Step 1 - Have money
For example:
San Francisco <-> Milan, May 7 - May 20, Norwegian Air+Easy Jet: $598.
Air Bnb for the duration: Central Loft, $70/night, 13 nights, $910. (you can find much lower as well, if you want to go for the minimum).
Shop local, cook & eat in the apartment, $20/day? $280.
Spend 13 days walking and exploring Milan for under $2,000.
That's not a trivial amount, but it's not the $2,000 air fare and $150 night hotel and $50 day food type of money, either.
A lot of folks, however, aren't comfortable with putting themselves out there into an airbnb (or equivalent) and fending for themselves with local markets and transport. It's really not that hard (depending on where you go and your tolerance for embarrassment and alienation), but there's definitely a language and cultural barrier that needs to be overcome or worked around.
I think that Rick Steves, in his unique way, makes a lot of people feel more comfortable with getting out there. It really is so much better to travel without a tour company mediating the experience.
It's also not hard to get by in most places in Europe, particularly Scandanavia. Most folks there speak English, among other languages.
That's great if you are near a large city like San Francisco.
However, Madison, WI <-> Milan, May 7 - May 20, United: $1304 economy, 21h travel time.
It IS the $2000 airfare ( or approaching it).
Now, ORD <-> MIL is $687, but MSN -> ORD is at least a 2 1/2 hour trip by car, longer by bus.
It's a $60/rt ride from Madison to O'Hare on the Van Galder bus. If you drive, it's whatever cost to take your car plus at least $10/day at ORD.
I used to pay ~$1500 CAD from Ottawa, Canada to Manila, Philippines. Now that I’m aware of deals and have a flexible schedule/remote-work-policy I scoff at any trip with the same itinerary that’s > $800.
> Above all, Steves told us, do not be afraid. The people of the world are wonderful, and the planet we share is spectacular.
I've done a small splash of international travel. But in my career I've been lucky enough to be exposed to people from lots of places in the world, and I've drawn the same conclusion. When people here in the US ruminate about global events and foreigners I wonder if they've ever really met any. Because you very quickly draw the conclusion -- "Hey, these people aren't very different at all -- they have family and friends and they go to work and care about their family and friends just like me!"
For example, in the mid 90s we went to the Dominican Republic for a week, and we were oh-so-broke. We stayed in a hut (actual hut) behind a friend's house; we borrowed their bikes to go to town to buy groceries (including food items where I had no earthly idea what they were); we cooked on a tiny alcohol camp stove (and when it ran out, we discovered that the alcohol it used was a bottle of rum). We saw nothing that was a tourist destination; it was all "just folks." ...and we got a huge amount of understanding about what it meant to live in a poor country without resources.
I've also stayed in 5-star hotels in Paris and indulged myself for a week falling into every tourist vortex. That's perfectly fine, too, because it's okay to appreciate beauty. However, you appreciate it _better_ when you know its context and history; I highly recommend Rick Steves _Europe Through The Back Door_ because it gives us Americans a better sense of European history, not to mention how it affected art, architecture, etc.
Mind you, Steves' travel guides are rarely my favorites. He's not a foodie, and I regularly choose destinations based on what I can eat. And he's opinionated, which I appreciate, until we disagree on those opinions. (He's meh on the Black Forest, and it's one of my favorite places.) Then again, I'm not his target audience. I think he's a treasure nonetheless.
You might enjoy watching Rudy Maxa's cheeks instead, then.
One of the very best travel guide series is those books by Anton Krotov and friends written in Russian. While these travelers have gradually become pretty bourgeois and fans of posh train travel (which allows them to guide also ordinary holidaymakers), they spent many years traveling the world by hitchhiking, sleeping in mosques, etc. on absolutely tiny budgets (like 0–5€/day). Besides writing travel guides for the Russian-speaking market, they also do their fair share of public-speaking visits to small towns to encourage young people across the USSR and Eastern Europe to set out traveling even if they have little money.
Today if you come into contact with shoestring travelers in South America or Africa, you find that a lot of them are Russians and Poles. Their comparative poverty didn’t stop them from traveling transcontinentally, and it has always puzzled me that some comparatively better off Americans complain they can’t indulge in their wanderlust dreams due to lack of money.
Joke aside, not everyone can afford time off vacationing from work, and even with PTO covering their time off.
More discussion on that here: https://news.ycombinator.com/item?id=17778108