Honestly unless they really insist on it I'd avoid the road trip option. For starters that is a lot of driving through some areas which are kind of sparsely populated and the roads are presumably very bad. The interstate system as we know and take for granted is if I remember correctly pretty much gone so that means a lot of crappy highway driving or cruising down pieces of the old interstate. It's less "fun and rambling adventure" more "big, potentially life threatening, hassle". On top of that you've got multiple border crossings that they'll likely want to avoid adding further complications to the route. Basically for anyone but smuggler type characters it may well be a big batch of "out of their element". Gently remind them of this.
The trick is to give them a more attractive answer, have a contact offer to get their gear shiped in by a smuggling outfit like technicolor wings and hook them up with fake sins that will stand up at least once to commercial airflight. Then if you want to make things interesting have something happen ont he flight over just for fun, assasination attempt on someone on the plane, overly paranoid courier, murder mystery at 30,000 feet, whatever.
Alternatively if they end season three in the good graces of a certain powerful megacorp exec they might be willing to arrange a no questions asked cargo flight from Manhattan to Seattle. Triple-A extraterritoriality is a wonderful thing.
