After having successfully traveled internationally to Croatia and Italy, I'm thinking about Portugal for the spring and planning about 4 weeks from the beginning of May to early June 2022. I haven't bitten the bullet to get the tickets yet, as I'm still toying with the itinerary. We are upper 60s, mid-70s now (how did that happen?!) and definitely like to go at a slower pace than we once did, especially since we have more time. We will get a car for part of the trip. We prefer staying in places @ 3 nights, if it makes sense, though there will be times where it makes sense to stay less.

When we do day trips, we like to keep it low-keyed and visit maybe 1 or 2 places, but we don't need to visit every small town. We enjoy leisurely walking around the town we're staying in and don't have to see all the sights.
We love art/history/walking, and of course, views and vistas. We enjoy good food but we're not foodies so small and local and less fancy is better than Michelin, though we wouldn't say no to a very special restaurant.

Very tentatively, here's what I'm thinking:
Arrive Portugal and go directly to Sintra at the beginning:

Sintra (3)
Lisbon (5/6)
Lagos/Algarve (3/4)-- I'm not sure about this stop. It looks beautiful but it is a long drive. I'm open to pros and cons of visiting this region.
Evora/Alentejo (3) - at least one day trip from the town to explore region
Obidos or Tomar (2/3) -- Which one should we stay in? I've read that Obidos is too touristy, but a lot of folks love it. Tomar had intrigued me and, in a trip I planned for 2020, I had included Tomar and would be happy to do that again if you think it better staying there than Obidos.
Coimbra (3) - Very interested in seeing the Roman ruins at Conimbriga as well as the city itself.
Douro (2) - We don't drink much, though I will definitely imbibe some (!), and the vistas look lovely. It seems worthwhile to stay in one of the quintas.
Guimaraes - (3) - Includes a day trip to Braga
Porto - (3/4)

So what do you think? What are your opinions, recommendations, suggestions? Even with 4 weeks, it feels like there's one too many stops, though all locations appeal. If we go to the Algarve, I'd consider consolidating the Obidos/Tomar stop with Coimbra but just not sure. Both regions sound great.

Anything that is a must that I'm missing? Anything I shouldn't bother with? We are city folks and enjoy the life of cities, but if there is a wonderful non-urban place you think would fit in, I'm also open to suggestions!

Thanks - it's fun planning again!!

Hi progol
I remember your planning your trip and am glad that you'll be able to visit next May.
I like your itinerary, starting in Sintra for 3 nights to be able to see all the sights properly and without the rush, then moving to Lisbon. We have 6 nights coming up in Lisbon next month, which won't be too many for us as we're also slower travelers now. About the Algarve--we spent 6 nights there in November: 3. outside of Lagos and 3 in Tavira.

Maribel,

Thank you! I’m excited to finally be planning Portugal again! And, fingers crossed, this time it will happen.

It does sound like the Algarve might be worth visiting then - from photos I’ve seen, it does look beautiful. I’m still mulling this over but I’ll try to keep it in.

What do you think would be better for 2-3 days - Obidos or Tomar? I had the latter in my earlier plan and still lean toward it, but I’ve been reading lately how much people like Obidos, possibly because of reduced numbers due to covid?

When we were in Obidos, the side streets were empty of tourists and some of the hotels looked really nice. It might be like the Mont Saint Michel or Bruges, evenings will be devoid of the crowds.

https://flic.kr/p/2gwPU9d

We were in Obidos in June a few years ago and it was crowded all the time, and parking was difficult to find. Staying in the lovely castle Pousada made our time there tolerable. It is a pretty town but sadly given over to tourism. We didn’t visit Tomar. We used Obidos as a base for exploring Alcobaça( don’t miss), Batalha, and Nazare.
I like that you are giving Guimares several days which it deserves. The Minho region where Guimares is located ended up being our favorite area of Portugal. We traveled into Galicia, Spain from there.

