Considering a 11-12 day trip to Portugal ( first time) in late October. Lisbon and Porto are clearly on the list, with side trips to Evora and Sintra. We like to be in nature, to hike or walk, and we like good food and wine for dinner. One friend said we should definitely go to Madeira. Would love to hear from Fodorites what your favorites are. We like water, but obviously aren't coming to sit on the beach. We are seniors, but are quite active, and we are fine with driving ourselves. Thanks in advance for any suggestions: places to visit or hike, restaurants to enjoy, etc.

We were in the north in (early) October some years ago and the weather was starting to turn wet. In late October I'd imagine it will be more of an issue.

By far our favorite part of the country then was the Alentejo, of which Evora is, I suppose, the capital. The weather was pleasant, the vistas superb, the villages picturesque, and the food was very good. We stayed a few nights at a country hotel near the hill village of Monsaraz, and it remains to this day one of the nicest places I've stayed in all of Europe. HORTA DA MOURA - HOTEL, ALENTEJO, ALQUEVA

We have been to Portugal 7 times, most recently, a year ago in March. We flew into Faro from the UK and stayed in the mountains in Monchique. We drove to the beaches and the lighthouse, loved it all. We drove to Lisbon and left the car. You won't need a car in and around Lisbon, public transport is great. Visit to Sintra on the train easy.

We visited Portugal in September 2018 - flew into Porto and obtained a rental car from Auto Europe. Drove to the Delfim Douro Hotel so that we could explore the valley and the wineries. You can view our trip details at WWW dot JUSTTRAVELINGTHRU dot COM / portuga_visit.php

I would suggest that you not limit yourself to Lisbon and northern Portugal, the Algarve geography is amazing and the cities there are smaller and the seafood is fantastic.

Have fun.

Since you seem to be into walking and hiking the IIha deserta would be a good place to unwind and take a leisurely stroll. For hiking, I would suggest you check the Fisherman's trail, It's unique and appealing.
Also, there is this natural park along the coastline, very beautiful, but the name is a mouthful so I can't really remember it. It is good for walking too as well as soaking in the view.
Asides these, I am really fascinated by caves and rock formations, so if it interests you check out the Lagos elefante cave or the cave of benagil.
Last, If you are up to it, then Azores waterfall would definitely be a go though it's quite a hassle to get there
Hope you find this helpful
Have fun!

I have just tried many times to book this hotel on line, but am unable. Do you remember how you did it?
Did you have to call the hotel directly?
Thanks.