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8 Nights in Portugal: Help needed!

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My gf and I (late 30's) will be in Portugal for 8 nights in late November. NYC to Lisbon & back.

We love food, wine, natural scenery (e.g. cork forests) and want to feel like we understand the place and culture without having to stop at every monument/cathedral. Prefer to mix in some nightlife too. We'll likely rent a car for the week, unless you suggest otherwise. We've been to several wine regions & wineries and do not *need* to visit the Douro, unless it's really unique.

1) Looks like we'll have to do 3 + 3 + 2 nights and choose to base ourselves in 3 locations; trying for 4 regions with 2 nights each too hectic? So, should we do Algarve or Porto/Douro for a couple of nights? Already planning on Lisbon + surroundings and Evota/Alentejo for 3 nights each.
2) If Algarve, which town is the best base for a couple of nights from where we can drive to east/west sides? I'm easily swayed by town with best food! :-)
3) In Alentejo, does it make sense to stay in Evora and do day trips to nearby Alentejo towns? Which are the not to miss towns?
4) Current plan: land in Lisbon at 8 am, rent car immediately and drive to Evora/other Alentejo town for 2-3 nights. Then spend 2 nights in Algarve. Finally, drive back up to Lisbon for last 3 nights.

5) Alternative is to try to pack in Coimbra and Obidos/Tomar for 2 nights and do 2 nights each in Alentejo, Algarve and Lisbon.

Appreciate any suggestions on how to best plan this. Thanks!!

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