If you are looking for great food, cobblestone streets, and shopping, I would recommend Park Avenue in Winter Park. You MUST try Briarpatch for brunch (get reservations), Barnie's for coffee, Matcha K (inside the store Klassy) for matcha, and Bosphorous (Turkish cuisine) or Prato (Italian) for dinner. There is also a boat tour (Scenic Boat Tour) that takes you around the beautiful lakes and teaches you about the history behind Winter Park. The address above sends you to a nearby public parking lot that is a short walk from Park Ave.
If you are located more west of Orlando and looking for the same vibe as Winter Park, then I would recommend Winter Garden. There is also tons of good food, cobblestone streets, and cute shops. You MUST go to Riley's favorite cafe and bakery called Rosallie and try their Centre sandwhich and pastries. For dinner, I would recommend Mangoni (Italian) and try their pizza! The address above takes you directly to Rosallie, but there is street parking all along the strip to park.
New Smyrna Beach is our go-to beach that is about an hour away from Orlando. Flagler Avenue is a strip of beachy shops and food we walk to from the beach. The address above is to Riley's favorite acai bowl food truck you MUST try!
There is also all the theme parks in Orlando! Magic Kingdom, Hollywood Studios, Animal Kingdom, EPCOT, and Universal.
If you enjoy canoeing or kayaking, you would LOVE Wekiwa Springs State Park. The park has kayaks and canoes for you to rent and take out if you are looking for a fun afternoon activity enjoying nature.