Go to Winter Park! Park Avenue has nice upscale shopping, a beautiful grassy park, great restaurants (try 310 Park South), and some neat wine bars. The Wine Room is my favorite- google it to get an idea of why it is unique.
New Smyrna Beach is my favorite beach. It is northeast of Orlando, about 45 mins away. There are some awesome restaurants there (The Garlic, Riverview, Norwood's, Spanish River Grill) and of course beach bars (Tony & Joe's is the BEST- they usually have a band playing). Cute boutique shops down Flagler Ave. The sunset is always pretty (of course the sun is to the west-behind you- but the eastern sky has the prettiest colors).
I grew up in Sanford, which is about 20 mins north of Orlando. Lake Monroe has a pretty harbor and is a nice place to watch people, boats, and birds (and alligators). They recently added a walkway on the shore with huge swings. We used to take a picnic or get a bucket of chicken and eat by the lake.
If shopping is your thing, Orlando has a huge selection. There are 2 HUGE outlet malls (touristy but you can find great deals). The Mall at Millenia is our upscale mall (think Neiman Marcus and Bloomingdales)- fun to go to just for people/celebrity watching.
Hope that helps a little. Have fun!



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Corny or not... it was still interesting



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