You need to split your booking in 2 parts on tickets.oebb.at -> add Interrail/Eurail as a discount and select one-way tickets (not seat reservation option, which I guess you've selected). It is counter-intuitive I agree

First Florence - Milan : 10€ seat reservation fee

Then Milan - Lugano : 11€ seat reservation fee for the EC train or reservation-free for the RegioExpress train (not longer).

Let me know if it works (or doesn't)

Btw 29th May is a holiday so plenty people will be travelling but all trains I could see have availability

Edit : Trenitalia won't sell you any seat reservations

The ÖBB website doesn't work very well if you want to book 2 pass reservations at the same time. So if you want to buy a reservation Florence-Milan and one from Milan to Lugano in the same journey, then it will often only offer a reservation for one of the trains. If you then check the trains separately, then they both have availability.

Please note that the fastest connections proposed need reservations of €10 + €11 = €21.

There is also an intercity train Florence-Milan for €3 and there are direct regional express trains from Milan to Lugano that don't need a reservation:

For this connection, you'll only need a €3 reservation from Florence to Milan.

Just an observation : it is funny to note that sometimes the EC takes longer (1h40) between Milan and Lugano than the RE (1h15) !

I believe it is to allow the half-hourly frequency within Switzerland and SBB couldn't get later departure times from Milan so the train needs to sit in Chiasso for a while.

Hi RVDborgt, so if my wife and I want to do the two segments, I need to book four, seat reservations separately? 

Thanks! Your assistance is greatly appreciated!

Scott

So I just tried Florence to Milan for May 29th, one person with discount --it still sees NO TICKET. I’m sure I’m doing something wrong. I also tried for 4th May, same result. I can’t believe that there are no tickets for any train. 

Scott

No reservations for 2-3-4 people will work no problem. It is even better to do them at the same time so you sit together.

It was a question of legs : Florence - Milan, Milan - Lugano instead of Milan - Lugano direct

Does it work ?

Edit : what's the connection you're looking at ? Departure time

After adding the discount, please select one-way tickets (and not seat reservations)

OKAY, I figured it out. I was clicking on seat reservation only--I have to click as if buying a ticket. 

If I book for both my wife and myself, what guarantee is that we can sit together? 

THank you guys!! You’re angels. 

99.9% guarantee, especially as you're booking 2 months in advance

In doubt let us know your seat numbers and we'll have a look (they are not necessarily continuous for some reason)

Yes, you’re right that you can do 2 people at once. Say, why it asks for an extra 4 euros for 1st class but our Eurail Pass is for 1st class. I’m looking at 29 May going Milan Centrale to Lugano. Do you think the regional or any other trains will be booked? Should I skip the reservation. 22 euros total seems hefty for a short ride with a railpass. 

Hi Thibcabe, yeah, I should have booked 2 together but the two seats Florence to Milan are 5D and 13 D. Not a disaster if we can’t sit together for a couple hours. 

High-speed trains usually have mandatory reservations yes. Florence to Milan isn't a short ride for European standards btw : 300 km distance in under 2 hours.

Your Pass is for 2nd class so you can't buy seat reservations for 1st class. They often cost the same but then your pass wouldn't be valid.

- Florence - Milan is 2x10€ yes

- Milan - Lugano is easily done with the hourly RegioExpress train : reservation-free, just hop on and find a seat. (no need to buy 2x11€ reservations for the EC)

Reservations on regional trains are impossible and reservations in Switzerland are a waste of money in general : trains are frequent and have lots of seating. Nobody does them anyway. I've lived here all my life and never bought reservations once, it never occured to me :)

Too bad that you didn't get seats together, you could always gently ask the passengers on-board the train to move if possible.

Edit : Nobody will have reservations on the regional train Milan - Lugano as they're not available ! Simply board the train early and you'll find seats together for sure

I’m all set for my Florence to Milan to Lugano (I’ll board a regional to Lugano) but Thibcabe brings up a point. How does the system know I have a 1st class pass? I had to pay a couple Euros extra on the website and should not have had to if I’m carrying a 1st class pass.

The operators set the reservation fees, while most are the same for 1st and 2nd there is no rule that this is the case and some such as this as well as Eurostar, International TGV and others do have higher reservation fees for 1st class. Norway on the other hand has charges for 2nd class reservations while 1st class are free.

Just to note, those fees are applicable to the seat chosen, a 2nd class pass holder can only choose a 2nd class seat and pay whatever fee applies for this.

A 1st class pass holder can chose either a 1st class or 2nd class seat. The reservation fee applied will be corresponding to the seat class chosen not the class of ticket (pass) held.