Help with 10 day Portugal Itinerary

I assume you've already booked the airline ticket into/out of Lisbon? Otherwise, it is often easier to fly "open jaw" - into Lisbon out of Porto on one "multi-city" ticket. Sometimes it is not more expensive to do it that way - sometimes it is actually cheaper than a round trip ticket. (All depends.)

Anyway - if you've already booked that ticket more than 24 hours ago (less than 24 hours and you have free cancellation), my personal preference would be to hop in a train north to Porto as soon as you land in Lisbon. And put all of your days in Lisbon at the end, so you don't split them up. This is just a personal preference of mine after many trips - but some experienced travelers don't mind splitting up your time in one city.

You have eleven nights. (I like to plan by nights: where are you sleeping?) I just spent nine nights in Portugal in May. I did this:

Lisbon (4 nights)
Coimbra (2 nights)
Porto (3 nights)

I did day trips from Lisbon to Sintra and to Cascais on separate days. On the train north to Coimbra, I stopped for a few hours in Tomar (lovely little town). And from Coimbra, I took a quick day trip by bus to Nazare (which I really loved and regretted not spending a night there).

Porto was probably my biggest disappointment, in part because it's gotten very touristy, plus it rained the last two days, and I had planned a day trip to the Douro Valley for one of them, and there just isn't a lot to do in Porto proper on a rainy day if you don't drink (I don't). Otherwise, it's certainly worth a visit, but two nights would have been plenty for me.

Coimbra is not touristy at all, but it's also not very big. It's a lovely old university town; you can tour the university at the top of the hill. But it doesn't take much time to see. You could do this a day stop off the train if you wanted to (finding a place to store bags for a few hours might not be simple but probably doable - no bag storage at the train station). Otherwise, a night is probably a decent amount of time in Coimbra for a quick visit. If you like Roman ruins, add a night and see the ones just outside of town (I didn't).

If I were doing it over again, I'd probably do four nights in Lisbon, take the bus north to Nazare for two nights (maybe day trip to Obidos, which I missed but hear it is very crowded with tourists anyway), bus to Coimbra for two nights, day trip to Tomar by train, and then train to Porto for two nights. Many people seem like staying over in Sintra as well even though it is an easy day trip by train from Lisbon. But, Sintra is really super touristy in the daytime and it seems like it would be much quieter at night. I can see enjoying a night or two in Sintra if you have the time.

In your case, you'll probably have to spend the final night in Lisbon if you don't want to head north immediately like I suggest. So you'd have ten other days to play with. I think 4-5 nights in Lisbon is good unless you decide to spend nights separately in Sintra or Cascais. 3 nights in Porto would be fine if you find day trips from there you'd like to do.

Thank you. Great information! Put together a bit of an itinerary. Anyone have thoughts this?

Tuesday
Arrive in Lisbon in AM, pick up rental car, drive to Porto.Spend the evening in Porto

Wednesday - Thursday
Porto (add side trip Thursday if we’re bored)

Friday
Side trip to Aveiro, Costa Nova, add Buçaco Forest if we have time
Sleep in Porto

Saturday:
Leave Porto in AM
Drive to Nazare, spend day there
Drive to Obidos, sleep there

Sunday
Spend 2-4 hours in Obidos in AM, if we didn’t have enough time in Obidos previous night
Drive to Cascais, spend day, sleep there

Monday
Drive from Cascais to Sintra, spend day there
Leave to Lisbon that night, drop off rental car, sleep there

Tuesday-Friday
Lisbon (add Evora 1 day if we want)

Saturday
Leave

I didn't drive in Portugal. I understand it's pretty easy (I've found it easy enough in some other European countries) but I understand driving in Porto or Lisbon isn't fun for tourists - may be very stressful. (Also Sintra may not be fun to drive in these days because of the new pedestrian-only zones in town. A friend of mine recently spent (she claimed) a few hours circling around trying to find her hotel because of the confusion there - and she has driven in Europe a few times.) Plus, personally I wouldn't want to drive jet lagged after a long overseas flight. So I suggest you take the train right to Porto and pick up the car as you leave Porto.

