As the US dollar continues to swoon, non-US friends, colleagues, and podcast listeners are doing the math and thinking it might just be worth getting fingerprinted and photographed by US Customs in exchange for a cheap holiday. The question I’ve been asked over the past 3 months is “Where should I go?”

Not an easy question — the US is a big and diverse place. Assuming the folks asking me this question aren’t interested in “Disney World” as an answer, I thought through the places in the US that I’ve been recently and came up with a focused list — one that’s not overwhelming with choices, but will give visitors a next-level understanding of Americans.  I split my suggestions into two tiers —  3 Must-See Cities and 4 Regional Excursions.  The idea is that in a 2-week visit (remember, this list isn’t for Americans), you could hit 2-3 Must-See Cities, or 1 Must-See City with a near-by Regional Excursion.

Below is my list and a quick rationale for each choice.  While I’ve enjoyed visits to each of these cities, I’ll leave specific sight-seeing suggestions to your favorite travel guide.

First Tier — The Must-See Cities

New York City — OK, no surprise here, but it’s the only choice. If you have only one place in the US to visit, go to New York City. Food, theater, parks, music, museums, shopping, sights — it’s all there and easily accessible in a compact geographic area. The most densely populated US city, it can be intense. But you can’t know the US without visiting New York

San Francisco — Again, lots to do packed into a small footprint. It’s another intense experience, but with a completely different feel.  To understand the US, you have to understand California — the place where so many Americans have gone to re-invent themselves.  The quintessential American concept of “creative destruction” drives San Francisco and the Silicon Valley.

Chicago — This may smack of a bit of “homer bias”, but the human drama of New York and the physical drama of the California coast often crowds out consideration of Midwest, a big part of the US.  Many East Coast transplants say Chicago has everything New York does except for the neuroses.  Perhaps a bit of overstatement, but Chicago allows visitors to experience the Midwest without sacrificing any of the culture, entertainment or shopping you’ll find in New York or San Francisco.

Second Tier — Regional Excursions

Boston (New England) — Pairing a regional excursion with New York, it’s a tough choice between Boston (New England) and Washington DC (Chesapeake Bay). Boston wins out because it’s a more interesting city, it has a richer history, and surrounding New England has more diverse beauty — from the New Hampshire mountains to the beaches of Cape Cod.

New Orleans — The 1,000-mile distance between New Orleans and Chicago may stretch the term “regional excursion” — until you consider making the journey on Amtrak’s City of New Orleans overnight train.  Or you can hop a cheap Southwest flight. The mix of Southern, Cajun, and Creole cultures has made New Orleans a unique city ever since it joined the US as part of the Louisiana Purchase in 1802. The trauma of Katrina dimmed its reputation as the #1 party city in the country, but 5 years on, New Orleans throws a good time again.

Austin, TX — Texas is another unique part of the US that’s often caricatured with big hats and belt buckles. Texas brings a lot of this on itself, but it’s a more interesting place than most non-Texans think.  Ask Texans to name their favorite Texas city and they’ll say “Austin” before you finish the question.  You can crawl through the 6th Street music clubs or explore the Texas Hill Country. With a motto like “Keep Austin Weird“, how can you go wrong?

Portland, OR — The regional excursion from San Francisco is another tough choice — go south to the LA beaches or north to the Pacific Northwest.  Deciding that you need to experience more than California, do I recommend Portland or Seattle? I go with Portland (by a very slim margin) because it’s a bit smaller and feels a bit grittier — and I think the food, beer, and wine is a bit better.  It’s an excellent contrast to San Francisco’s …um… eccentricities.