Feedback on 3 week (or so) itinerary, please

Day 1 (and possibly longer) will be lost to jet lag. Day 5 is a transit day, so you actually have 3 days in Lisbon and one of these will be spent in Cascais, so you are short changing Lisbon itself IMO.

The toll motorway between Lisbon and the Algarve is a rather dull drive - if you take the more interesting N120 road, it will be a full day’s drive including lunch and photo stops. If I had your timescale, I wouldn’t bother with the drive to the Algarve, (which is all about beaches and golf) and I would add another night to Lisbon, one to Evora and another 2 nights to your Obidos stop (more on that in a second).

If you do head to the Algarve, then stick to the western Algarve with only 4 nights there - the last time I drove Lagos- Tavira, it took 3.5 hours one way. Salema isn’t the quaint village it used to be - it’s doubled in size in the last decade, which has changed its character. Sagres and the Cape are windy and cold - take a jumper. It’s not the most interesting part of the Algarve. Aljezur Castle, the rock formations at Carrapateira and Monchique are worth visiting.

Obidos only needs a couple of hours and would not be my choice of an overnight base - I would stay in Caldas da Rainha, Tomar, Alcobaca or Batalha. Nazare (overrated) is ok if you want to see the big waves, but you are there at the wrong time of year for waves.

I haven’t been to Monsanto yet, so can’t comment on that.

Thinking about what Jennifer said (thanks), and chatting with my husband, we decided that ending our trip with some restful time on the beach sounded nice. We also thought it would be nice to add in a "road trip" segment (meaning reasonable drive times and one night stays from Pinhao to Evora), assuming that the drive would be mostly scenic on our Douro Valley > Monsanto > Marvao > Evora route. That would flip our schedule a bit. May I ask if this revised itinerary looks reasonable? I'm still mostly unsure whether overnight stays in Monsanto and Marvao add too much drive time and hassle to the trip. We would have 4 one night stays in a row, but also have a beautiful drive to lovely places and end up 'recovering' on a beach. Has anyone done something similar?

Fly ATL to LIS - pick up rental car after Lisbon stay
Days 1-5 - Lisbon (4 nights); enjoy Lisbon
Days 5-7 - Obidos (2 nights); visit Nazare, Batalha, Fatima, Alcobaca (overnight location may change)
Days 7-9 - Coimbra (2 nights); visit Tomar en route
Days 9-12 - Porto (3 nights); visit Aveiro en route
Days 12-13 - Guimaraes (1 night); visit Braga 'en route'
Days 13-14 - Pinhao (1 night); drive from Guimaraes to Peso da Regua then the N222 to Pinhao
Days 14-15 - Monsanto (1 night)
Days 15-16 - Marvao (1 night)
Days 16-18 - Evora (2 nights); visit Elvas en route; visit Evora and Monsaraz the next day
Days 18-22 - Lagos (4 nights)
Days 22-24 - Sintra (2 nights)
Fly LIS to ATL - drop off rental car at airport

I wouldn't recommend a car in Porto, Coimbra, or Sintra.
Instead of driving, you can use the train for a portion of your trip.

Train: Lisbon>Coimbra>Porto.

Day trips via train from Porto: Guimaraes, Braga, Aveiro.

Pickup car when leave Porto and visit the other locations before returning the car prior to your stay in Sintra.

And one more thing, I thought the beaches on the Silver Coast were nice. I haven't visited the Algarve, so I'm not able to compare, but perhaps spending more time on the Silver Coast versus driving to Lagos maybe an option.

Hello, My husband and I are planning similar itinerary in May 2022. I am still debating the route from Pinhao to Evora. Was it a nice drive from Pinhao > Monsato > Marvao > Evora? What places did you stay for the nights? Thank you.

We loved Sintra and stayed there three nights and made it our base to visit Lisboa (which we have visited before) - I easily could have stayed there 6-7 nights to visit all of the palaces. If you like hiking, the trail up to Pena and the Moorish palaces is a blast.

Obidos was sweet but kind of sad - it feels somewhat impoverished (there are lots of historical restrictions on what can be done to buildings inside the walls) - we stayed there for a couple of nights to recover from our jet lag and used it as a base to visit Alcobaca and Batalha but one night is sufficient if you are just visiting the city or you could stay further north by the water.

Regarding the car in Sintra: a taxi from the airport to Sintra will not break the bank, so it is quite easy to drop the car at the airport before heading to Sintra, where a car will be a hindrance indeed! And you'll save two days of car rental, which is a lot of money these days.