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Portugal 2 weeks in July itinerary

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Trying to figure out if this itinerary will be too rushed/chaotic for a couple with a toddler.
Fly into Porto July 2014 2nd week and out of Lisbon 2 weeks later (15 full days):

Days 1& 2: Porto

Days 3 & 4: HIre car to drive out to Pinhao, Douro Valley - scenery, wine, local food.

Day 5: Drive to Coimbra and stay overnight at Palace hotel de Bucaco

Day 6: Visit Obidos in the morning, drive to Odeceixe

Days 7 & 8: Alentejo Region (Vila Nova Milfontes, beaches, etc.)

Days 9,10,11: Algarve - need to figure out where to stay as a good base to visit beaches like Praia da Marinha, Praia do Carvalho, Carvoeiro, Praia da Rocha, Praia Dona Ana

Days 12,13,14,15 - Lisbon - drop off car in and stay probably the Baixa/Chiado area. Visit Sintra as day trip by train.

Would love to hear suggestions on transport options and good places to base ourselves in the North and the South. Is it necessary to book all accommodation in advance?

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