New York: Doesn't matter how many times you visit New York City, you will always find something new. There's museums, sporting events, restaurants, beautiful parks, and stunning views. It's all waiting for you in New York City and no one does it quite like New York.
Washington DC: Our Nations Capitol and one of my favorite places to visit. Best yet, you can easiy do it on a budget. There is clearly tons of history and significance to Washington DC but the greatest part about it all is that the entire city is easily accessible by metro (subway trains) and all the museums are free (there might be one or two with a small admission fee but all the important attractions have zero entrance fees). DC is perfect for a long weekend getaway.
Orlando: The Theme Park capitol of the world. There isn't much else to do in Orlando but being that it is every child's dream to visit Walt Disney World, Universal Studios, or Seaworld, among the many other theme parks in Central Florida, Orlando makes my list of cities to see not only as a child, but as a grownup with children as well. And lets be honest, it's not a bad city for those just young at heart as well.
Nashville: The heart of Tennessee and truly a "Music City". The great thing about Nashville is that it is the perfect place for a long weekend but also a perfect place for a 3 day getaway during the week. This city has great nightlife with live music every night of the week in almost every restaurant along Broadway, the main avenue in Nashville. There are always concerts going on and plenty of museums to fill your time.
San Diego: One of my favorite places for a relaxing California experience. Beautiful beaches, delicious restaurants, and friendly people. I really felt the California vibe here with restaurants in nearby areas that are set atop cliffs overlooking the crystal blue waves of the ocean. The views can't be put into words. You just have to experience it for yourself. Check out the Carlsbad area while you are there and take a stroll thru Little Italy in the downtown area for a delicious dinner after you've retired from surfing all day.