First Time Leaving Home / Traveling : Help!

I can help with the Portuguese Camino part as I have walked this section twice, from Porto. There are plenty of albergues to stay in that are reasonable, price wise and very clean. I have never found a dirty one and I have now stayed in dozens and dozens of them. You should probably post something over on the Portugal forum. Or click on my name. There are multiple posts on that section about walking this Camino.

I have never travelled on the Camino. It's a dream to walk part of it and will probably stay that way. I found this stie years ago - The Confraternity of St James https://www.csj.org.uk/ As you can see it is UK based but has good information.

From the little I know you need to be fit enough and need to have well broken in hiking boots/shoes. I think the routes through Spain are very hilly.

On a separate but related note, years ago, I read a blog written by Oliver Shroer it was about the journey he and his friends journey on the Camino through France and Spain. During the trip he recorded sounds and music. The Camino album is wonderful. Not even close to punk so may not be to your taste.

I wouldn't book internal flights yet. First, I would figure out when you will do the Camino and book that, as well as your accommodation for the set dates in Madrid and Vienna. It makes geographic sense to group the Camino, San Sebastián and Madrid, and starting the trip with these three makes some sense, but if you decide to do the Camino later, maybe after Madrid, then that changes your starting point.
Another big consideration is your transatlantic flight. Don't get hung up on flying into a particular city or figuring out how to make a round-trip ticket work. You can buy what is called an "open jaws" ticket (fly into one and out of another city). With your trip length, it might make more sense to buy two one-way tickets. As you pointed out, Paris-Vienna can be done for under $100, so you don't necessarily have to buy a connecting ticket. Skyscanner.com is a great way to find low fares. You can search from your home airport to "anywhere" and choose the first European destination that comes up. This is usually London, Paris, Amsterdam or Frankfurt, but not always. Portugal has TAP Airlines, which often has very good fares. If you find a cheap ticket to a city you hadn't thought of visiting, take a look at what's there or nearby and how connect to your preferred destinations. You never know what you'll find.
A great resource for getting between cities is seat61.com, which has all the information you need for train travel.
When planning a trip, I use a spreadsheet with columns for date, mode of transport, accommodation, sights/activities and restaurants. Use some kind of color coding for things that are booked. At first, I put everything in--everywhere I want to go, everything I want do. Some things get struck off the list because time is not limitless.
Once you have identified the places you want to go, figure out a sensible order for them and look at the connections between them (plane, train, bus).
As far as playing it by ear, you won't find a lot of folks on the Forum who do that, but I think it will be easier in April and May than in high summer. One option is to make reservations that can be cancelled or changed for free or for a nominal fee.

Susan, I am 70 and just walked Camino #6 in 2024. My first one was at age 60 and I walked for 4 weeks. In 2023, I walked for 7 weeks. There is a Canadian pilgrim group. Do spend some time on the Camino forums or FB pages for info about boots, shoes, etc. You don't have to be super fit to to do this as you can walk as little or as far as you like each day.

summer, welcome to the Forums!

March 25th to June 2nd (are you flying home on June 2nd?) is 70 days. That's starting to get close to the 90 day limit in Schengen countries.

Are you aware of the Schengen laws?

It sounds like you’re doing some good planning for a great trip! Regarding specificity of planning, things have changed since I was your age decades ago when our only planning ahead was buying a copy of Let’s Go Europe and a rail pass, but with the length of time you have I wouldn’t try to plan all accommodations or other arrangements in great far advance detail. Two one way flights are often much more expensive than a “multicity” (also called open jaw) round trip in which you fly into one city and leave from another. In general, flights within Europe are typically more expensive the later you book, but airfares are constantly changing. San Sebastián is great, but a week there is quite a long time. It is a major resort and can be pricey, although being there before high season might help in that respect; but a major reason that spring isn’t high season is that it’s not beach weather yet, and beaches are a major reason SS is so popular. Good food, yes, but that is also true elsewhere in the region, and you might want to look at Bilbao for at least part of your stay in the Basque region— I haven’t been there but it gets a lot of favorable mention on this forum. If you’re going to Vienna try to visit Budapest, not far away and a big favorite with younger travelers for its lively ambience and relative budget friendliness.

Shifting some of the time you have penciled-in for San Sebastian to Bilbao is a good suggestion. Bilbao is much less touristy (therefore probably cheaper) and has a larger medieval district, though it's a bigger city.

As others have hinted, that $30 airfare will probably not be available when May rolls around. Airfares are volatile but trend upward; that flight could be $120 + luggage charges in a few months. Sticking to an itinerary with primarily short hops that can be taken by train (even better if by slower, cheaper regional trains) will help keep your transportation cost down if you want to retain flexibility by not booking things far in advance.

I love spending time in some of Europe's smaller cities. Lodging, food and entry fees are often cheaper, and you probably won't see as many Starbucks, McDonalds, etc., outside the very largest, most popular cities.