Topic: I have something like a lifestyle SaaS business, but I'm mainly at home and take a week or two off whenever I want (and other people have time). For example, last week, I went snowboarding in France for a week.
In 2013, I spent about 8 weeks in total in other places (US, France, Italy, Belgium, Switzerland, Turkey).
In 2012, I traveled for 6 months around the world with my girlfriend.
On extended trips, when I hit Europe (and thus needed to camp at climbing areas), I'd spin the $12/day rental car past a Decathlon and pick up a $20 sleeping bag, $40 tent, and $1.99 giant inflatable pool toy mattress to serve as the envy of the entire campground. Everybody else has stoves and cookware, so that part's sorted. And when it comes time to fly home, some lucky dirtbag gets a bunch of free gear.
I'm a technical PM so I tend to have to be on site for contracts and yet to find a remote PM role. That aside though I'm getting back to more coding these days so hope to be able to work remotely in the future.
Keep in mind, that your taxable income for the year will likely be less than $20k, so most of your paycheck while you're living cheaply will go straight towards travel expenses for the next lap.
Personally, I liked 3 month contracts. I usually ended up saving a lot more than I could possibly spend on the road.
That lasted for about 10 years, but I've slowed down a bit now.
These days I seldom take more than six weeks truly "off", with all tools down and no hours billed. Instead I tend to move around to places that have the things I want to do, set up shop, and do my "vacationing" on nights, weekends, and the odd afternoon off. There are cheap-ish rental houses/apartments with good wifi pretty much everywhere in the world now. If you can work remote, I don't see any reason why you shouldn't be working remote. Like, all the time.
It actually works out pretty well this way. I get way more climbing/surfing in than I used to when I was contracting in LA to save for the next trip, and I get to have a house with an office, comfy couch, etc.
Thank you, software industry, for making us pretty much the only class of individual on the planet who can pull this off!