We spent 14 nights in May visiting Portugal and got a lot of good information from the forum before our trip. Weather was cool and very hot at different points so needed the varied clothes I brought but we were very lucky with the weather during our whole trip.
Carvoeiro
Accommodation: O Castelo Guest House with a huge terrace overlooking the beach/water. The staff were amazing and it was a good place to get over jet lag and gorgeous cliffs/scenery everywhere.
We had a rental car so want to let others know that there were many ‘white knuckle’ moments as the roads are often narrow and difficult (husband called them 'goat paths'). On the road to find viewpoint Algar de Albandeira, avoiding a truck we hit a pothole and popped a tire. A local stopped to help and let us know we weren’t the first and we were lucky that our spare tire was in good shape, and O Castelo found a tire shop so we got that taken care of in good time. We still loved our time in Carvoeiro. For restaurants, Café Fino was good for breakfast, and A Gale was excellent for dinner (monkfish/prawn skewer and Cod Portuguese style). We also took a boat tour of the coast from Carvoeiro Caves which was a beautiful way to spend a morning. After 3 nights, drove to Lisbon and dropped off the rental car.
Lisbon
Accommodation: Hotel Lisboa Pessoa. We really enjoy places with either private or general balconies/rooftop terraces for morning coffee/evening wine, and with costs rising in Lisbon we chose this hotel in Chiado from another I’d bookmarked. Large room and quiet for being as central in Chiado as it is.
We did an Eating Europe food tour through Mouraria, and Portugal Me and You Tour in Belem that included skip the line to the Jeronimos Monastery and skip the line to get a Pastel de Belem (well worth the money) and both recommended. One day we did 2 Rick Steves’ walks – Baixa and Barrio Alto/Chiado, and another day we did the Castle and Alfama. We love castles and spent longer there than most people might, but enjoyed walking the walls and the grounds. We made a small detour in Alfama that I only saw briefly mentioned in the guidebook that I recommend – Sao Vincente de Fora Monastery. The altar was being renovated, but there was a lot to see here, and the view from the rooftop was spectacular. I want to give a shout out to a restaurant recommendation by Suki – Pinoquio. The prices were higher than other places we ate in Lisbon, but the portions were huge – the delicious monkfish/shrimp and rice easily would have been enough for both of us. So the prices ended up not really being that much more. After 4 nights, picked up new rental car to drive to the Douro Valley.
Douro Valley
Accommodation: Casa Do Visconde De Chanceleiros. Huge room and gorgeous spaces with gardens and views on every corner. Absolutely lovely staff and fun English Bulldogs!
Driving in the area was scary – I stopped looking out the car window and focused on my phone while my husband drove up and down the roads. We loved this part of our visit though. They recommended a Douro boat tour with Magnifico Douro and it was a beautiful morning. We chose to eat dinner at the guesthouse each evening so as not to drive that road more often than needed, and all 3 meals were tasty and several courses with the best views over the gardens and valley. After 3 nights drove to Porto for our last 4 nights and dropped off rental car.
I've run out of space so will add our time in Porto below.