I’ve decided on Portugal; guidance, please …

I see you are from Paso Robles. Do you enjoy wine? We have visited wine regions all over Europe and the U.S. We spent 2 nights on the Douro River and would have enjoyed more time. The river lined with steep terraces planted with grapes is gorgeous. I don't really care for port, but my husband does and we discovered that the wineries typically have more than just port. I think we only did one actual, formal tour and tasting and that was where we stayed. Other than that we sought out pictuesque wineries to enjoy a glass, or share a glass of wine.

One city you might consider is Batalha. It has a lovely monastery and is close enough to the coast and Tomar. Batalha doesn't have a lot of sites or restaurants, but it was very convenient for visiting the other areas.

If you are talking May/June 2025, I'd come up with an itinerary soon and start booking hotels. Portugal is extremely busy, especially in your time frame.

Thank you. Yes, my wife and I are both actually work at a winery in Paso Robles. She especially enjoys regular wines and I do enjoy port. We don’t want the weathers to be too chilly, So I am trying to push our travels as late as possible In an effort to avoid major crowds. Do you think it would make sense to rent a car in Lisbon and drop it off in Porto, and fly back from there? Or itinerary idea that could circle from Lisbon to Porto and then back into Lisbon that would make sense?

Can go north of Porto (Minho region) since willing to rent a car. Ponte de Lima is a small town with a nice River to walk along. Viana do Castelo is on the water too. Either could be bases for day trips in the area.

We've been twice to Portugal, both times in April and it was very pleasant weather wise. With the dates you have chosen I would personally go for October, based on what the average temperatures are. My son was there in June and it was terribly hot that year. That many days gives you a good chance to enjoy everything.

A sample itinerary with some of what we have done:
Lisbon 4-5 nights ( get over jet lag, day trip to Belem and Caiscais) ( You might want to also look at Caiscais as a spot to stay)
Sintra 2 nights ( Sintra is very touristy, but staying over helps)- pick up car in Sintra
Drive to Algarve - stay in Lagos 2 nights, Tavira 2 nights ( or just one of them for longer)
Drive to Evora 3 nights
Drive to Coimbra 3 nights- daytrip to sites near there.- drop car
Porto last 3-4 nights.

Or you can skip Algarve altogether and dedicate that to the north more with time in Douro, or sites north like Guimares. I suspect they may be less touristy than Lisbon area and Porto.

In terms of food, lots of great choices. I loved both the duck, and the "black" pork ( can't remember why it was called that.

Lynn mentioned Minho. We went to Braga and Guimaraes in Minho and found both cities beautiful and fascination. They are about an hour apart by car is my recollection. Guimaraes is considered to be the "birthplace of Portugal". Unless you want to be on a beach, I would skip Algarve. Minho has beaches as well. We did a daytrip to pretty Viana do Castelo to see Santuario de Santa Luzia. It's a pretty church with a lovely view of the city. I believe there were beaches in that area, as well.

From the Douro River area, a reasonable daytrip would be to the gorgeous, Santuário de Nossa Senhora dos Remédios. Google it, for many pictures! A similar church is Bom Jesus do Monte.

Oh, I'm sorry, I missed your follow up question. We rented a car just outside Lisbon (Sintra) and dropped it off in Braga. We had intended to take the train from Braga to Porto, but there was a strike, so we took a bus which worked out fine. It was nice to have a car to explore the Douro River area and Minho.

Maestro

Portugal is a long skinny country. In order to do a loop from Lisbon you have to go one way, double back past Lisbon, go the other way and then double back to return to Lisbon.

You may wish to consider open-jaw. We only had 2 weeks and did not want to retrace our steps. So, we chose to fly open-jaw into Porto and home out of Faro. It would have cost about the same if we reversed the open-jaw.

I would note that your trip is considerably longer than ours so you would have more time to do the loop and to stop at different cities as you go back and forth over the same area. Flying return in and out of the same city will save you some money.

Picking up and dropping off your car from the same city will also save you the one-way drop off fee. However, doing the big loop will result in doubling your fuel costs and toll charges. Good luck.

We did a loop. Might have been more of an oval but we explored some of the more eastern areas including the Schist villages. We went to Piodao and explored Serra da Estrela Nature Park, before making our way to the Douro River. That said, for Portugal, if you are interested in Lisbon, Porto and other cities more in the west, open jaw can make sense depending on your home airport. It wouldn't have worked for us at a reasonable cost.