Our First 'Hiccup'
When Plans Go Sideways
This weekend, we hit our first real challenge complication. We completed 4 of our planned 5 destinations and learned why buffer time and backup plans matter.

We started our FLL (Fort Lauderdale) to RDU (Raleigh), then continued to SJU (San Juan). Everything went smoothly until Puerto Rico. The plan was SJU to EWR (Newark), then train to JFK and the TWA hotel. However, our return aircraft had a mechanical issue.

With a 7 AM flight from JFK to BUF (Buffalo) the next morning, the delayed Newark flight wouldn't work. We needed to get back to JFK that night, or our whole weekend would fall apart.
Finding a Solution
Angie spotted a flight from SJU to JFK that was in final boarding—doors closing, last calls. We sprinted across the terminal to that gate and found a long line of passengers with the same idea.
JetBlue's customer service saved us. Instead of joining the standby queue, we went to the "Ask Me" desk. The agent, Luis Alberto Ortiz Burgos, was incredibly helpful. The flight was sold out with a long standby list, but he somehow got us the last 2 seats.
We mentioned the 25 for 25 Challenge, which might have helped—we're not sure. But it worked. What could have ended our challenge became just a route change.
The Result
We landed at JFK before our original EWR flight even departed. We once again stayed at the TWA Hotel and caught our 7:30 AM flight to BUF (Buffalo) the next morning.
Key lessons: when faced with a mechanical, check the departures board immediately for alternatives; ask agents for help when plans change; mention your challenge (it might help), and stay flexible. Sometimes your solution is literally boarding as you're figuring out Plan B.
The BUF turn was simple—off one flight, one gate over, onto the next flight back to JFK.
The only disappointment at BUF was seeing the Anchor Bar across from our gate with no time to stop. Buffalo wings at 9 AM probably weren't necessary anyway! For reference, the original Anchor Bar in downtown Buffalo is where chicken wings originated. You can read their story here.
We had secured a late checkout at the TWA Hotel, so after landing back at JFK, we walked back to our room to nap and wait for our 3 PM flight to PIT.
In Pittsburgh, we spent quality time with our eldest daughter, a PhD candidate at the University. She loves nature and the outdoors, so I found an unique restaurant called Treetops Restaurant, located about an hour from the hotel. It's in a park with two Frank Lloyd Wright homes, and you eat dinner in your own private treehouse. Great food and service, but the atmosphere made it incredibly special. We got much-needed rest before another early 6 AM flight back to JFK.






Four destinations instead of five, but we learned valuable crisis management lessons for the remaining legs of our journey.





19 done (instead of 20) 6 to go!!
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