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Hi progol,
I remember your initial planing of your Portugal trip and am so glad that you'll be Portugal bound finally next May. Â I like your plan to spend 3 nights first in Sintra to take in all the sights slowly and then move on to Lisbon. Â We have 6 Lisbon nights coming up next month, which suits us well, as we've become much slower travelers. Â The sights of Belém can take up a whole day for us.. Â
About the Algarve: Â we did spend 6 nights there in November: Â 3 outside of Lagos and 3 outside of Tavira after 2 nights spent on the Alentejo coast (wonderful cliff walking on the beautiful beaches there), but the Algarve is not our favorite region in Portugal. We visited because we hadn't been there in many years but left underwhelmed (didn't golf or do water sports, which are the 2 main attractions). Â I had anticipated not being enchanted by it on reading Isabel's excellent trip report. Â We did enjoy the western coast scenery, especially the Costa Vicentina but don't need to return anytime soon. Â
What we much prefer is Alentejo and could spend 5 nights there easily--we enjoy vast expanses of olive, Â horse and cork farms, the charming towns of Evora, Elvas, Estremoz, Beja, the marble town of Vila Viçosa, the eagles' nests fortified hill towns of Marvão and Monsaraz, the simple country cuisine. The heat is oppressive in summer, however but tolerable in May.
Obidos is far too touristy for me--it could be just a short stop on your way to Tomar. Â We loved our 2 night stay in Tomar and the visit to the Convent of Christ of the Knights Templar.Â
Coimbra was a 2-night stay for us but we could have done 3, as it felt rushed. Â We did the tour of the University and the ruins of Conimbriga and were very impressed with the National Museum of Machado de Castro where we spent several hours.
I remember that we "talked" about the Douro quintas--another lovely quinta choice just outside of Pinhão on the right bank could be the Casa Visconde de Chanceleiros.  There are some spectacular viewpoints in the Douro that we enjoy- Miradouro de São Leonardo de Galafura, Miradouro de Casal de Loivos and the drive up to the town of Ervedoso do Douro is spectacular.  Lamego is a nice town to visit on the way for the town itself and the  drive up to the Santuario de Nossa Senhora dos Remédios with its tiered staircase of 868 steps above the town on the Monte de Sâo Estevâo hill.
Guimarães is a charmer---3 nights is perfect to visit all the sights there, day trip to Braga and you might want to visit the Citânia de Briteiros as well, the well-preserved archaeological site of the Castro culture. Â We adore the Minho, especially Viano do Castelo, which you could do in a day trip and it's fun to visit the huge bi-monthly market in Ponte de Lima and also the market in Barcelos.
When we visit Porto, coming from the Douro we always stay for 4 nights. Â It's become a favorite.

Just some initial thoughts..
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Edited to add that I don't know why my first paragraph appeared twice. Â I've been away too long and am having a hard time writing! Â Just a thought about Obidos--it would be a one-night stop for me at the very, very most, as it's small and can be seen in a very short amount of time.

Thank you so much, Maribel! I just purchased my tickets! So, fingers crossed, it will be happening!

I appreciate your thoughts and will stick to my gut feeling and stay in Tomar (2 nights) and Coimbra (3). I'm intrigued by Alentejo and will definitely look into staying longer in this region.

And I'll have the time to look at the Douro quintas -- thank you, again, for the wonderful descriptions!

I'm excited!

Another Portuguese city that we enjoyed, somewhat under the radar, is pretty and well kept Viseu, which was on our way from Evora (Alentejo) to the Douro. There is a lovely Pousada there to which I would love to return.
A great resource for Portugal travel planning and ideas for me has been the Julie Dawn Fox blog, filled with ideas and great insider information. https://juliedawnfox.com

The Barcelos market on the Campo da Feira occurs every Thursday. The enormous Ponte de Lima market is held every other Monday.

Maribel, again, thank you! I remember following Julie Dawn Fox’s blog 2 years ago and will use it again.

So many wonderful ideas. I just looked at the Casa Visconde de Chanceleiros site, and it looks wonderful! Now I just have to get out my actual itinerary so I can start booking things.

