Advice for Portugal itinerary and renting a car

The question is, do you really need to rent a car at all? You don't want/need one for Lisbon and Porto, obviously. You can take the train from Lisbon to Coimbra to Porto easily. I understand driving in Portugal is pretty easy outside of the cities; I have driven in Europe a few times but stuck to trains and buses in Portugal. I didn't feel the need to rent a car there, but if I were staying longer (my trip was about 10 days) and straying away from the big cities longer, perhaps I would have rented one for a few days. For a shorter stay, it seems like it would make less sense.

If you are going to be wine tasting, maybe it would be less stressful for not have a car at all? Take some kind of Douro Valley tour from Porto for one day and spend an extra night there.

You're giving Lisbon very little time, too. It's a huge city, and you have barely a day and half there. No plans to visit Sintra? (Not everyone wants/needs to, but it is a common day trip from Lisbon.)

I was there a couple months ago and went to all the places you've listed (except Beja) - and a few more since my trip was 23 days.

On driving . . . . GPS and a paper map are essential. I found out way too late that the TI's have a good (free) map of central Portugal. I had my Garmin and google maps on my phone, used both, sometimes to check one against the other. I didn't use Waze because it's a data hog. There are toll roads that you'll want to use. Pay the daily rental fee (about €2-3) for a toll reader. Actual driving times are usually considerably longer than the estimates, except when using the toll roads. Avoid driving in/out of Lisbon and Porto during rush hour. That can also slow you down a lot. In the Alentejo and Douro, roads are in good condition but they are mostly narrow with 2 lanes and there are lots of curves and hills. You don't need to go out to the airport to rent a car in Lisbon.

I stayed at Quinta de Marrocos in the Douro Valley and loved it, the price was good, the staff make you feel like family and the wines and dinners are great. There's a cork factory a few kms outside Evora, Corticarte Em Arte. You can book a "tour" on their FB page or by phone. You don't tour the factory, but they give an excellent presentation in one of their warehouses, explaining all about cork from acorn to wine corks.

It's a fast-paced itinerary, but you are hitting a lot of the highlights.

I’m a bit confused about you adding in the Alentejo when you list your likes as being anything on the water, art, etc. The Alentejo is far from the water and is more of an ancient ruins kind of area. With two nights in Lisbon, Alentejo, etc, that means one day in each of these places.

I would suggest dividing your time between Lisbon and Porto with a night in Coimbra on the way between the two. This negates the need for a car and will give you time to actually enjoy the areas you visit. Your current itinerary is pretty much all traveling from place to place without taking time to enjoy anything.

You are sensible to eliminate the Algarve, however 1/1.5 days in Lisbon isn’t enough and you are still trying to cover too much ground. I would allow 5 nights for Lisbon including at least one day trip to Cascais, Sintra or Evora.

Then either head to the Alentejo, where a car maybe beneficial if you want to visit the countryside then fly from Lisbon

OR

take the train to Porto for 2 nights and 2 nights in the Douro

OR

hire a car in Lisbon and have 2 nights somewhere near Caldas da Rainha to explore Tomar, Santarem, Obidos and some of the traditional towns in this area before heading to Porto for 2 nights.

I haven’t been to Beja. Some friends recommended it and other friends said it was just a regular place, so why go there?

The dull toll roads in Portugal are easy to drive as the locals don’t use them! Some of the driving on the smaller roads in Portugal is of a questionable standard.

You have too much planned for your 9 days. Lisbon deserves minimum of 3 days, more if you do day trips to Sintra and Evora.

Madrid deserved 4 day minimum, also day trips to Toledo (MUST) and Segovia.

If you rent a car and one country and drop it in another, you are likely to incur a huge drop charge.

2 nights in Porto is fine, but if you explore the Douro River valley you need more time.