Thanks everyone for their feedback! I think I do have Rescue Remedy somewhere and will try it. Fortunately, I think we found a solution. My brother-in-law has agreed to stay at our place while we travel to Rome in May. Jam really likes him and sees him often, and I agree, he will be in his own surroundings and will feel more comfortable.
We're also blessed to have travelled in the car with him as soon as we got him, and he loves it!
Finds it very relaxing and almost always falls asleep! Flying is another thing, we haven't tried that yet
Kind of makes me nervous. So for now, I won't worry about that
I heard that the W chain of hotels is dog-friendly so maybe that's an option in the future. If anyone ever travels to VT, we stayed at a lovely B&B in Manchester called the Reluctant Panther that is dog-friendly and beautiful!