Please help me figure out the Eurail?

If you are unfamiliar with European rail travel go here and start reading up on it: www.seat61.com

If you are the kind of person that wants to book everything months in advance you should not get an Eurail pass. That is for people who want to postpone their detail planning till they are here. And be aware that July is ages away. Many trains cannot even be booked that far in advance.

Trains in Europe are mass transit. Do not overthink them. For most trains taking them is as trivial as riding a subway...

If I buy a Eurail pass, how will I know which trains/tubes/metro I can actually use it for?

Basically, no tubes/metro. Trains only.

Eurail isn't a train system or a booking agency. You can't book trains with Eurail. You can only buy a pass from them, which, as another commenter mentioned, is probably not the best option for you. It also doesn't cover Eurostar if you plan to use that to get from London to the continent (which you absolutely should--and that might be available for booking now). I agree you should start by reading Seat61.com to get an overview and then to drill down into your plans.

It also doesn't cover Eurostar if you plan to use that to get from London to the continent (which you absolutely should--and that might be available for booking now

It does include the Eurostar from London to Bruges (well, to Brussels then Belgian IC train to Bruges), but you must buy a separate seat reservation. Same applies to Eurostar or TGV to Paris, TGV to Germany. When you book a ticket outright, the seat reservation is included in the ticket price.

An Eurail Pass is great for last minute travel if you want to be flexible. For European citizens there is the Interrail Pass which is similar. I am currently in Amsterdam, on my 4th pass in a year...

For me it is easy. Most of my travel is last minute. A flexible return ticket Interlaken Amsterdam in 1st class is 999,60 euro. A pass is cheaper here, even if I do not use all the days.

But if you buy your tickets months in advance you can get very steep discounts, and get that same Interlaken - Amsterdam trip for as low as 59,- Cheaper than a pass day.

The problem is France. In France passholder reservations are expensive, and often hard to get, so that makes a pass not very suitable for trips through France.

So:

Book London - Brugge and Brugge - Paris with the Belgian Railways (www.b-europe.com). You can book these already now. For trips within Belgium just buy tickets at the station, online or using the app. Domestic trains in Belgium are basically commuter rail. Its like riding Metro North or NJ Transit in the US, or the Melbourn or Sydney trains in Australia.

Paris - Gengenbach you best book with the Deutsche Bahn (bahn.de), but you may have to wait a few months. If you try, and nothing comes up you are just to early.

(Note, why not book with the French Railways? Well, they have completely screwed up their booking system, and cannot book combinations of international and foreign domestic tickets. So they cannot sell you tickets to destinations that are not reachable by direct train, ie, most places in Europe...)

In the Black Forest area you apparently are given a pass that gives free local travel. This pass AFAIK goes as far as Basel in Switzerland.

Then for the Swiss Part maybe look at getting the Swiss Travel Pass or the Half Fare Card, but that is a different topic...

IMO you feel overwhelmed because you have undertaken a pretty overwhelming trip and your planning task is similarly overwhelming.

An important question first... Have you locked in your accommodations, and are the appropriate rail stations for your "many" day-trip destinations sufficiently accessible?? It is not easy to find accommodatons for 5 that are near an appropriate station for whatever day trip you are doing.

In a small town like Gengenbach with a limited # of accommodations, there may or may not be a bus stop nearby if you are on the outskirts of town somewhere because you couldn't find a place for 5 in town; it might in fact be best to stay in a nearby town if a suitable apartment etc. is near that town's station. That said, any apartment that's in town will be a few minutes' walk to the town's ONE station. And of course, ticketing is irrelevant here because of the KONUS card - yay.

In a place like Paris, housing 5 people near a station may be problematic too, and aren't there like 6-7 different train stations? And if you'll be daytripping by train out of Paris to visit the D-Day beaches, or to Chartres, advance-sale p2p tickets are typically non-refundable, so ticketing from the correct station and nailing down access to that station (bus? subway?) in advance seem critical elements before purchase of the p2p tickets. I would want to lock in my lodging prior to any such purchases.

Thanks for the correction, Sam. I'm not sure where I got that information about Eurail not covering Eurostar.

IMO you feel overwhelmed because you have undertaken a pretty
overwhelming trip and your planning task is similarly overwhelming.

Ditto what Russ said. If it were me, I would break down the entire trip into more bite sized pieces so you can get your head around what you need to research because there are indeed different requirements in each place. Then figure out what you can/can't buy ahead of time and the process to do so. Here's a way you could do that for London - this is just a rough example not exactly what you should do, just using it to illustrate my suggestion.

• Arrive London Heathrow airport, transport to accommodations (due to jet lag and so much luggage and people, maybe a private hire van? Definitely book in advance - oh and don't forget to get an ETA for each family member ahead of time or you won't get past passport control)
• 9 days transportation inside London on tube/bus (use contactless credit card for each adult (though research if a weekly travel card would save $), research requirements for children and buy any Oyster cards with child discount at Heathrow on arrival)
• Day trip Windsor (tube then train, research if you need to buy in advance, if so note how many days ahead they go on sale)
• Day trip Bath (tube then train, research if you need to buy in advance)
• Transportation London to Bruges (multiple trains, probably Eurostar to Brussels and then local train to Brugges, definitely book what you can in advance, Eurostar may be available now and only get more expensive as you get closer to travel dates)

Then repeat for all the places you're going to. As some tickets go on sale in specific time frames (e.g. 30/60/90 days ahead) plot all the advance purchase dates out on a calendar so you don't miss one. If you're not already using something like TripIt to keep your travel info in one place you might want to do that so you have a place to store all your information gathering.

Good luck, you've got quite a task ahead of you.

The European train system is somewhat like the German language. If you grew up in Germany and your mother and father spoke German, then you are proficient in German. But if you are an American on a 2-week holiday in Europe you will never become proficient in the European train systems without taking a lot of classes before you travel. The overall complexity of the European train system might as well be Chinese or Hungarian. Even our few in-house experts often disagree … and they are German.

The advice above is good. Take one leg at a time. Research it today, make a list of the links for booking with the national rail lines. Then maybe a month prior, start buying tickets. The local forays for day trips, etc, you can buy once you are in the country. The short hauls generally don’t cost much (if any) more on the travel day. But the long hauls will be significantly different.

Oh, you started by talking about rail passes. Yea, good luck. Do a bunch of research, filter out a bunch of conflicting opinions and you might save a few dollars. Well, you would probably save. But it’s so much easier just to buy the freeking tickets unless you are planning on a trip where each day you wake up and decide if you will stay put or travel.

Eurostar tickets are currently available until early September, as a for instance.

Depending on date and time July fares start at £57. Not only are passholder places limited on any specific train, you pay a €35 reservation fee with Eurail.
Thus there is good reason to buy London to Brussels as a point to point ticket, rather than have it covered under Eurail.

London to Windsor is only about £17 return (after the 5% or so fare rises in March) so it is doubtful you would want to use a pass day for that fare.

Ok thank you so much for the very helpful and in depth information! This has already eased my mind a lot. Breaking it down place by place is a good idea and where I will go from here. I just didn't know if all of the countries worked together with the trains or if I needed to use a different website/company/app to purchase my tickets for each country. Eurostar sounds like it encompasses a lot of train travel across multiple countries, but might not be the most cost efficient compared to buying tickets directly from each country's respective train system, if I am understanding correctly.

Thank you for the websites and info on where to look in each of my stops, I really appreciate that!