And we did it! Sam was able to stay in it calmly throughout our outing, from our home to Macy's and back! (Maybe he was dizzy from the motion sickness and thus couldn't be bothered to whine at all!) Lol. Nonetheless, it's really heartwarming to see him finally adapting to something new!
So we decided to make the travel bag his new bed too and it seems like little Sam likes the idea too!

- Greetings from KeY's iPhone!
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