One of the defining features of most of the travel I've taken in the last few years has been the limitations on it. I worked at Caterpillar, and they allowed me two weeks of paid vacation per year - and the few times I requested unpaid vacation (or a pay cut in return for two more weeks of vacation) it was denied. So that meant that I had to fit whatever I wanted to do in a given year into 10 days off or less. And honestly, I think that's part of what made the travel I did as awesome as it was.
Many of my vacation days disappeared for random things over the course of the year. Every year included a day off for Summer Camp festival, and a few years included a day or two off to go down to Florida over MLK weekend to visit my sister. Sometimes there were vacations that I "had" to take - people I hadn't seen in a while, or trips I've had planned for a while. I went to Florida for Thanksgiving one year, which used three days, and went to France another which used half my vacation for the year, and went to the Philippines to visit a friend last year, which was half as well.
So that meant that if I wanted to travel otherwise, I had to do my best to not use any vacation days. But rather than letting that limitation become something that made me decide not to travel as much, I made it work. I'd go to a concert in St. Louis or Des Moines or Chicago on a weeknight, and drive back the same night. I'd get back at 3am, sleep til 6am, and then go into work exhausted. I've told people that one of the best things about Peoria is how easy it is to leave - Chicago, Des Moines, Milwaukee, Madison, Chicago, and Indianapolis are all within 4 hours. To most people, that means it could be a weekend trip. To me, that means I can leave after work and make it to a concert, and make it back in time to get a few hours of sleep before the next day.
I did weekend road trips too, of course. To most people, the places I went would be far enough that they'd fly, and probably take some vacation to make it a week-long trip (or more) as well. But if you have to leave Friday afternoon, get to an airport, go through security, fly, and get out of the airport somehow to a hotel or a friend's place, you're not really saving that much time over driving.
Driving was tons cheaper as well. I wasn't poor with the job I had, but there were other things I wanted to spend my money on, so I tried to travel cheaply if possible. With a car that gets 30mpg and gas around $4 gallon (worst case scenarios for my car and the gas price), it's still only $60 a person for two people to drive 1000 miles, which will get you to Minneapolis and back. Get more people in the car and it's cheaper. Gas was only about $40 a person when I went to Tallahassee and back.
So I'd usually leave after work on Friday, drive around 12 hours, sleep, spend 12 hours in a city, sleep, and drive 12 hours back. And because I was willing to do that, I got to see Denver (and a concert at Red Rocks), Minneapolis (only 7 hours, so an easy trip), New York City, Washington D.C., Asheville N.C. a number of times for concerts, Charleston S.C., Tallahassee for a frisbee tournament, New Orleans twice, Kansas City, Nashville, and a bunch of other places. Not many people can say they've been to all of those.
And honestly? The limitations make the story that much better. "I took a vacation to New York" sounds cool, but a lot of people have done it. "I drove 12 hours to New York and back in a weekend" is a story that not very many people can tell. If not many people can say they've been to all those cities, I bet that no one from Illinois but me can say they did weekend trips to all of those places.
And when I did actually have vacation - for example, when I had a week of layoff back in 2009 and decided to go to 7 concerts in 7 different states in 7 days - I still put limitations on it. I didn't want to spend much, so I slept in the back of my car, and showered in truck stops. And it's a much better story than if I'd stayed in a sterile hotel that was exactly the same in every city. I still remember what the rest stop on the way to Asheville looks like, because there are almost no rest stops for 100 miles before that, so it was a welcome sight, even if it had lights on all night long that made it hard to sleep.
On this trip, as much as it'd be cool to stay for longer in each place, it's kinda cool to be in and out. I have a few hours in some cities, and maybe a few days in some of the bigger ones, so I have to choose carefully what I'm going to do, because I probably can't do everything I want. But the story is that much better. "I've been to all of the states" is cool. "I've been to all of the states, on my motorcycle, in a single summer" is way better.