First trip to europe - month of September Begin in Dolomites end in Porto-

Sounds like a wonderful trip. Enjoy.

Next trip, based on what I think you are saying you enjoy, think about Montenegro (a little Italian flare, but very deep into village and nature). And very economical.

You'll probably have to do a lot of flying to make that happen, which I am loathe to do within a vacation, but I am not sure if there is enough time to do it all by train. Dropping a car in a different country incurs a large fee, but this trip is not quite long enough to lease one (as I understand it).
There are a million options, so I would sort out the Porto end and the Italy end first to see what you have room for in the middle. You could easily just wander in Italy by car, then fly to Porto and rent a car there for the Duoro valley.
I'm less well versed in northern Italy, but I've never been to any region that I was disappointed in!

Thank you - Alas this is our once so unless we win the lottery we will not be returning . Also if we do rent a car we would rent and drop off in same country, get the train across then rent on the other side. ( my son did this on a 6 week trip to Europe and said it worked out well - though they did take acouple flights ) Yes we are planning Porto and then working backward .

Kw, Sounds like a great trip, but as others have mentioned it involves some distances & plane travel days. If I'm reading this right, it's 18-19 days on the ground after the Dolomites. Then you've got 3 days of big travel. N Italy to S Spain, S Spain to Porto & I'm not really sure how long that would take, so let's say 3 days of travel. So that leaves you with 15 days on the ground.

• I've hiked in the Dolomites for a few days & stayed in huts, it's a fabulous experience & that's a great time of year for the mountains.

• The Lake District would be my pick for the next 3 days. No need for a car. https://community.ricksteves.com/travel-forum/italy-reviews/opting-for-a-lake-maggiore-stay-vs-lake-como-suggestions-appreciated
  https://community.ricksteves.com/travel-forum/italy/italian-lakes-region-idyllic-non-touristy-towns-recommendations

Personally, my favorite town in the north is still Florence, having been across most of N Italy, it deserves a few days, but you said you're not much for museums or cities, in which case check out the hill towns around Tuscany, (easiest by car except for Siena, which you can access by bus from Florence). There's a lot written on RS, has many articles on the area. Just go to the main page of RS, use search bar at top, 'Forum small tuscan towns' or 'Forum best day hikes lake district' etc. )

I've hiked part of the Chianti Classico from outside Siena, plenty of day hikes in the area. Maybe base yourselves in Siena instead of Florence OR skip to the smaller and lovely Volterra instead. 3 days would be great, or longer. I've rented cars a few times in Florence or Siena, but watch out for fees entering town centers, especially Florence.

I LOVED Volterra (rented car in Siena) & stayed a few nights, wandered around the Etruscan ruins & during the evenings it was pretty quiet. https://www.ricksteves.com/watch-read-listen/read/articles/volterra-tuscanys-top-hill-town. (So that's 6 days, leaving you 9 days...)

Transit - Unless you really want to spend a day & night on trains, maybe fly out of Milan non stop to Madrid & take the train to Granada. You will need advance tickets for the Alhambra. No comment on flights, not my bailiwick but others will have ideas. I spent a month touring Andalusia by bike and would highly recommend Granada (Alhambra), Cordoba as my second choice (Mesquita) & third on my personal list would be Sevilla. I would try to skip spending time in Madrid & Lisbon given your preferences. I think the longest part of your trip would be getting from Granada by train to Madrid & flying to Lisbon & train to Porto, which IMO is too long of a day. Ask others where to break up the trip. I too have heard wonderful things about the Duoro Valley, so you could easily spend 4-5 days in the Porto area. Good luck! You're in the right place & as you refine your trip, you can ask more specific questions on each leg.

Sandancisco,

Thank you so much for this very detailed ant thoughtful reply.

We are now looking into the train from Venice to the Lakes region and researching Siena and Volterra.
Also researching the Parque,Nacional Da Peneda-Geres in Portugal. We have visited almost every National Park in the US and many in Canada- - Outdoor fiends I guess ;)
Also, on your and my son's recommendations Sevilla, after our stay in Granada.

