I've posted a couple of questions on this forum previously but now that I bought my airline tickets I know exactly how long and which days I will be there! I will be there in July. I've done my research and the places I want to go are finalized, now it's just a matter of putting all of the pieces together in the order that makes the most sense. A few specific questions:

1) Will Sintra be crazier on the weekend or on a Monday? I know it will be crowded regardless, but I'm trying to weigh if I should avoid Sintra on the weekend or on Monday when all of the guidebooks say to go to Sintra because museums and other sites in Lisbon will be closed.

2) The middle of the trip is where I'm having problems. Geographically it makes sense to go to Obidos, spend the night, and continue to to Coimbra. I like the idea of spending the night in Obidos to see the cute little town after the crowds have left. However, if it makes more sense for the itinerary, I could move it earlier in the trip and just do it as a day trip from Lisbon.

3) Going to Sintra to Obidos to Coimbra to Guimaraes to Braga is a ton of moving around. Ideally I've go from Coimbra to Porto and stay a few days in Porto before going to Guimaraes and Braga, but it looks like many of the sites in Braga are closed Sunday or Monday, so I need to push that up in order to make the most of my time in those towns. Any advice on how to improve this section?

4) Option 2 seems a little more doable; the trade-off is that I get only one full day in Lisbon before I start in on the day trips. I kind of like the idea of staying put and getting to know Lisbon for a couple of days.

Option 1
M Depart late afternoon
T Arrive Lisbon afternoon
W Lisbon
Th Lisbon
F Cascais
S : Lisbon
S Lisbon, Belem
M Sintra
T Sintra
W Obidos
Th Coimbra
F Guimaraes
S Braga
S Porto
M Porto
T Porto to Lisbon
W Depart Lisbon noon

Option 2
M Depart late afternoon
T Arrive Lisbon late afternoon
W Lisbon
Th Obidos (day trip)
F Cascais
S Lisbon
S Lisbon, Belem
M Sintra
T Sintra
W Lisbon to Coimbra to Porto
Th Porto
F Guimaraes
S Braga
S Porto
M Porto
T Porto to Lisbon
W Depart Lisbon noon

For those that have been to Portugal, how would you put this itinerary together with this number of days and these places?

How are you traveling - trains or car - makes a difference sometimes.

Both plans look good to me but for Guimares and Braga I would do those as day trips from Porto - relocating hotels takes so much time.

Trains go to all those places - check https://www.cp.pt/passageiros/en - can get discounts on inter-city trains but for short hauls like say trips to Sintra, Guimares, etc just buy at station day of travel.- www.seat61.com has loads of great advice booking own long-distance trains - general info trains www.ricksteves.com and BETS-European Rail Experts.

Obidos is a longish day trip and as you say the ancient walled town is best savored after daytrippers have gone. Or could do as a stop between Lisbon andn Coimbra same day.