5 weeks in Portugal

I haven't gone at that time of year, but in general, you are likely to find the most attractive (luxury, Pousadas, renovated convents, and so on ... ) to be unavailable as "walk-up" bookings. Is your budget very limited? Do you need air conditioning? I'd check some climate sites for temperature averages on your travel dates.

I am not telling you what to do, but if I were spending five weeks in Portugal, I would spend a few days in Madeira.

Jense,
5 weeks is a lot of time. I'm jealous.

I have a few questions if you don't mind
Is this your first visit?
How meticulous a planner are you in general?
On previous trips, did you prebook?

Our 4 trips to Portugal have all been 2 weekers and we prebooked as one of us (I won't say who) is very particular about accommodations. But as the trips were centered around Lisbon, it did not make much difference.
Years ago we visited England and booked a car. We also prebooked all accommodations. As luck would have it, we loved the first town we visited (Evershot in Dorset) and regretted being locked into leaving after only 2 nights.
If you are flexible people, I suggest you prebook your arrival stay in Lisbon and maybe a couple of nights on the road.

btw, if we had 5 weeks, we would definitely include the Azores.

Regards,
Dennis and elinore

In mid-September 2023 we spent two leisurely weeks in Portugal, but had all hotels booked. With a rental car we wanted lodgings with on-site or nearby parking. While we had a couple 1-2 night stays (Nazaré and Óbidos) we used the other locations as bases and took day trips from them. It doesn’t take a lot of time drive between most locations so many day trips can be within an hour or so of your lodging location.

We have never been to Portugal before. We prefer to travel with flexibility so we can stay longer in more interesting places or move on if we are not enamored with a place. However, when traveling in high season I will fully book our trips and then it feels hurried. We will be renting a car and likely stay at accommodation for a few days to a week if we can use it as a home base. We tend to like off the beaten path areas for portions of our stay. We usually try to book places in the $150US or less for most nights but willing to splurge on special places, such as ocean side or historic hotels. I have already noticed most places are booked in the Lisbon and Porto area for September on the major booking sites so will book those cities. Is anyone aware if there is potential for local hotels that would have availability on a few days notice?
Tim: Historically the weather should be pleasant so AC may not be required in the north. dkg: We had planned on the Azores for a week, but decided to make that another trip so we can spend a longer time so we could explore several of the islands. Any suggestions for your most favorite small towns to stay in?

Sorry, we didn't see a lot of small towns. We did enjoy Guimares, because we were in an historic, air conditioned Pousada, which was within walking distance of the modest cable car up the mountain. The weekend was a real community outing day to that mountain, a real Rick Steves experience.

Now, this was 30 or more years ago, but to our astonishment, as we approached Guimares, we passed, let's say by the city walls, a shaded municipal hand-laundry facility, with about 20 tubs, and we saw people doing their laundry there. The tubs were some kind of cast stone, not Home Depot laundry sinks.

We used the car to see the Bom Jesu pilgrimage site, and some out-of-town Roman sites, with great mosaic floors, if few standing structures. Also a castle of the Knights Templar, well-ready for tourists.

Although you might still have a chance in Portugal, I think the idea of finding forgotten towns that Band of Brothers just left is a fading phenomenon.

A nice hotel we stayed at in Penalva Do Costello was Parador Casa Da Insua. It September 2023 it was €335 for two nights, including a breakfast buffet. It’s in a restored 18th century building with an on-site museum. From it we took day trips to Viseu and Lamego, and a quick stop at Dolmen Cunha Baixa.

Other places we stayed were Coimbra, Tomar, Nazaré, Öbidos, and Porto.

We loved our road trip through Portugal…every stop along the way! Consider stopping in Marvao and Monsaraz en route from the Douro Valley south. These gorgeous, medieval towns were highlights for us.

We have not fully booked trips in Portugal twice and been fine, but both times were before Covid and in April, so I can't say if it applies to now. We did in italy in October in 2022 as well. My gut is that you would still be able to find places in the smaller towns. For Italy I actually used an online guidebook to help locate on short notice. For Portugal I think mainly booking.com, and would make sure we had a place the night before.

Check ahead of time for holidays, etc, and make sure those are booked. Weekends can also be harder.

If you can book the most wonderful B&B ever in Porto. It is called The InPatio Guesthouse. It is in a great location, wonderful owners, spacious rooms, super breakfasts and super service.