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Portugal general safety advice and comments on itinerary

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We are three families with pre-teen kids traveling to Portugal in late Aug. The ladies/kids are traveling to the Azores for 5 days and then meeting the men in Lisbon who don't want to or are unable to take the full 2 weeks off. We will be limited to 11days in Portugal. The most convenient airport for us from the States is Lisbon and the Duoro valley and Algarve is a must which means there is quite a bit of driving involved. We have broken down are days as follows

8/18, 8/19 - Lisbon including Sintra/Cabo Da Roca. This of course is very tight but most folks would rather skip a big city and allocate more time to other places in Portugal
8/20 - Drive to Obidos (52 miles from Lisbon), From there cover Batalha and Tomar (pick the latter if running late). Drive to Coimbra (one hour from Tomar) and overnight in Coimbra
8/21, 8/22 - Duoro valley. Take IP3/A25/A24 up to Peso da Regua. Enjoy the scenery and overight in Pinhao. Visit wineries, consider the train from Pinhao to Pochinho
8/23 - Leave Duoro valley and head to Alentejo region. Long day of driving. Take a lunch break at Belmonte (2 hours from Pinhao) and overnight in Marvao (2 hours from Belmonte. Be prepared for narrow steep roads in town)
8/24. Explore Marvoa in the AM and leave for Evora (2 hours). Overnight Evora
8/25 Explore Evora AM and leave for Algarve about 2.5 hours.
8/26, 8/27 Hotel in Lagos. Must in this region is visit to Ponte da piedade, boat trip around the caves, Sagres peninsula, travel along to Aljezur and visit Silves if possible
8/28 Overnight Lisbon, return car
8/29 Fly out
As stated earlier we realize this is an aggressive itinerary but the guys refuse to take more time off and accept the fact that there will be quite a bit of traveling around involved. Having said that, is it doable?
Second qns: a few times we will be visiting small towns during the day and our luggage will be in the trunk. Is that safe? I have read about car break ins in some coastal towns near Lisbon but not in the above mentioned towns (Obidos, Tomar, Belmonte, Evora). Should we worry?
Lastly, how are the roads between the Duoro valley south towards Belmonte and Marvao? Am I underestimating the driving time?
One more: Are there any must see places not on this list? What would you cut/add...
Any/all feedback is greatly appreciated. Thank you.

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