OK, I haven’t had such a terrible travel experience in 10 years, but some notes (for those of you who want to avoid the disastrous trip we just went through):
Connections have at least a day layover (especially NYC, Chicago)
Don’t, just don’t. But if you have to then if you are transiting a tough town like New York or Chicago where there is weather (thunderstorms in the summer, snow in the winter, etc.), then take the pain to leave the day before. We didn’t and had a 7 AM to New York arriving at 3 PM with a 9 PM departure to Europe. Long story short, after a mechanical issue, an hour to get paperwork, the crew timing out, we ended up with a general ground stop in New York, so we ended up in Baltimore
Make sure you have *all* the travel applications loaded and keep trying
It is a good thing that I had logins for Hyatt Digital Key, MTA (Long Island Railroad), and NJ Transit, and also could get a Metrocard (for the Skytrain at JFK), Remember, that the time you want this is when you are least likely to need it. In this case, stuck in Baltimore, all the car rentals were booked, and the Amtrak was sold out, but it turns out that you can log in on WiFi on the airplane and try. So having that as an option matters as about 10,000 other people are doing the same thing.
And particularly for trains, keep trying, we found that with Amtrak, it would show as sold out and then not repeatedly over hours. So keep trying. Also, try at the railroad station itself, that can work.
Avoid Race Conditions: Do not use Digital Checkin with Hyatt
Yes, we had the ultimate nightmare of getting a reservation (see above) while on the flight to Amtrak, then the problem is that you can get a reservation, but don’t get a digital key, the problem is that there is a race condition, so when we got there, we had a digital key that opened someone else’s room. It appears that there is no interlock, so the local property can assign a room, and then the corporate system sees it open and overwrites the local property record. A classic problem, so just avoid it!
