I’m going to throw the door wide open here. I’m thinking about my 2009 vacation schedule and trying to think of where I want to go and when.
Here are my usual spots.
I’ve spent plenty of time in Ft. Lauderdale and most of Florida.
Here are a few spots I’ve thought about.
Washington, DC
Tons of stuff to do there.
That is a consideration.
I’m thinking one East coast trip, one midwest or Deep south trip, and one West coast trip.
I was last in DC in 1994, so I’m sure it has changed. I guess Spring or Fall would be the best times to visit?
We’re going to Key West next June.
I haven’t been to Key West, but I’ve also thought about it. My mom lives in Ft. Lauderdale, so I could combine that type of a trip. I’m not sure about the opportunities for any outside activities though. Are there any beaches suitable for swimming? I wouldn’t mind going fishing, but I’m thinking the cost would be astronomical there.
The Black Hills and Badlands, South Dakota. Fun hiking, caving, beautiful scenery.
Portland, Oregon and surrounding areas. In fact, pretty much all of Oregon is kind of interesting. I haven’t spent as much time there as I’d like, but I was pleasantly surprised by how awesome I thought it was.
I’ve thought about Oregon as well.
I know the microbrew and brewpub scene there is good. There has got to be some good hiking opportunities with the Cascade mountains.
That’s what I was going to say - there’s nothing like it anywhere on earth as far as I’ve seen.
ETA - also, I spent two weeks in Maine last year, one of them spent learning to sail a schooner. Maine is AWESOME. It’s one of the few places I’ve visited that I’d like to live in (well, in the summer - don’t know if I could handle a Maine winter!) But it’s incredibly cool.
Reno, Nevada. You’ve got the casino atmosphere of Vegas (scaled down by a factor of 1000 or so) with nicer weather and more stuff to do outside. There are a couple of good breweries and brewpubs in town, and you’ve got easy access to the Tahoe basin for great hiking, fishing, skiing, or boating, depending on what time of year you come. If you’re not into the mountains, you can head northeast towards Pyramid Lake and the high desert instead.
QFT. We drove down the Oregon coast this summer, and it was stunning. We actually started in Seattle, through Portland, and over to the coast, and had a fantastic time.
Next summer, we’re planning to do the same thing, but we’re going to stay longer in Portland and drive the coast a lot more slowly. Portland was fascinating and just really cool, with all sorts of old brick buildings and neat neighbourhoods - definitely worth exploring.
The coast itself was spectacular, with incredible tide pools and hundreds of islands covered with sea birds. We walked along the beaches for hours. There were lots of places to hike in both Oregon and Washington, so you should be very happy there. Both are beautiful states, but Oregon was my favourite.
How long do you have and what do you like to do?
We visited Flagstaff, AZ this summer and loved it. It’s a very mellow town, with cool museums, good food, and lots of great hiking nearby. One of the unexpected highlights for me was the Lowell Observatory where Pluto was discovered. The Southwest is visually just an amazing place, unlike anywhere else I’ve ever been.
I’m going to pimp out my own hometown of Asheville, NC, too. (Hell, in this economy, I’ll take every tourist dollar we can get.) It’s in the Blue Ridge mountains (IMO, the most beautiful place on Earth) and there are tons and tons of hiking, rafting and mountain biking opportunities. There’s a very cool music and arts scene, *fabulous *restaurants, and six microbreweries (Highland, Pisgah, Asheville Brewing, Green Man, French Broad, and Wedge Brewing) in town.
And the Biltmore estate.
My folks take their RV out every summer, and they absolutely love the West. Arizona, Wyoming, Colorado, Monument Valley, Carlsbad Cavern, the Grand Canyon…they are awestruck.
I spend plenty of time in Flagstaff and love it. There are very few place in the Southwest I haven’t been.
Hiking is very important. Any city with good hiking is likely to get some serious consideration.
As far as your Deep South leg goes, I’d suggest the older “walking cities” of the South: New Orleans, Charleston, Savannah and St. Augustine. These are all great especially if you like history. Charleston and Savannah can be done together since they are so close to each other. St. Augustine will give you a different view of FL from the beaches and amusement parks we are so known for…well that and our wacky voting and our love of constitutional amendments. 
Everyone should see New York City at least once in their lifetime.
Memphis is great for a music-themed vacation.
If you want to go to the Midwest (particularly Wisconsin) you can go online (I’m sorry I can’t remember where) and find a “brewery tour” of Wisconsin. It goes from the Miller brewery in Milwaukee (kinda southern Wissy) and you wind your way all the way up to Chippewa Falls where Leinenkugel’s is brewed (WAY north Wissy), all the while stopping at little microbreweries all along the way. It’s more of a “road trip” type vacation, but hit the state at the right time, and Mid-Northern Wisconsin can be BEAUTIFUL!!!
(Also: Milwaukee county zoo is one of the best in the nation, Brewer games are always fun to go to, especially tailgating…and a lot of times there are a lot of random festivals going on which are always fun)
Do like any type of music in particular? Almost every Colorado Ski town has a music festival of some kind in the summer, and often several. Jazz, Bluegrass, Dixieland etc. Lot’s of sweet mountain hiking, biking,fishing(although out of state licenses can be expensive if you arn’t really into it). Fi you have freedom of dates, figure out what you like, then see what festivals there are for it.