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Please help with itinerary for first timers to Portugal

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Hi Fodorites!

My husband and I are planning our first trip to Portugal next May, and would love your help. We are trying to keep it to 9 or 10 nights, but of course, find so much we want to see that it’s hard to make choices. We are early 60’s and love great food, wine, scenery, history, local charm, museums and hikes.

Prefer to limit one-night stays as much as possible.

Here is our tentative itinerary. We are thinking of flying into Lisbon and out of Porto (or vice versa).

Fly to Lisbon. Stay 3 or 4 nights with day trip to Sintra
Rent a car and drive to Obidos, lunch, and then overnight in Coimbra 1 night.
Drive to Douro Valley—2 nights
Drive to Porto, drop off car. Stay 3 nights with day trip to Guimares and/or Braga/Bom
Jesus
Fly home

If we reverse trip, we would stop/lunch in Coimbra and overnight in Obidos.

Questions for those who have been there:

Lisbon or Porto first? We’re thinking Lisbon as we like to do bigger cities first while fresh.
Which also asks…overnight in Obidos or Coimbra?
Three or 4 nights in Lisbon?
Are we missing anything we will be sorry for later?
Should we avoid Coimbra during Quimas das Fitas?

Haven’t gotten to hotels/inns/pousadas yet, but would love advice there, too. Charm and sense of place more important than price, but prefer to average under 200 euro a night. One two splurges ok.

Thank you all!
Hax

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