travel in comfort to Italy

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Milan is usually inexpensive as an entry airport for Italy from here on the west coast. From PDX there are roundtrip flights during December/January for about $500. The most convenient ( though maybe a bit more expensive) Milan airport to fly into is Milan Linate.

Genoa is a 90-minute train ride from Milan’s central train station.

Oregonian here, Monty. We like to fly Condor direct to Frankfurt or British Air direct to London. Sometimes it works best to fly out of Seattle but going over water from the west coast to Europe certainly is efficient. We also like to spend a night or two on arrival and then proceed by train to the real starting point of our trip, in your case, you might fly to FRA, recover for a night or two, then proceed by train to Genoa. Check Bahn.de to determine feasibility. I hate flying when I can take a train even if it takes longer by train.

Here's your biggest issue: Unfortunately, some of your stated preferences are directly in conflict, specifically "most comfortable" and "not horrifically expensive." Those two things are pretty much diametrically opposed to each other. You are going to need to set priorities, and start thinking about what's really necessary (to you), rather than what's just "nice to have", and what's completely unacceptable, rather than what might be tolerable annoyances you could live with. Sliding scale for everything.

Hard truth: The less you spend, the less comfortable you are going to be. This is pretty much a cut-and-dried, hard, cold fact, unless you have some magic or luck you can rely on.

Conversely, the more you spend, the more comfortable you might be. This one is a little more squishy, because it's possible to spend a bunch of money and still not be super comfortable, but it's generally true that spending more typically gets you more comfort - but the devil is in the details. And you gotta pay attention to the details.

Your itinerary, the airline you fly on, layovers, and other factors can move the needle a bit, but the overwhelming hard reality is going to be, the less you spend, the less comfortable you are probably going to be.

The airlines have this figured out. Prices are based, to a large extent, on making customers as miserable as they will tolerate at a given price point. Then, you can pay progressively more and more to buy your way out of some of the things that make you miserable. EG, a nonstop flight costs more than a flight with multiple stops. Crazy routings with long layovers is the low-priced norm. Pay more to eliminate some or all of those things, and you'll probably be at least somewhat less miserable. Pay more for extra seat room. Pay a lot more for a business class lay-flat seat that makes sleeping easier for many of us.

At least you are going in the winter. You will save money by going when few others want to go. So avoid going around major holidays (travel around Christmas is expensive, crowded, and generally horrible IMHO - New Years, too). A week into January would probably be better because of less demand.

I know, not what you want to hear, but it's the reality for us all.

Good luck.

Most comfortable? Fly Business Class.

The only fast choice from Portland (PDX) to Genoa (GOA) is with KLM with one stopover only in Amsterdam (AMS).

Comfort is mostly dependent on the class of service you purchase. First class will be more comfortable than Economy, but it will also be pricier.

What makes a flight particularly miserable for you? You say you are rather small, so you probably do not need extra legroom (unlike my 6 ft 4). Do you sleep easily on a plane? I don’t, so I prefer day flights if I can get them. They are boring, but sleeping is a nightmare for me.

If you want to go through immigration only once, avoid London - not EU or Schengen, so double immigration. It is also a fairly expensive city.

I was at both Amsterdam and Frankfurt, and they should be manageable - in particular if you do not have to change flights. And despite the cliché, both Germans and Dutch will most likely help you as good they can, and should speak decent English. Both cities should also work fine for a little relaxing off the jet lag.

Generally speaking, both flights and big city hotels should be cheaper on weekdays, so flying on a Tuesday or Wednesday might be worth considering.

We are about the same age as you and still do tourist. We do book so that we can choose our seats. I always do an aisle and wife does window.

Monty OP--

Yes, we are of the same ilk. I'm only 68 but didn't do European travel until I was 53 (4 Euro-trips since), and back then in 2010 I was a lot more tolerant of 'challenging' travel conditions than now. From Portland (or from my friend Laurel's Forest Grove, OR) it must be a bear. From Chicago it's really not that bad, 7-8 hours to the European hub city, then a 2 hour break--which I actually like, usually Frankfurt or Zurich--then a couple hours to destination. I actually would rather do a short (but not too short!) stopover than nonstop direct, and oft times it's less expensive as well. I feel 2-3 hours layover is about perfect, gives you a little leeway time if the overseas flight is late. Foreign airports, if you have the time, are fun to roam in...

But it's the airline's creature comforts--or lack thereof--that is really getting to me these days. Yes, I'm able to stand it, but you know, since COVID you can't really get up, walk around, stand back by the flight attendants and BS with them. That kind of thing makes the flight go faster. I can't sleep on a plane, and no knockout drops either! Either seats are skinner, or I'm going the other way. So...I'm actually thinking, as value-driven (cheap) as I am, how can I get the best deal I can for business or 1st class, and be able to justify the added cost in my own mind? I don't really travel much so I can't build up points.

Not to hijack, but any tips on getting a good deal on business/1st class without spending 2K person extra?! Did it once, Chicago/Frankfurt...and it was worth the $800 apiece we spent...until we were in the last 30 minutes, and I say, why did we spend the money??!! Hah. We're mostly Lufthansa or SwissAir people, they ain't perfect but better than most on international flights. Oh, never been to Genoa but I think we're headed there on our upcoming trip in March 2027. Good luck to you!

Hey, Monty,
Is your timing flexible? Have you heard that Alaska Air will begin to fly non-stop from Seattle to Rome, starting in May? No details as yet, but they are one of my favorite lines. I’m hoping for good business class prices when they launch the new route. I suspect you know that they run multiple cheap flights between pdx and Seattle. I’m hoping to get an a.m. flight to Seattle and then a straight shot to fco. Rome to Genoa should probably be done by train.