Baggage Question

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I am taking the empire builder to Essex and staying in the 441!!! I'm booked in a roomette both ways and would like to take a suitcase with clothes, etc for while I'm in Essex and store that in the luggage rack in my sleeping car. I'd also like to bring a duffel bag for snacks and medication and my laptop bag along with me as well. Are they going to raise a stink for technically three carry-ons?
 
The laptop is not included in the carry on count.

Unofficially, if you can carry it all, you can take it on.
 
Not only do you not have to count your laptop, if your duffel bag is small it may be considered a "purse" and also not be counted.

I usually take a rolling suitcase, a tote bag for snacks and stuff, a bookpack or laptop briefcase, and a very small purse (wallet on a strap). Only my rolling suitcase actually counts as luggage for the 2-bag limit, and no one's ever questioned me about it.
 
Brent and I board with the following and have never been hassled:

Two suitcases (one carry-on, one slightly-bigger-than-carry-on-depending-on-the-airline/aircraft)

Backpack (school-size)

Laptop bag

Messenger bag

Purse

Bag of snacks/drinks from CVS

Pillow (I'm picky about pillows, and my allergies are so bad that I really can't take a chance on strange detergent/pillow stuffing)

We schlep it all ourselves, which is key. I try to compact it as much as possible too. Sometimes I can get the pillow in one of the suitcases, and my purse usually gets tossed into the messenger bag if there's room.
 
The laptop is not included in the carry on count.

Unofficially, if you can carry it all, you can take it on.
I second this. Unless it is outrageously over the limit, if you can carry it on, it stays on.
 
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