Thank you again

Wendy

Maremma/Ucellina park in Tuscany is fantastic and not terribly far from Siena/Volterra. You could check flights to Sevilla (and a few other airports in Andalucia, like Malaga) from Pisa. Southern Tuscany is not too far from Rome, so you could look at flying from there also. Sounds like a fantastic trip!
Near Granada you have a lot of hiking opportunity as well.

Sounds like your trip is evolving well, hopefully you can focus on the local hiking / walking in the areas where you're staying. (BTW, I bought local hiking maps once I arrived in Siena, they were much better than on-line or book descriptions of the area.). Once you decide on how long in N Italy, I would nail down flights from Pisa to Madrid / or maybe to Granada but I bet that would require a change in Madrid. (Pisa was a good suggestion above), that's certainly do-able and much closer than Milan. THEN there's that big travel day from Granada to Porto, unless you wanted to fly to Lisbon & stop nearby. Please let us all know how it goes.

There is a lot to see in Italy, but the big three are Venice, Florence and Rome. If you do those three, it will take you from 10-14 days. Take the train.

The Alhambra is in Granada and would be best to fly to Granada. Not sure of the flights from Italy to Granada. As much as I loved the Alhambra and Granada, a couple of days there is enough. You didn't mention Seville, my favorite city in Spain.

Renting a car in one country and dropping in another creates a huge drop fee, so you don't want to do that.

Trains are great in Italy and good in Spain.

If you go to Porto and do the Douro Valley, it is best to do a river cruise. We did a great one that was a week long. They are not cheap. If you don't want to do that, consider taking the train up the Douro Valley (the rails run along the north side of the river). Take the train to Regua or Pinhao or both and visit some of the many vineyards. If you go far enough you could go into Spain and see the wonderful city of Salamanca.

In Porto, we discovered the very best bed and breakfast EVER. It is called the InPatio Guesthouse. It has only five rooms, so book ASAP. It has a great location, wonderful owners and super breakfasts.

Getting from Granada or Seville to Porto by train may be complicated. We got to Porto from Lisbon, since they have a fast train.

Hello everyone and thank you for all the wonderful input.

As of now we are thinking of taking the train to Pisa and staying at a wonderful farm stay about a 2 hour drive away.
Agriturismo Il Rigo for two nights. We learned of this through looking at what other "tours" the company we booked through for our Dolomite trip offered . Anyway- then flying to Giorna and on to Granada. Fly to LIsbon train to Porto. Sightsee there, then rent a car and do a circle tour Duoro -Peneda-Gerês National Park and the coastal Minho area and Viana do Castelo.

We did like the idea of the Lakes district , which looks incredible , but thought it might be too crowded for us . But it is easy to get to from Venice !

Also , thought on e-sim cards? They sound easy and affordable. Wondering if you can call the US on them without $$$. We had a regular SIM card in NZ and used Whatsapp to contact people at home.

We have a good Medicare supplement that covers $50,000 (lifetime) emergency medical issues with a small deductible. Thinking that is enough.
Also , recommendations for travel insurance appreciated .

And definitely packing very light -
Thoughts and ideas appreciated.
Wendy

Forgot to reply to geovagriffith. We looked at your recommendation for lodging in Porto- but unfortunately all booked . We will check back though.
Thank you
Wendy

Hi again Wendy! Great you've 'taken what you liked and left the rest', there are so many different ways to travel, it's just what suits you. OK, there's a LOT on the forum about e-sims, but maybe first look at your provider. I'm happy with just Whatsapp & wifi where it's offered, & if I need to desperately call someone or more likely text, I have a plan set up on AT&T $10 per day for data access. If you have T-mobile, just search on the main page of RS & there's quite a bit about how to use their plans in Europe.

