Mid October in Portugal

Ten days is a good length of time to cover Lisbon to Porto and a car is useful so you can visit some of the places that aren’t reachable by train such as Tomar, Obidos, Alcobaca, Aveiro and Coimbra. If you just want to see Lisbon and Porto, then just take the train. Cascais and Evora are possible day trips from Lisbon. See the Douro from Porto.

There isn’t a rail service between Lisbon and Madrid, so you would have to fly or take a bus. Madrid deserves 3-4 full days, so would be best left for another trip.

I would stick with Portugal and the train - there will be plenty to do (and remember that you probably won't be at 100% the first day - or two- due to jet lag anyway). Ten days isn't really worth to try to combine with Spain, save it for a separate visit. The connections between Portugal and Spain are not as good as one might assume.

Rent a car when leaving Lisbon. Visit Evora, Coimbra, Guimares, Porto and more.

Lots to see in Porto. The train is under 3 hours. We took a Viator tour of the Douro Valley with wine tasting. Loved it!

If Madrid is a "must see" on this visit - it's an hour flight from Lisbon - quite inexpensive ($45 on TAP in October 2019) - and the Lisbon airport is closer to downtown than in any major European city I've visited. Sadly - that's not the case with the Madrid airport - but Madrid is very worth it. Then again, so is Sevilla - and it's close by to your Portuguese plans as long as you have a car.

You likely need to decide if you want to visit Spain or Portugal. With only ten days, doing both will short change you on both places. While seeing a number of the smaller towns in central Portugal is quite nice, with ten days, I would stick with Lisbon and Porto - with maybe a one night stopover in Coimbra. The train is so easy and cheap and there are many day trips (via train) from both big cities.

With the exception of Alcobaca, every city/town mentioned in this thread has rail service, though I assume the Douro valley would be best by car or bus tour. This is a relatively short trip, and apparently a first trip to Portugal. How many days are you going to have left after you see the best of Lisbon/Sintra/Cascais, Coimbra and Porto? I'd plan to use the trains where possible and limit my car rental to just those days when I wanted to (and had time to) spend time in smaller towns--which might even be zero days. A car in a place like Lisbon is an expensive annoyance.

I wouldn't recommend splitting this trip between Spain and Portugal unless the overwhelming interest of the travelers was art museums. In that case, there might be some justification for going to Madrid. Otherwise, there'd be too much transportation time spent moving back and forth. (I'm assuming you already have round-trip flights into and out of Lisbon, correct?)

There is so much to see in Portugal that painful decisions will have to be made to fit the time available. As for Spain, it's a multiple-month proposition even for rapid travelers.

Thank you all. It looks like we should plan on 12 days and all in Portugal. We will fly ORD to Lisbon. Sounds like we can do a nice trip via train. I like driving but it’s over $1000 for a small car + gas etc. So that in mind what would you recommend? I think we need 4 days in Lisbon fly in and out days. 2 in Porto leaving six days to see???

I would add at least one day to Lisbon is you want to do day trips to Sintra, Cascais and one more if you want to do Evora. You can easily spend a day seeing the sights in Belem. And, if you want to see the Douro, add at least another night to Porto. An afternoon spent at the Port lodges across the river is a very fun thing to do, as is a lunch in Matosinhos.

A day trip to the Douro is very nice and there are numerous tour companies that do a fun day, albeit a long one. Add one more day and make a day trip to Guimaraes or Braga from Porto.

Two nights in Coimbra would give you a full day to do a tour and enjoy the excellent food. Go Walks does a great walking tour that includes the university and library.

One thing I enjoy most about Portugal is the more relaxed pace. If you can force yourself to slow down a bit, you will have more of a sense of Portugal.

We are wrapping up our week in Lisbon and are off to Evora tomorrow morning. I can tell you that even with a week, we are still leaving with hopes of returning to see what we missed. If you're a museum buff, there are easily a couple days' worth of them here. Take time to enjoy wandering through the neighborhoods. Eat. Spend a day in Belem and one in Sintra, and you've filled a week. My point here is don't spread yourself too thin. Prioritize your wishlist, and with only 10 days, stick to Lisbon and Porto by train.

There's very little you can't visit by train. I loved the monasteries of Alcobaca and Batlalha which you can see with a guided tour from Lisbon. Coimbra is on the main train line between Porto and Lisbon. Aveiro is an easy day trip by train from Porto. Stick with the train and you'll still find you won't be able to see everything you want in 12 days.

You can fly non-stop between ORD and Madrid / Lisbon and back. You can also fly non-stop between Barcelona and Lisbon for less than $50.
If going to Madrid, make Madrid your home base and sleep there for four nights and visit the Royal Palace and Picasso’s Guernica at Centro de Arte Reina Sofia. Another day visit the Prado Museum.
I was in Madrid on a Sat night and could not get over how loud the city was. To appreciate it more, enjoy an early evening stroll along the pedestrian streets as you pass families with their strollers and young people having fun. To learn more, buy Rick Steves Spain guidebook. You can download an electronic version from his app.
From Madrid, take a direct train to Toledo for the day (45-minutes). You’ll need to hop on the bus to get dropped off in the old town, just follow the crowd.
Another day trip option from Madrid is Segovia that’s a 2h direct train ride away.
From Madrid take a direct train to Barcelona (3h 15m). You’ll need to buy your ticket before leaving home because reservations are compulsory and this train sells out quickly.
In Barcelona take Rick Steves self-guided walks and also visit the Picasso Museum and Sagrada Familia. Buy the ticket for the church before leaving home. Touring the cathedral is enough so no need to take the elevator to the top. I would sleep in Barcelona for three nights.
In Lisbon take Rick Steves self-guided walking tours of the old towns which means you’ll need to buy his PT guidebook. You should also take day-trips to Sintra and Évora by train. I would sleep in Lisbon for four nights.