Umbrella stroller

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I'll be traveling with my grandson to Orlando from 30th Street station on the Silver Star, will I be able to check the stroller as baggage or will they make me take it in my Roomette?
 
Strollers may be checked as baggage where service is available, and both Philadelphia 30th St. and Orlando offer checked baggage service.
 
I'll be traveling with my grandson to Orlando from 30th Street station on the Silver Star, will I be able to check the stroller as baggage or will they make me take it in my Roomette?
You can choose either. If you really want to check it in, it will count against your baggage limit. I can't really find anything concrete saying it, but I believe that only a paying passenger is entitled to any check-in baggage allowance. So if your grandson is under 2, I don't believe that you'll get a baggage allowance for him. I'm sure that a child on a half fare is allowed the full baggage allowance.

If you bring it onboard, a stroller is considered a baby item and doesn't count towards your carry-on allowance. There's kind of a gray area there if it's for a free infant or for a paying child, but I'm pretty sure they'll let you bring it onboard, even if it's over the carry on size limits. I brought a larger folding stroller for my then 2 year old, and it was just stashed in a section where other larger carry on baggage was stowed. The rules theoretically state that it can only be done for an infant. It doesn't say paying or non-paying since it's possible that an infant may be required to be on a paying child fare since only one is free per accompanying adult.

https://www.amtrak.com/baggage-guidelines-booking

Infant Items

Passengers traveling with infants under the age of two may bring an additional infant item onboard (strollers, diaper bags), which does not count towards the carry-on baggage or personal item limit.
 
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