We are 2 middle aged couples on a first trip to Portugal in October-November. We'll have a car, flying in and out of Lisbon. We would like to select 3-4 bases from which to explore, then wind up in Lisbon 3-4 days. We know we know we want to explore the W. coast, Porto and the Douro Valley, and Evora, probably skip the Algarve. Any suggestions for good places to stay from which to explore? We are interested in food and wine, smaller towns, history, local arts and crafts. We have 16 days.
Lisbon can easily fill 5 days or longer if you want day trips to Cascais or Sintra. Porto itself can be seen in a day, but it’s half a day to get there from Lisbon.
Allow at least a couple of days for the Douro - the beautiful town of Lamego is a good base - climb the old steps to the Shrine of Nossa Senhora dos Remedios for fantastic views.
A good base for seeing the pretty towns of Tomar, Santarem, Obidos and Alcobaca is Caldas da Rainha, a spa town which has a good local market, plenty of museums and cafes and is renowned for its painted tiles. You could easily spend a week here.
Evora is best with 2 days there ie one night.
I'm planning a 22 night trip, starting in (yikes) 3 weeks. Evora seems like a good base to explore the Alentejo, (Elvas, Monsaraz. For the Douro Valley, I'll be in Peso da Regua. Vila Real was another option. I'm planning to stay in Porto after I drop the car. I'm doing a string of 1- and 2-nighters with the car. The hardest part of planning for me was/is choosing among the many enticing options - especially between Porto and Lisbon. I've decided on 3 nights in Tomar as a base. I'll let you know how that goes in mid-June after I get back.
I'd suggest starting in Lisbon, with a day trip to Sintra. Then after you're over the jetlag, pick up the car and return it at the airport. I'm using the DK Eyewitness and Lonely Planet Portugal guides. I also have a 5-year old Michelin guide from a friend.
The Algarve is mainly for beach people. My view is why pay all that money to fly to Europe and go to the beach, when the beaches in the Caribbean are generally much better.
I would use Lisbon as a base for Evora and Sintra, then spend a couple of days in route to Porto (visit Obidon, Navarre and Batilha Cathedral). From Porto, you can take a Douro Vally river cruise, also a day trip to Santiago de Compostela in Spain. The Douro Valley is amazing. If you don't take a cruise, take the train up the river, the rail tracks run right on the north side of the river.
Either Caldas da Rainha as mentioned by Jennifer or Tomar as mentioned by Chani would be a good base for visiting Alcobaca, Batalha and the Convent of Christ. We stayed one night in each. There are also caves in the area (we didn't visit) and a quarry full of dinosaur tracks in Ourem which we found interesting.