Bolzano, IT to Lisbon, PT by train

I believe you'll find there are no trains between Madrid and Lisbon. Rail service between Spain and Portuagal is extremely limited. You can cross the border by train far to the west, basically between Santiago de Compostela and Porto (changing trains in Vigo, I think). Alternatively, there are buses from Faro on the Algarve to Seville. There's also bus service from Madrid to Lisbon, but it takes a long time--scheduled at 8-1/2 hours or longer, I think.

Flying is the usual way to go unless the traveler wants to see both Seville and the Algarve or both Porto and Galicia or plans a long loop trip via rental car. Cross-border drop-offs usually incur really large extra car-rental fees.

Are you planning to stop along the way for a day here and there?

What kind of suggestions are you looking for and how many stops are you planning along the way?

I believe you'll find there are no trains between Madrid and Lisbon.
Rail service between Spain and Portuagal is extremely limited. You can
cross the border by train far to the west, basically between Santiago
de Compostela and Porto (changing trains in Vigo, I think).

No direct trains, but there are two routes that are possible even if you have to change train. Either via Vigo and Porto, or via Badajoz. Which route is the best depends on what you're looking for, but Porto and Santiago de Compostela are usually more popular with tourists.

I didn't realize the Badajoz connection still worked. I checked both the Spanish and Portuguese rail websites, but I guess the issue is that it's a combination of both, and neither shows the option.

I really can't imagine doing this trip by train unless there are weeks available to allow for a bunch of worthwhile stops along the way. I don't see the point, for example, in passing through Nice and just (perhaps) spending a night there without having time for a bunch of side trips. I absolutely hate taking flights in the middle of a trip, but I'd do it here.

I apologize, as I am always told, "details".
The entire trip:
Land in Vienna, for 3 nights
Train to Innsbruck, skiing 3 days
Onto Bolzano, my access to Val di Gardena
Val di Gardena(Dololmitis) 2 weeks skiing
Back to Bolzano for train to Genoa and on to Lisbon.
Stay in Genoa nights?
Stay in Nice or Marseille nights?
Stay in Barcellona nights? skiing at Baqueria?
Stay in Lisbon nights?

Yes, there are transfers involved. I thought a Eurorail Pass would solve those problems.

I thought this route, as opposed to air, would be an adventure. I was just curious if anyone had travelled this route or the best bars in the previously mentioned towns, that serve Patron.

Thanks again,

Colin

Very few people would follow that route by train, but we certainly have folks here who've been to those citeis (probably not a lot to Genoa). You may need to make separate posts in the various country forums to get info on bars, etc.

You still haven't told us how much time you have.

That sounds like an adventure! Lots of skiing too. Looks like your time is pretty generous and flexible. I think you'll find Patron in most of the big towns, but that is a specific ask. : )

I've done trips like that.

One issue that you will find it that in Spain/Portugal they do not really have the concept of a train network. The idea of using multiple trains to get from A to B is unknown, so if there is no direct train there is no train. I once stood in the station of a small town in Galicia and wanted a ticket to Barcelona, only to be greeted with "there are no trains to Barcelona from here..."

But with a bit of persistence, and the internet, you can go far. In my case my route was (after having arrived on a sailboat) Vila Garcia de Arouse - A Coruna - Barcelona (on the Trenotel, that still existed then) - Valence - Geneve - Bern...

Only the Barcelona - Valence - Geneve section I had bought in advance.

It is going to be trivial all the way to Madrid. From there I would suggest you go to Vigo or Santiago (unfortunately this no longer gets you a ride on one of the weirdest trains in Europe) and then down to Porto and Lisbo. Porto is definitely worth a stay.