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Planning for Portugal, 15 days in April/May

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DH and I are planning a trip to Portugal for late April/early May. We've got 15 nights and only a rough sketch so far. I liked Tedgale's TR from last year and I'm generally following his plan (thanks Ted, so helpful!). We are in our mid-50's. DH is a geologist, I'm a painter, we travel often and really love great views, museums, lively urban areas, stunning landscapes. My favorite travel moment is usually a glass of wine with a great view of the sunset. Or of crowds of people. I'm thinking of this:

Pick up a rental car at the Lisbon airport, return it in Porto.
3 to 4 nights in the Alentejo region
1 night near Tomar to see the several UNESCO World Heritage sites in the area
2 nights Douro Valley? (not totally sure about this but the landscape looks exciting to me)
3-4 nights in Porto (visit Guimaraes)
5 nights in Lisbon

We have been to Italy often and really love the off-the-beaten track hillside villages. We prefer to avoid seriously touristed areas as we never really enjoy that. I've used the website 'the most beautiful villages of Italy' to find villages to visit. Are there beautiful villages in Portugal we should visit and even stay in?

Where should we stay in the Alentejo region? Should we base ourselves somewhere or would we need more than one stay (and that's fine by us) to really see it? Would it be worth it to adjust our schedule to spend a day or two hiking along the coast on the Rota Vicentina? Should we head to Monsarez? Or other villages?

Thanks in advance for your help ~ Rose

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