Hi Progol, I am happy to hear you are finally going to Portugal. I also remember when you were planning your trip in 2020. In 2018 we spent 5 nights in Lisbon, and that included a day trip to Sintra, so those are the only 2 places I can comment on. I think 3 nights in Sintra is awesome, and 5 or 6 nights in Lisbon is perfect, too. It's a wonderful city and one of the smaller capitals, so it's easy to get around and I don't think you will feel rushed with 5 or 6 nights. There were a few places we didn't have time to visit, but for the most part, we did everything we wanted to do. I would have enjoyed a couple nights in Sintra but visiting it as a day trip was better than not visiting at all. You might have already read my trip report. If you like seafood, one restaurant I can heartily recommend is Cervejaria Ramiro recommended by Anthony Bourdain. It was the best meal we had in Lisbon. We also really enjoyed eating at the Time Out Market.

https://www.cervejariaramiro.com/
https://www.timeoutmarket.com/lisboa/

Karen,
I highly recommend Cervejaria Ramiro as well! We have an upcoming dinner there next month. I learned that one can reserve a table by email so long as diners arrive by 7:30. Afterwards one may have to stand in line.

We did not make reservations when we were there in April 2018, so we did have to wait in line for about 40 minutes.

@Maribel and @Karen, thanks for the restaurant recommendations - they look great! I’m thrilled to be planning again for Portugal!

@Michael, thanks for the lovely photo of Obidos. I’ve decided to stay in Tomar but will try to stop by on the way.

@HappyTrvlr, I’m glad we will have the time for Guimaraes and around. It looks like a lovely area and interesting history, too.

Well, I think we'll stay in Obidos so we can talk about it after we both get back. I know it's touristy, but probably/hopefully nice and quiet at night.

I warned friends of mine that Obidos was super-cute and very touristy, and they decided to stay there anyway. Afterwards they said it had been a mistake. Of course, it might be a bit quieter right now. Next year, maybe back to pre-Covid.

It sounds like the nights are wonderful and we still don’t know if the pre-Covid crowds will be back, especially when you’re going.

I was drawn to Tomar anyway, so am not planning to stay in Obidos, but I do wonder about whether the pre-Covid crowds will be back anytime soon.

We vacationed Portugal on three occassions, all in May/June and always had perfect weather. Sounds like you have a lot planned for your trip and are traveling some distances. We did the Algarve after a week in Spain and really enjoyed the beaches and the towns (stayed in Praia da Luz) of Lagos and Sagres (spectacular). Lisbon has lots to offer although I think 4 days is plenty. Evora was great with Roman ruins and the Chapel of Bones. Evora is good size but not city big and the crowds were minimal. We loved Porto and its a favorite over Lisbon. We did Porto by rail from our base in Guimaraes. Loved Guimaraes, LOTS of history and some great easy day trips (Braga, Porto, Bom Jesus Sanctuary). Sintra and Obidos were easy day trips from our favorite villlage/town in Portugal: Ericeira, a wonderful, beautiful old fishing village with great views, beaches, restaurants, ect. As other folks have mentioned both Sintra and Obidos can be over run by tourists. Obidos can be seen in 4 hours. On our last trip to Portugal (2019) we stopped in the Azores for 5 nights on our return to Boston and really enjoyed the Island of Ponta Delgada.

Thanks so much, Mike!

I’m pretty sure I’m eliminating the Algarve from the itinerary though now trying to hone in on the itinerary. There is so much to see that it’s hard to narrow it down. I’m also pleased to hear that you love Porto - the many positive comments have given me a good feeling about the city.

Ericeira sounds lovely and I’ll look at it, though I imagine for first-timers, it’s best to stay in Sintra as I don’t want to have a car right away.

A third recommendation for Cervejaria Ramiro. Also enjoyed meals at A Cevicheria, Taberna da Rua das Flores and lunch at the big Mercado.