Milan > Somewhere by lake Como (perhaps Varenna?) > Tirano > Chur is a very easy straight shot without any backtracking.

From Chur you can take a bus operated by the same railway company, Rhatische Bahn, to Lugano, then another fast train straight back to Milan. It makes it easy to do the Bernina Pass as a circle. From Milan there’s plenty of connections to Venice. If you organise it right, you might be able to leave luggage at your hotel in Milan.

Eurail passes are accepted on the bus, and reservations are required.

But then if you want to visit Zurich, Chur is very close.

On to your other destinations, you have a lot of Italy in there, but will you visit Siena? It seems like it would fit what you’re looking for.

I would probably choose Prague or Brno over Vienna anyway, but maybe that’s just me!

Leipzig and Utrecht are both great cities, smaller and so easier to get around than Berlin or Amsterdam. These are both a long way out of your way though.

@ralderton the Bernina Express bus runs from Tirano to Lugano so from Lake Como side/Italy.

They could however travel from Chur to Andermatt (part of the Glacier Express route) and then to Lugano (Old Gotthard scenic route) to avoid back-tracking.

Thanks for your suggestions. I’ve tried to incorporate them into my planning but just need a final confirmation of whether the alps loop I have tried to include is the right way to go.

It sounds like there’s no super-outstanding place that we haven’t listed and your observation about Berlin or Amsterdam (and the alternatives) being a long way out of our way is what we thought too so we’ll probably forego them.

I’ll try to build a trip to Siena into our Tuscany travels. From what we’ve seen there are so many things to see in Tuscany, so we may just have an extended stay in Florence and do day trip(s) to Bologna and Siena, then end our stay with a trip to Pisa (an hour or two) and on to Cinque Terre, where we can spend a night.

From there I tried to plot the various options you both provided and came up with what looks like a circle route and wondered if you thought this would give me a good view of the area and was workable - perhaps too long on a train without disembarking???? 

Milan>Como (stay a night or two in the area before starting the round trip)

>Andermatt (doesn’t seem to show up on the planner)>Chur>Tirano>Varenna (Maybe stay the night here or go back to where we spent the previous night to pick up our luggage)>Venice…

After that, and our stint with family around Pordenone, I think we might stay with the original plan going to Vienna>Prague>Zurich>Basel>Mulhouse>Dijon by train. 

The other area we were told was beautiful was the drive from there to the outskirts of Paris via places like Givry>Bourges, Loire Valley, Le Mans. Apparently there’s lots of famous Chateaus and scenic spots to see.

We will conclude out trip with a train ride to London and spend a few days there.

Hopefully that will make for a not-too-crammed trip. Does that sound workable?

For Como-Andermatt, where on Lake Como will you be starting from? If it's the town itself, make sure you are selecting the correct station. It will be from Como S. Giovanni. The train back from Tirano and Varenna doesn't pass near here though.

I see plenty of connections to Andermatt, some use the Eurocity, and require a reservation. Others stay on regional trains and don't need reserving. They all involve two or three changes.

‘’Thanks for that.

I haven’t made any accommodation arrangements for the whole trip yet. I want to work our where I am going, then plan the accommodation to suit

You said: “They all involve two or three changes.” Based on that, would you recommend changing the plan? I thought this option my include the suggested “part of the Glacier Express route” which seemed appealing.  But if it’s going to be too complicated, I can just use the bus option you suggested. 

Sorry to be a pain, but this is my one shot at getting it right.

Not a pain at all! Feel free to ask more questions if anything’s uncertain. I quite enjoy planning itineraries!

I guess it depends how much you want to see Lake Como, and which part of it appeals.

Perhaps one way to avoid so many changes would be to skip the visit to Lake Como on the first part of your circular trip, and go straight from Milan to Brig* on a direct Eurocity train. There you pick up the Glacier Express towards Chur and the Bernina Express to Tirano.

All connections in Switzerland will be easy, and will run like clockwork!

On your return from Tirano to Milan, you can spend some time in Varenna and explore Lake Como from that side. Varenna is gorgeous, and you can take ferries to various parts of the lake such as Bellagio and Menaggio, 

This also allows you to leave luggage in Milan if you wish.

-

*Other options instead of Brig are possible, but this gives you a fast ride on a good quality Eurocity train from Milan (you’ll need a reservation), and lets you pick up the Glacier Express route straight away, without further changes. It’s further west than Andermatt, so the overall journey time to Chur will be longer, but it gets you more of the Glacier Express route.

You should be a travel planner, if you’re not already!!

Thank you for your ongoing help. Since you don’t mind I will continue this question and see if I can finish planning the trip wile taking advantage of your local knowledge. Here’s where I am at the moment. Times based on a quick look at Google Train plan. Any suggestions would be appreciated. 

Rome 4 nights > Florence - Looks like a 1.5 hour train trip. Or should I go vie San Martino for the scenery?

