Rail Planner cannot book seat reservations, the app only redirects you elsewhere. You can use the Eurail website but it is sometimes more expensive and adds 2€ booking fee per person.
For the first 2 journeys you can use ÖBB or DB. The former offers free 1st class reservations but without seat selection, however as long as you buy together you'll sit next to each other. :)
The way to book is to go to tickets.oebb.at : add Interrail/Eurail as a discount and select one-way tickets. You won't have to enter payment details. There are no booking fees.
The connection in Cologne is a bit tight but since the EC is often delayed, it probably won't be an issue. Worst case : you have more trains either along the Rhine Gorge or via the high-speed railway and all will have plenty of seats in 1st class (optional reservations, free in any case through ÖBB).
EC trains between Switzerland and Italy require seat reservations but the journey can easily be done reservation-free :
- any train to Lugano incl. EC
- hourly RE Lugano - Milano Centrale
Seat reservations are not a thing in Switzerland.
The IC to Ventimiglia and all other trains in Italy can be bought through ÖBB : 3€ per person.
Do not hesitate for further questions and have a look at these 2 links :
https://www.seat61.com/interrail-and-eurail-reservations.htm
https://community.eurail.com/train-connections-reservations-47/how-to-get-reservations-105
As you have a 1st class pass, you will get any optional reservations for free if you make the reservations through ÖBB. If you make the reservations through DB, you pay 5.90 EUR and Interrail/Eurail charges 8 EUR.
To add even further: when making seat reservations via ÖBB you reserve train by train, not the entire journey.
Seat reserving at Deutsche Bahn reserves your entire journey, even when you change trains a couple of times, (all trains needed to get from A to D, with changes in B and C are included in the reservation fee of 5,9 EUR).
When reserving, I usually prefer reserving with the company that runs the trains, as you'll get last-minute updates always sent to you and often can select your seat :)
The recommendation from the experienced travellers in the community is to only make reservations through the Eurail website if no other options are available. Please read more about that below.
Here is some useful information from the experienced travellers in the Community regarding both planning, reservations and activation of pass and travel days.
Planning
The rail planner is normally not up to date, as it only is updated once a month, so to be sure of the time table you better check the timetable and availability on the websites of the national railways. The bigger national railways, like DB (Germany) SBB (Switzerland) and ÖBB (Austria) cover several countries.
Reservations
The advice from the experienced travellers in the community is to use other ways to make reservations than the Interrail/Eurail website. You can look at the guide in the link:
https://community.eurail.com/train-connections-reservations-47/how-to-get-reservations-105
If you, after having looked at the guide, have questions about how to make specific reservation, please give your travel details (departure date, time and route) preferably in a new topic, and you will get advice.
Please note that Interrail/Eurail charges an extra fee of 2 EUR per person and train in addition to the fee for the seat reservation.
Activation of pass
During the activation process you choose the start day of the validity of the pass. Once the validity has started it can't be changed even if you haven't travelled. The advice is therefore to wait with activating the pass and starting the validity until the first day of your travel as you only can deactivate the pass no later than 23.59 CET on the day before the validity starts. If your travel plans change in the last moment you can't deactivate the pass and change the validity.
It can be wise to make a test and activate the pass with a start date well in the future and then deactivate the pass immediately, just to see that everything works.
Activation of travel day
The advice from the experienced travellers in the community is also never to activate a travel day, that is connect a journey to your pass and create the ticket (QR code), until just before boarding the train, otherwise you might loose a travel day if your travel plans change in a late stage You can't delete a travel day in the past. A travel day can only be deleted until 23.59 CET the day before the travel day.
It may also help if you match your use of terminology with the App.
In the App it uses the term TRIP for its diary of your whole use of a pass,whether it be 4 days or 3 Months. As you have done you each create a TRIP for your Pass.
You add to your trip all the individual trains you intend taking. You can add these at any time before boarding - until you transfer a train to your pass this is simply a static diary and trains can be added and removed with no consequence, whether it be minutes, days, weeks or months in the future. (think of when you use your traditional diary to log birthdays or names and addresses. Until you post your birthday card (or transfer to your pass) you have choice.
The term Journey has 2 meanings, one is the complete excursion from start to finish with changes e.g. London to Nice with a change in Paris. The other is a much simpler meaning - a single train from A to B.
I use the second meaning when considering the use of the App as the details for every single train has to be added and activated separately (although the App planner may add several trains from a search for an excursion in one go.) Thinking of them as single train journeys in your diary makes it very easy to change your plans on the fly.
The final word the App uses to note is TICKET. With a mobile pass you effectively create a separate ticket for each train you travel on. When you activate your pass all the trains in your TRIP (diary) will show a grey slider. At some time before boarding you need to operate the slider for the train and it turns yellow. This transfers the train to your pass and, if it is the first of the day, it creates a travel day.
You will then see a new button saying show ticket, which shows a page with a QR code (which has your pass validity details for that day) and below it a list of the train and station details. This is your valid ticket for that train that you present for inspection. If you travel on more trains during that travel day the QR code remains the same but the new train is added to the list below.
As others have posted reservations are completely separate from your pass and, for trains with mandatory reservations, you are expected to have that evidenced separately - usually a pdf on your device or a printed version.
For trains with optional reservations you only need the reservation to find your allocated seat and, if occupied, to convince people to move.
