Reservations are required from Chiasso, the border point.
The first train is available on ÖBB*, the second isn't (yet). Check back in a week or two.
*add Interrail/Eurail as a discount and select one-way tickets.
About the Bellinzona - Milan journey : the 09:14 service is due to be operated by a single Astoro train. It could be busy and that train easily feels cramped in my opinion.
If you want to save money (and having more space) I'd suggest this reservation-free itinerary :
- IC21 Bellinzona - Lugano 08:35 - 08:48
- RE Lugano - Milano Centrale 09:02 - 10:17
Thank you so much for sharing the alternative! I hope I can take the 09:14 as anything earlier seems difficult. But I need a reservation here at 09:14 though right? 13€ per öbb
And "ticket not available" means they just aren't open right? I was shocked, thinking they are sold out already! Thank you for the note on that!
The connection in Lugano would be very easy, like anywhere in Switzerland. Don't worry.
Yes 13€ from Bellinzona.
No, they're not sold out (it would be extremely surprising). There are hundreds of seats available on trenitalia.com -> you can't book passholder reservations there though.
Both trains can already be booked on raileurope.com (desktop website only).
I'd go for the train at 8:35 and have a coffee in Milan.