If you share your travel plans with the community I am sure that you will get good help to fulfill your travel deam. 

May is not high season for holiday travels so the trains are less likely to be full.

It can look a bit overwhelming at first glance, but once you get the hang of it, you shouldn’t really worry.

You can reserve a lot via the interrail/eurail services, but it just costs a bit more.

Some countries are a bit more annoying to interrail, with lots of mandatory and relatively costly reservations. Some you can’t even book them online. France and Spain are notorious about this. Perhaps you should keep these for the later parts of your trip, once your more rail savvy it’s very doable.

Central Europe (Germany, Austria, Switzerland, Poland, Czech Republic,...), the Benelux-countries and the UK are usually good places to start and help you become more rail-expierenced, before tackling the “harder” ones.

May is a good month, weather can be nice already, everything is lush green and flowering because of spring, and absolutely not as busy like in summer on long distance trains- although there are quite some official holidays in May, depending on the country. - usually in catholic countries.

Longer weekends, means holiday plans for a lot of people which in turn means busy trains. So you might want to work around those in your planning ;)

It really differs an awful lot per country-after all 33 different countries participate and all have the heritage of their old state-run burocratic state railways-some have modernized quite succesfully, other less so.

Also-having myself travelled extensively in USA on AMtrak (and various local commuters-I guess even far more as you have ever done) and in CA on VIA and more-and following forums like this and others for some yrs-USAers tend to be grossly overworried and make problems about the tiniest things that noone here really cares about.

Easiest countries: NO RES always needed, plenty of trains, good comfort-in travel most will speak passable bad english-where all the extra hassle is near zil: GB, NL-BE-DE-CH-AT-CZ. Or more or less the central countries seen on the map.

FR and IT want you to RES and pay extra for their superfast hi-speed trains-on most routes even fairly easy to avoid, but USA are brainwashed to think ´time is money´ so decide if that is true. The common error then is that you want to do that far too long in advance.

In the past there used to be plenty of ´howtodo´ guideboox-more aimed at young students in gap yrs-many by a guy named Steve …, perhaps your local library still stocks the odd one. Good info aimed at your folks.

Travelling with a Global Pass is a great adventure, but obviously one needs a certain reality check on self-planned travel and managing your own train travel, whether that be by buying tickets as you go or using the Global Pass. If you are used to planning your own trips (travel, accommodation, excursions/tourism plans etc) you are 90% of the way there

Unlike the original Interrail/Eurail passes which were only available to youths on a back-packing trek, the current passes have expanded into an economic way for all to experience Europe without flying or driving.

The original pass was (and still can be) paper based and it was simply a single “Ticket” where you listed the train on the sheet to validate it for that journey. Virtually all trains were open seating and reservations hardly necessary.

Today the majority of pass users use an app on their mobile phone and, with the advent of high speed rail, many fast and long distance trains now require reservations, which are not included in your pass.

The change to using an App is fundamentally the same as the paper pass - you add the individual trains to your pass and you can travel on that train. The app however is a little more complicated than getting a pen and writing it on a sheet of paper, but that is what you are doing. Once mastered it is as simple as the paper pass.

One of the key things is understanding the processes involved in the app, which is actually four related tools in one - A train planner/timetable, a reservation tool, a trip manager (diary) and your actual pass.

So in summary do not be intimidated as long as you are confident that you are able to create an independent holiday, where the pass is only a replacement for buying the tickets in advance, not the whole thing.,

Re reservations, If it helps, Imagine a low-cost airline offering you an unlimited flight pass but you have to  let them know which flight you want so they can keep you a seat at a nominal management fee.

If none are available you have to choose another flight, but they will let you on as long as seats are available.

That is how the majority of the train companies operate with their fast and long distance trains. Some say there will only be a limited number for pass holders, but they are relatively few and seats are available on all but peak time trains in high season. 

I hope it is suitable for you because it is a great experience as long as you do your own thing and don’t try to spend all the holiday on trains. Always allow time to fully appreciate the destinations and relax before your next move.

I agree with all the previous comments. Obviously I have done a lot more travel than you and I am also in my sixties. My wife and I have travelled over 10000km this year with very few problems. If you make the travel part of the holiday you will enjoy it so much more! Trains can be late but nothing like those you can experience by plane. It is unlikely anything will go wrong but if it does you speak English and you can always find someone to help (unless you are deep in Eastern Europe). You have a credit card and a lot of life experience so relax! This community forum is followed by absolute experts who can give advise if you need it. My key tip is to read the section on this site about how to reserve and learn how to use the websites of the national rail companies. Do not use the Eurail app.  to reserve but it is great for general planning.

Thank you AnnaB. Your comments are helpful and I appreciate your thoughtful response. 

My wife and I are grateful for those who took the time to respond. We found valuable ideas in each response. Your recommendations and insights helped bring clarity, and instill confidence that we can do this!

After we digest your comments I am sure we will reach out with some refined questions. It’s great to have an experienced community to learn from.

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