtaken by its growth as a bedroom community. The town’s “cultural corridor” gives a glimpse of its foundation and personality.

Winter Park, established as a planned community for wintering members of the New England elite, has been far more fastidious about maintaining its history. Its thick canopy of oak trees hangs over brick-lined streets, hiding expansive mansions and the upscale shopping and dining of its downtown area.

Many visitors to Winter Park choose to drive in and walk around the Park Avenue area and then stop in some of the nearby museums and art galleries. However, a fun way to get a peek at some of the town’s historic homes and beautiful scenery is the Scenic Boat Tour (312 E. Morse Blvd., 407/644-4056, www.scenicboattours.com, 10 a.m.–4 p.m. daily, $10 adults, $5 children, children under 2 free), which takes passengers out onto the chain of lakes that wend through the city, offering a backstage view of the truly impressive residences that line them.