Yep, we had a bit of a situation on our hands.
After a massive freak out (right on the heels of that morning's sprint), I ended up staying late at the office to see how the heck we forgot to account for this timing snafu. What happened was, we were told of the oath ceremony date 3 weeks ahead, and sometime between getting that notification and the day of the oath, we booked our St. Lucia trip. What we hadn't considered is that when you get your Certificate of Naturalization, you surrender your Green Card. Meaning that the only proof R had of his new status was a piece of paper. A piece of paper that must be handed over when you apply for your passport. And in doing so, he'd be essentially proof-less of his citizenship. That plus the fact that once you become a citizen it is illegal to leave or enter the US on any other passport (making his Italian and Swedish ones irrelevant), meant he couldn't leave the country.
But, praise be that we live in NYC. The land where everything can be head: pierogies at 2AM, a wedding dress tailored in an afternoon, and, most relevant to us, a passport applied for, processed and returned in a day (!). After some Googling and Yelping I found a government agency called the NY Passport Agency. Now when you think of filing bureaucratic paperwork (as sadly, I know all too well), you immediately think of the DMV and the rampant lack of efficiency, right? Well, if Yelp was to be believed, apparently this office (located conveniently near us!) not only processed SAME DAY passports with a smile, they also only charged the ridiculously low sum of $60 for this service.
If you Google "expedited passport service" you'll find a whole slew of shady internet companies that (1) cost upwards of $300; (2) tack on more fees for overnight shipping; and (3) aren't really even done overnight anyway.
So of course I was skeptical, but I sent R over there with a printout of our confirmed travel itinerary, his certificate of naturalization, a passport photo and the passport application. He got there at 12:30PM, took a number, waited less than 10 minutes, handed over his documentation, and was told that since his trip wasn't within the next 7 days, they'd mail him his passport (if it was for a same day flight they would turn it around immediately and for a flight within 7 days it's ready the next day). Regardless of timing it all cost $60.
He came home and two days later a little Express Mail envelope followed him with his beautiful new American passport and his returned Certificate of Naturalization.
Which, likewise, rendered us incredibly grateful, especially given our non-refundable vacation and my non-moveable birthday!