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And any journey that uses restriction 8A. TfW seem to like using this for Off Peak Returns, which allows travel at any time (like an Anytime Return) but break of journey is not permitted. Cardiff - Swansea is an example.
If it's a digital railcard, you should be able to do all of it online. Create an account on the TfL website, add your payment card/device, add your railcard number (which TfL validate with RDG) and away you go.
I think you mean Esher, which is the station for Sandown Park racecourse, rather than Sandown on the Isle of Wight?
You just need a ticket from Surbiton - Esher and you can travel on a train straight to Esher station.
But is every ticket checked on the train after every stop? It's quite easy to get on a train and ignore the guard when they ask for "tickets from station X". Short of fitting a tracking device to each passenger when they enter a station, people will always find a way to pay less, or not at all...
If you want better value for money, you can always take the stopping services where you'll get to spend twice as long travelling for the same price. Depending on the route, it's either around 67 or 73 min.
It's not practical to do that as you'd need staff at each set of doors to check whether someone is going west of Swansea. There also looks to be a train to be an 08:52 to Great Malvern on the adjacent platform.
"Each car has double-flanged wheels on one side and unflanged wheels on the other—the two cars are a mirror image of one other. This means that at the passing loop, each car is automatically directed to its own side of the loop, whether it is traveling up or down."
Taken from...
Actually, you can't use Oyster to Luton (but you can use contactless) and you can't use Oyster or contactless to London Southend and London Oxford airports.
Santander offer a 4 year railcard with their student account: https://www.santander.co.uk/personal/current-accounts/santander-edge-student-current-account
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