3 week itinerary- what to cut

Usually people advise skipping the Algarve and I tend to agree. I’ve been there numerous times and I love it, but I go with my kids for an easy beach holiday. It’s very tourist focussed although not to the point that you can’t tell you’re in Portugal. If I was on a more cultural, sightseeing trip as you are I’d choose somewhere else. The coast just south of Lisbon is meant to be lovely. Sesimbra and Comporta are places I’d like to explore but haven’t yet. I have been to the Alentejo coast some years ago and would love to return. It’s stunning and very quiet.

I think it feels a bit choppy in the middle with your 1 night stays etc.
Without cutting much, I'd suggest a bit of a change
Porto 4 nights
Train to Coimbra 2 nights ( you don't need a car in Coimbra and train is direct) Pick up car at end of Coimbra
Stop in Obidos on way to Evora ( or1 night Coimbra and overnight in Obidos once the crowds die down,
Evora 2nights
I've never been to Monsarez, but it feels like an outlier
Lagos 3 nights
Sintra, drop your car 2 nights
train to Lisbon

Regarding the coastal drive Algarve to Lisbon, someone else can maybe comment, but it is a long drive compared to the main highway. I think we started it and found it long, but it is quite a number of years ago.

Thanks for the ideas and perspective on reworking this itinerary. Time to regroup! I'll repost when I have it figured out.

Revised itinerary incorporating some of your suggestions. This feels like a more relaxed trip and avoids the long hours in the car:

Porto- 5 nights (2 day trips)
Train to Coimbra- 2 nights
Train to Lisbon- pick up car
Evora - 2 nights (day trip for monoliths and Monsarat)
Beja- 2 nights ?- Moura, etc Trying not to do too much backtracking but interested in some of the fortress towns
Vila Nova de Milfontes /Alentejo coast - 1-2 nights (coastal hikes)
Lisbon (return car)- 7-8 nights (day trip Sintra gardens and trails, and maybe Cascais for coastal bike trail)

We're cutting the Algarve entirely in favor of the coastal area south of Lisbon.

Thanks for the many suggestions!

Drop the Lagos portion

Back in November we had a very similar itinerary. It sounds like you enjoy hiking and I would suggest cutting your time in Lisbon in half and taking the short 1.5 h flight to Funchal on Madeira for 3-4 nights….simply a wonderful place!! Also, we spent 3 nights in Evora and the mono/megalith day trip was wonderful, and a day trip to Elvis to see the border fort was well worth it. I think some folk on here don’t give Lagos enough credit for the wonderful coastal walks…even a day trip out to Cape St Vincent is fabulous; 3 nights there is sufficient though!! Enjoy your trip!

In my opinion, 7-8 nights in Lisbon is a lot! Lisbon is a lovely city, but not sure you can fill a whole week up there. We did 4 nights in Lisbon and 2 in Sintra, which I'm glad we did because doing everything we wanted to do in Sintra in one day would be a lot! Also agree in maybe flying to Madeira- that was honestly my favorite part of Portugal. I didn't make it to some of the towns you mentioned so I can't comment on those. good luck!

To your point, a week in Lisbon is more than we want but I was allowing extra days for day tripping. However, I like the Madeira idea a lot! Thank you!

We have stayed at the Pousada in Beja and loved it. Loved Monsaraz, Evora, and Coimbra. We felt Obidos was too touristy and crowded. Consider Tomar instead. We felt the Evora monoliths were definitely worth a visit. Use Ebora Megalithica for your tour guide. These people are passionate about presevation and education.