If you haven't been to Europe before, you may not be aware of how much better their train system is than say Amtrak. I actually love trains and look forward to train trips in Europe. You really wouldn't need a car at all in Portugal, but it could make sense for part of the time.

I will echo Andrew’s comments about the car. There is no reason to drive from Lisbon to Porto - especially after flying here from the States. The train station (Oriente) is just a few stops on the metro from the airport and is cheap, easy and comfortable. Book tickets 2-3 weeks ahead and save 40%.
If you want, you could visit Aveiro as a day trip from Porto or on your way back south as it’s right on the train line.
I’m not crazy about either Nazare or Obidos and much prefer Coimbra to either of them. Obidos is worth a couple of hours only, IMO.
Also, what he said about Sintra is very accurate. It’s much better to train from Lisbon to Sintra than driving or busing from Cascais. The bus from Cascais is crowded and makes way too many stops. And, driving in Sintra is problematic right now for the people who live there - not to mention for tourists. My last trip was pretty awful from Cascais. Taking a small group tour from Lisbon would be my recommendation as someone else does the driving. Or get a private driver.
I would suggest no more than three overnight cities, Lisbon, Porto and maybe Coimbra. Evora is a worthwhile day trip from Lisbon.

Thanks for the feedback, very helpful. We re-worked our itinerary a bit, taking that into account.

We ditched the idea of a rental car. Sounds like we'd only be able to use it after leaving Porto and before getting into Lisbon, and not in Cascais or Sintra, so it's pretty pointless.
We left out Nazare/Obidos, even though we really wanted to see them, in order to see Coimbra. We don't know how to choose between Aveiro and Nazare options since we've obviously never been there to know, so we just made our best guess.

Tuesday
Arrive in Lisbon in AM, train to Porto. Spend the evening in Porto

Wednesday - Thursday
Porto (add side trip Thursday if we’re bored)

Friday
Train to Aveiro, bus or taxi to Costa Nova
Sleep there *We don't want to travel back to Porto, only have to repeat that travel again the next day+ in order to get to Coimbra

Saturday:
Train to Coimbra
Day there
Sleep there *We don't want to train 3+ hours to Lisbon at the end of a long day

Sunday
Train to Lisbon, spend day in Lisbon

Monday
Day trip Sintra from Lisbon

Tuesday
Day trip Cascais from Lisbon

Wednesday-Friday
Lisbon (add Evora 1 day if we want)

Saturday
Leave

Thoughts?

If you want to add a night in Nazare, you could take a direct bus from Coimbra to Nazare, then another direct bus from Nazare on to Lisbon.

The only slight modifcation i would suggest is the day you go to Sintra. Monday is the day a lot of museums in Lisbon are closed. Therefore, Sintra will be even more crowded on Monday. I would suggest going another of your days in Lisbon.

Given your stated interests, the itinerary you mention will work. My personal preference would be to split your visit between Porto and Lisbon, with more nights in Lisbon. The other cities you mention are all worth visiting, but if you want to experience local culture, I recommend spending less time moving between hotels.

Lisbon is getting more touristy every year, and if you are just there for a few days, you will tend to see only the most touristy places. The area around the new cruise ship dock is in danger of being loved to death. If you are in Lisbon longer, you will have time to get away from that reality and get into the neighborhoods that still have mom and pop restaurants. You will also have time to visit weekly public markets, take in a fado show, and maybe even visit the same coffee shop more than once.

In Lisbon visit the Alfama region and find out which bar or cafe has a fado show. I am a great fan of Airbnb for places to stay though they weren't available when we were last in Portugal. I would recommend Obidos, Nazare, Evora, Alcobaca as interesting towns to visit. You might find it easier to travel to these small towns by rental car. Sounds like you will have a great time there!