Winging It in Portugal?

It is possible to "wing it", but I would at least have a hotel reservation for the first city you intend to visit. 2 nights minimum. That way, you can settle down and have some time to adjust before thinking about booking the rest of your journey!

Also, I wouldn't "wing it" in the traditional sense of arriving somewhere and looking for a room on the spot. Few people do that these days, and some hotels (especially chain hotels) can have dissuasive walk-up rates. With internet access, it is easy to book your next stay while you are on the go, at least the night before you leave. I would avoid same-day bookings: they can be stressful.

Other comments:

• October isn't the busiest month so you should be able to find beds everywhere, but check for local festivals in your intended destinations. If there is one, book ahead.

• Be OK with the fact that you won't get to sleep in the hotels with the best value for money. You need to be able to either spend more than you intended, or settle for lower standards of accommodation.

This is a matter of travel style, and I fear you two may not have the same style. It's also the way students traveled in the 1960's. I think it's less common today. It will take time away from sightseeing to do the bookings, and you may have to pay a walk-up rate or go farther to find a place with room, before you can even scope it out from the exterior. I know people believe that Hotels dot com has cheaper places at the last minute, but are you staying in real hotels?

I would not do this, but I'm 71, and there's no reason another person should do it my-way.

I have never had the experience of being sorry I went to particular city, but my wife and I both dislike frequent hotel changes, so we book 3-night minimums, and take train daytrips if the city turns out not to have quite enough to see. Sometimes packing, unpacking, copying passport data, and getting (?) cash to pay a tax-evading B&B can take more time than you think. Opinion.

Some of the sights in Portugal, like Roman ruins, Templar castles, monasteries, and so on, are quite spread out. I am sure your boyfriend will be horrified by my post elsewhere
https://community.ricksteves.com/travel-forum/portugal/7-nights-in-lisbon
about using a BUS company TOUR to hit three or four high points in a full day out of Lisbon!

I am sure your question has come up here before, at least in the general case. See Search box top center.

Edit: If you go to the TI to see their list of low-cost lodgings, you may have a low-cost teenager behind the desk, who has never met a single owner who posts their room at the TI. And if the TI is closed today?

There's no reason you can't scope out what's on offer in advance. I use Booking.com, and you can save your favorites there. At least then you have a sense of the types of accommodations available and sort of be on the page about what types of places you prefer to stay. I would certainly have the first stay booked, but I can see the appeal of not having all three weeks planned out. But NOT without research and backup plans--a hybrid approach.

You probably have an idea of the cities you most want to visit. Now is a good time to look for hotels that suit your needs (location, amenities, price) and see if they have rooms available on your approximate dates. At least you'll have an idea of what's likely to be available. Also, if you decide - as recommended above - to book 2-3 days in advance, that's pretty much when you arrive at each place you'll be booking the next one, so you still aren't winging it.

I've very rarely been in a place that I wanted to leave earlier than planned, but I'm often glad I have a booking for the next place, forcing me to leave a place I haven't seen enough of - just so I get to see more. I think even people who wing it do a lot of planning in advance and have a very good idea of how much time they want to spend in a place based on what they want to see and do there. From reading this forum over quite a few years, I have the sense that people who do travel more spontaneously are people who use rental cars, so they have more flexibility - if this little town doesn't have a place, I'll just drive another 30=40 minutes to the next place.

I’m going to portugal in late September and I am seeing that some hotels I’m interested in are sold out or quite expensive for dates I’m looking at. So I think especially for Lisbon and Porto at least, it might make sense to book hotels with free cancellation and that would give you some flexibility but also ensure that you have a place to stay that needed your requirements if you do want to go to those cities.

October can still be busy, particularly when it’s half term holiday for much of Europe. I have always pre booked so haven’t tried booking on the hoof.

If you aren’t fussy about budget or location, then you can probably find something, but if you are more particular or don’t have a car, then it maybe best to book at least a few days in advance.

5th October is a hollyday in Portugal. You should book your first days. From there, I believe it's ok to "wing it". October is quiet enough for that.

I would definitely book your first and last hotels. You don’t want to be searching for a hotel the day you arrive. Similarly, you know the city which you will fly home from and you want to be within a reasonable distance from the airport.

I used to do this all the time before the internet. The upside is flexibility. The downside is that sometimes you end up paying more for accommodations or need to stay in a location that is not as desirable as you’d like. You won’t find yourself sleeping on a park bench as you can get online the evening before you check out of a hotel and book your next accommodation.

I agree with booking first and last day(s). I have been cycle touring in various European countries since 2014. In 2014, we cycled into town, spotted a hotel, and asked if they had rooms. If not, they usually found us one at another hotel. The advantage was it eliminated searching for the booked hotel by bike. However, with services like booking.com, we now usually book the night in advance, perhaps longer if it's a larger city or weekend. The mapping apps are now good enough to find the hotel. Our current favorite is Organic Maps, formerly maps.me. (free). Just download the maps to your phone so you can navigate off-line.

Reserving well in advance will give you better-value lodging, and the best ones will often be unavailable at the last minute. However, we preferred the flexibility to change routes in the event of poor weather, sickness, tired rider, or just the desire to stay in one place longer. As cycle tourists, we are really looking for modest but clean accommodations, and every place has internet. (wee-fee). We prefer to spend the saved money for better restaurants.

The Lisbon Marathon is Sunday, October 9th. You may find higher hotel prices that weekend (I did in some cases) or perhaps even difficulty finding a room.

I've done the "wing it" approach many times on my trips to Europe including to Portugal. It usually works for me. But, I would do some research ahead of time e.g. on the Booking.com site and pick two or three places in a city where you might like to stay if you were booking them right now. Do a little research on the parts of town. This might be most important in say Lisbon which is pretty big. Also try to check various dates and see how booked up the town is on those dates. Let's say you are in Lisbon October 15 and are considering getting to Porto around October 22. So...check for hotels on Oct 22 for 4-5 days right now. How busy is it? If Booking.com says, "80% of rooms are booked for those days...you know something is probably going on there so the town might be booked near the last minute. Or, maybe availability between Oct 22-27 is wide open, so by the last minute it might still be. Make some notes, add them to your research for each town.

Then when you are in Portugal, when you are about to book something in the next town, you won't have to start from scratch if you've already researched it. Maybe one or two places you had picked is still available and you can just book it the night before. Maybe not...so have a second and third choice in your research.

I am currently in the latter part of 3 weeks in Portugal. I have been winging it as far as transportation, booking train or bus tickets s few days in advance. No problem with that. Hotels I have locked in. I have also not booked things in advance as far as activities which has been a problem due to being sold out (boat tours in Lagos, megalithic tour from Tavira, etc.). Of course, as many mentioned, October is less busy. September has been busier than I expected.

I have traveled quite a lot overseas, having lived for 9 years overseas. Also, have visited 81 foreign countries.
I have taken bus tours, river cruises, ocean cruises, done my own thing, taken day tours and more.

If you are doing it on your own, it is best to PLAN. Planning helps you determine how much time you will have to see what you want to see.
If you don't plan or research what to see and where to go, you can easily miss something special.
Also, if you are traveling from place to place, you won't know how much time it will take to go from A to B. In fact, you won't know the best mode of transport.

October is not a real busy time, but so many people travel these days and some items require a booking or you will risk not seeing it.

As for hotels, this item is THE most important item to book in advance. In my travel experience many years ago, I planned to visit a city and just showed up there with no hotel reservations. Guess what, there was a festival there and every hotel was booked for miles around. That ruined our weekend.

Planning is fun, you get to anticipate what you will see and it is exciting. Don't wing it.