Florence 5 nights with Day trips to Siena and Bologna > Pisa then Monterosso - looks like about an hour to Pisa then another 1.5 hours to Monterosso..

Monterosso 1 night > Milan - looks like about 4 hours so if I can find a train that leaves Monterosso at early afternoon I can have a bit more of a look around  and still get to Milan by dinner time. 

Milan 1 night > Brig>Chur>Tirano> Varenna - This is what I am unsure of. It looks like this is a lengthy trip so I may need an overnight somewhere, or do I have it wrong? If so, I can take a night off one of the other destinations, but where would be best?

Varenna 4 nights > Venice - looks like about a 4-5 hour trip

Venice 2 nights > Pordenone Looks like a 1.5 hour trip so we could leave Venice after lunch and get to Prodenone by about dinner time.

Pordenone 5 nights with family in Fiume Veneto > Vienna. This is the 8 hour trip you said I may be better of going overnight. 8 hours is a long time on a train if the view is not exceptional. Or is there a way to break it up and make it more interesting?

Vienna 4 nights > Prague - looks like a 4-5 hour trip

Prague 4 nights > Zurich - looks like an 11 hour trip. Might I be better looking for a flight, or is it an interesting journey on the train, or ?????

Zurich 4 days > Basel > Mulhouse > Dijon. From there i was thinking about hiring a car so we could visit the chateaus travelling a path like Givry>Bourges>Loire Valley>Le Mans>Paris. I’d feel much safer going by train, but not sure how to see the sights along the way. Sue’s sister did this drive 10+ years ago and loved it, and we have similar taste. I plan on about 4 nights for the journey. Suggestions welcome.

Paris 4 nights > London - looks like about 2.5 hours

London 5 nights before flying home.   

The loop from Milan, you can just about do it in a day but it would be a full day of traveling. I don't think you'd enjoy the best bit (Bernina Pass) after all that!

Definitely worth spending a night en-route. This will allow you to get off the train and stretch your legs/ explore somewhere.

Maybe take a night off Varenna?

(Edited to add: the connections for that journey from Disentis/Muster to Tirano are at at Reichenau-Tamins and St Moritz.)

It looks like a good itinerary. Plenty of longer stops, giving you time to do day trips.

Monterosso-Milan, I see some Intercity trains taking about 3 hours. These would be the best ones to take. They need a reservation costing €3. They leave at 1255, 1455, 1655, 1855.

Prague-Zurich, I would suggest the sleeper train.

Zurich is a nice city, but I prefer Bern, it's gorgeous. You could explore Zurich after arrival from Prague (if you're not too tired) then head to Bern. Either city is a great base for train trips.
 

You’re a star! Thanks for the guidance. If you think of anything else, please let me know. I am extremely grateful for your kind assistance.

You said “Zurich is a nice city, but I prefer Bern”. In an earlier post you suggested going Zurich > Basel > Mulhouse > Dijon to save on reservation fees.  Would you therefore suggest Zurich > Bern > Basel > Mulhouse > Dijon?

Where the requirement is for a reservation, how far in advance do reservations need to be made?

The key to avoiding/ reducing reservation fees is to make sure you're not on a TGV-Lyria train that's going to Paris.

It's kind of tricky to be specific, as it depends on the time of day and how keen you are to avoid the reservation fee.

For example Bern to Dijon is about 3 hours at it's fastest. Usually with one change, and costing €29 to use the TGV-Lyria. If you leave at the right time of day, you can change at Basel and Mulhouse, and pay €10 or €20 (depending on availability!) for the French TGV.

Or you can get a completely reservation-free itinerary with 2 or 3 changes, taking 4.5 hours at best or 7 hours at worst.

So it's not always clear cut.

For Eurostar and any night trains, do it as soon as you can commit to a date. Night trains are very popular, and there's a limited quota for passholder fares on Eurostar.

For Italian trains, these tend to have plenty of availability, right up to a few minutes before departure. Day before should be fine.

For French domestic TGVs, it's worth booking early if you can. It's €10 until the limited quota is used up, then €20 until the train is full. 

The TGV-Lyria isn't quota limited. It's the same price until the train is sold out.

This is a great resource for finding reservation costs, and how to make them: https://www.seat61.com/interrail-and-eurail-reservations.htm

Vienna-Prague you don't have to make a reservation, but you can get one for a few Euros if you like. 

In the UK, reservations are optional and free (except for sleepers) - regardless of what the Eurail planner tells you. You can make them for all trains on the GWR website.

Thanks again. Next step is to start planning the accommodation. We’ll make the train reservations as we progress through the accommodation at each location. 

A friend of ours, who has been to Europe, suggested that we need to build our fitness now and build some “rest days” into our plan, as we’re likely to get tired after hours of walking. However, now that I look at the travel times, it’s dawned on me that we’re going to spend hours and hours just sitting on a train. We shouldn’t need any rest days - we’ll probably look forward to days of walking. We’re counting on the scenery to fill our other days with awe.  