AHHH travel insurance... well this is a huge topic. You mentioned being happy with your Medicare supplement, so what other type of insurance do you specifically want? I personally have an annual "GeoBlue trekker Choice" policy (recommended by some large travel orgs like Overseas Adventure Travel), plus Medicare, plus AAA Premier (really I got it for the 100 miles of free towing, but it has some international emergency services & lost baggage etc.) .I probably have a bit too much, but it works for me & I would much rather have too much than too little. For a deep-dive, try slogging through this post.
https://community.ricksteves.com/travel-forum/general-europe/medical-insurance-tutorial-and-recommendations

For Portugal, we used Pointe de Lima as our base for day tripping in the Minho region (we had a car). Wonderful to do evening strolls at night along the river and look up at the stars. Small town, but very picturesque and on the Camino route. Don't forgot to visit Braga and Guimarães. Julie Dawn Fox blog is a great resource for the Minho region.

Another vote for Braga. One of my personal "off the beaten path" favorites.

OK Everyone - Wow such great tips for our travel
We are almost set - which is good as we leave in 10 days !
Arrive Venice- let afternoon eat , sleep - one day sightseeing - being jet lagged take the Vaporetto off and on as we see fit- Then the next day off to Corvara for a night and then on a week long village to village and refugio hike - in the Dolomites - booked through Collett's . ( Great company to work with and a huge variety of walking tours. ) End of hike - take train from Venice to Florence , rent a car and drive to Val d 'Orcia for 3 nights at Il Rigo - a farm stay - - day trips Siena, Volterra or just relax. Return car Florence and then train to Milan and fly to Madrid for two nights - with one day of sightseeing . ( time wise the best choice) Rent a car and drive to Granada , have rented a great place with a view of the Alhambra - visit Alhambra - go to National Park etc - since we could not find a one way rental in Spain ( we wanted to train to Granada , rent car , drive to Sevlile and then train to Porto but no go) - Drive back to Madrid , fly to Porto - 2 nights in Porto then we have a relative of a relative ( who knew !) who lives in Viana Do Castelo who we have been invited to stay with - then off to Peneda-Gerês National Park for three nights in a small stone cottage. Then home.
On another note - I checked with Verizon and they have a $100/mo international travel plan , unlimited talk in EU , text and 20 GB data. So I can keep my number - YAY !
I purchased Rick Steve's travel pack , so I will be carrying that, It has an amazing amount of room and compartments and my husband has a carry on suitcase .
Also , travel insurance - Our Medicare Supplement Plan F covers international medical needs up to 50K for lifetime . So we went with that esp as we already pay for it .It met with approval from the hiking company for "required" trip insurance .
I also discovered that if you are not worried about trip cancellation etc you can put in $0 for cost of trip and just medical comes up - for us ,for a month, it would have been only $100. Also, Collett's uses a travel ins company out of the UK that was very reasonable for trip interruption , baggage etc - does not cover your trip in the US. For example , our flight leaving from the Us is not covered . Was just over $400 for both of us for a month long trip , half of what I had checked on in the US You have to be between 16 and 79 -so no increase as you get older .
Am going to check out the last two suggestions in the Porto area .

Excellent! Sounds like you've really worked out a trip that suits you. (And it's so nice you got back to the Forum with your final itinerary!)

Rent a car and drive to Granada...since we could not find a one way rental in Spain ( we wanted to train to Granada , rent car , drive to Sevlile and then train to Porto but no go) - Drive back to Madrid

I did wonder if it would be easier to rent a car in Granada, enjoy the area & then drop it off in Granada & taking the train to Madrid? (2.5 hours out of your way, but saves RT driving to & from Madrid.) Just an idea!

Hello
Thank you Sandancisco ! We now have reservation for the train Madrid /Granada and back. And since we are walking in Granada for two of the days we are there - what were we thinking ? ;) And Gail and stephengilbert thank you for your suggestions.
We are looking into staying in Pointe de Lima ,checking out Guimarães. and Braga. And we are checking into Maremma/Ucellina park in Tuscany that someone mentioned in this forum. WOW - Thank you all again for your input- It was difficult to choose from all the great ideas.
Wendy