Your trip looks great ! ralderton gave you great advice already. :)

Just want to add : I wouldn't recommend the full Glacier Express & Bernina loop in a day. First of all you'll very likely miss the 09:23 train as EC trains from Italy are always delayed. And even if you like trains don't spend 10h+ on them (except on a night train of course).

So let's say you take the EC from Milan, start the Alpine journey in Brig at 10:23 and stop for an hour or two along the way (if you want! Feel free to decide on the day) : I wouldn't go further than Chur. Then the following morning :

- Bernina Express Chur - Tirano 08:28 - 12:49 25 CHF extra for the big windows or reservation-free carriages at the front (cab's view)

- R Tirano - Varenna 13:08 - 14:34

Fully recommend the Prague - Zurich night train : one goes via Germany and the other via Austria. The latter is cheaper and more often on-time so choose that one !

Last thing : remember that the train journey is part of the experience, whether a high-speed train in Italy or a (very) slow train through the Alps...

EDIT : I didn't count the pass days but if you were to need an extra one : buy a regular ticket for Rome - Florence -> trains are plenty and so you should find a ticket for about 20€ (bought in advance). That way you save the pass day and the 13€ reservation.

Don't you mean the latter (the one via Austria) is cheaper and more often on time?

Yeah... corrected, my bad

Ok, let me see if I understand this correctly

Day 1 

Take the EC from Milan

Start the Alpine journey in Brig at 10:23 and stop for an hour or two along the way

Overnight at Chur.

Day 2:

Bernina Express Chur - Tirano 08:28 - 12:49 25

- R Tirano - Varenna 13:08 - 14:34

Do I understand correctly? Are you recommending that I miss Andermatt and/or Disentis/Munstr as recommended on the screen print provided earlier? I suspect that even if I miss a leg or two of what’s available, I will still experience an amazing trip!

Also, is it worth paying the CHF extra for the big windows or are reservation-free carriages at the front (cab's view) going to be adequate? I don't want to have regrets over a few dollars, but the exchange rate AUD/EU is really poor at the moment so I need to be sensible.

Thanks for the tip about the overnight train, the train ride Rome to Florence, and your reminder about the rail travel being part of the experience. This is going to be a real change for me. It will be the first time I have ever gone on a holiday and not done all the driving myself. I love driving so I know I will miss it, but it will be good to be able to look around and enjoy the sights, without having to concentrate on the roads the whole way.

You won't miss Andermatt or Disentis/Mustér, they're along the way (have a look at a map if you're unsure) ! I was exactly thinking of those for stops :)

A few years ago I payed the fee to go to the panorama carriages : they were very full and especially noisy. Once I learnt I could see the cab I switched carriages (at a station because you can't cross between the panorama carriages and the leading unit otherwise). I was alone in the 12 seats 1st class area at the front ! You can see the cab and open the windows to get some fresh air and good pictures too.

Now it might have changed a bit because they didn't advertise the front unit as being reservation-free back then but I wouldn't worry about the train being full.

Yes, if you break the journey into two days, you have much more flexibility over the trains you take. 

For one thing, there’s no need to get such an early departure from Milan. You could take the 0820.

i suggest you use my screenshot as a guide, and search for the same places, but pick times that suit you. Remember, apart from that first EuroCity, the rest don’t need reservations. You can jump off the train at any stop that takes your fancy, and spend 30 minutes or an hour there.

Just make sure the planner not trying to send you via Zurich (which it does for some journeys because that’s quicker)

I agree, I wouldn’t pay the reservation fee for the panorama coach. The regular coaches are very high quality, with good windows too. And as @thibcabe says, probably less busy!

Ok, I think I am getting it

Day 1 

Take the EC from Milan

Start the Alpine journey in Brig at 10:23 and stop for an hour or two along the way

Andrematt

Disentis/Munstr

Overnight at Chur.

Day 2:

Bernina Express Chur - Tirano 08:28 - 12:49 25

- R Tirano - Varenna 13:08 - 14:34

It does mean, however, that I either have to take my luggage with me on the trip, making it hard to stop along the way, or I have to go Tirano to Varenna via Milan to get my luggage, as was suggested earlier.

Sounds like I am going to get better photos from the reservation free carriages because I can open the window anyway.

Thanks again

Depending on how much luggage you have, could you leave one bag at your hotel in Milan, and just take enough for the few days of this mini trip?

You’ll be coming back to Milan after varenna to get your Venice train. 

One ‘easy’ stop here is at Alp Grüm on the Bernina Express.

The train is scheduled to stop for about 15 minutes. You can leave your bags on the train and take in the views, have a coffee at the station cafe. It’s very picturesque. 
 

https://www.seat61.com/trains-and-routes/bernina-express.htm

I think that’s about my trip, wrapped and tied up with a bow. I’ll make the bookings/reservations up to Dijon then do some more research as to whether I can confidently hire a car from Dijon to the outskirts of Paris. 

Thanks to both of you for your patience and kind assistance. I really appreciate it.