After our Aruba trip, we felt we were able to successfully extend our airplane range to basically anywhere in the Caribbean. But after three consecutive island resort trips with Ethan (of varying levels of success), we decided we wanted to try something a little more adventurous.

With me being sick for much of the Aruba experience, it fell to Ariel to fill most of the days for Jacob and Ethan, and there’s only so much time you can spend at the beach and pool without it getting incredibly repetitive. It’s not that there isn’t anything adventurous to do in Aruba, in fact we had a pretty awesome full day of exploration. But we wanted to do more than just 90% pool and beach on this trip.

So we chose Puerto Rico during the week of Christmas. There were numerous reasons for this. For one, it’s a US territory that I’ve never been to. And now that I finally achieved my previous long term Main Quest goal of reaching all 50 states, I was itching to start crossing some territories off the list as well. There’s also a lot to see in San Juan, and a real-life rainforest to visit as well. So a very different vibe than our last three family trips.

Unfortunately, our flight vibes remained the same, and this travel experience was no pony-ride in May sunshine…

After a horrid experience on the way to Antigua last year, and my own personal hell on the flight to Aruba in August, our rough travel streak continued, as NJ got its first White Christmas in at least 10 years. While it was by no means a major storm, the peak hit right during the 2 hour period around our flight.

Despite there being no indication of a delay — our inbound flight arrived and deplaned on time — I knew were in for a rough time just looking out the window as we moved through Terminal C.

But after just a relatively painless 20 minute delay in boarding, we were on our way…

…to sitting on the tarmac for almost 90 MORE minutes.

The flight itself on its own was fine, although there was some turbulence which may or may not have led to Jacob throwing up in the bathroom. Like a champ though (even though it was his first time), he made it without getting any on himself at all. Ethan was ok for the first half of our time on the plane, but the extra time wasted before takeoff took a major toll as we just… ran out of things to do with him.

He was totally disinterested in taking a nap too, so it was just white-knuckle all the way until bed time.

When the plane landed we went to get out bags… which for some reason were sent to a different terminal despite the United app saying they were on their way as usual.

Ok well, now it was just a matter of picking up the rental car. After hustling our way on to the shuttle and getting the last few seats, we arrived at Europcar (which recently bought out many Fox Rent-A-Car locations in North America). The same Europcar we had a horrid experience with in Iceland? That’s right! Surely we would have better luck this time? Incorrect!

We had to wait over an hour, because the first family there had some issue with their insurance, and refused to pay the $35/day for Europcar’s insurance. They kept trying to call their insurance agent, but lo and behold on Christmas Eve they were having trouble getting someone on the line. Eventually they agreed to pay, but there were still two more people ahead of us. Ariel took the kids the grocery store and had time to go and come back before it was even my turn.

Then… surprise! Sorry but we don’t have the SUV you reserved that you needed to fit all of your family’s bags… So we had to cram two suitcases into the trunk, along with the groceries. My large backpack (that is my suitcase for this trip) went into the passenger seat, along with mine and Jacob’s carry-ons, ensuring I could barely see out the window. Ariel sat in the back, with her carry-on below where Ethan was sitting strapped in his baby seat. And the stroller was on her lap for the ride back.

We get to the AirBnB and the apartment we were staying in had an iron gate in front of the door. After deciphering the method to get the keys out of the lockbox, I found that neither key worked for the gate. There was a latch that when I pulled on, the gate still refused to budge. So we called the host, which to her credit, she answered the phone at about 7:30 pm on Christmas Eve. She kept telling me to just pull on the latch and that gate wasn’t locked. Which I had now done at least a dozen times before calling her!

It turned out there was ANOTHER latch that couldn’t really be seen from the outside, that was on the inside of the gate, where you could attach a padlock. Either she didn’t know this existed or forgot. Either way I finally got the damn gate open and we walked into the 90 degree apartment.

The air conditioning worked, but the main unit in the living room made such a racket we just turned it off. I then had to go get Ethan’s crib (which we had rented but because there was no one to let the delivery person in, they just left it on the ground floor), mattress, and high chair, and drag it up the elevator. Which doesn’t sound so bad, but for some reason this foldable, wooden crib had no wheels. And the building didn’t have a dolly to spare so I had to make two trips and then get the thing set up.

Ethan got to bed, then Jacob. Ariel and I were starving at this point, so she ordered a pizza via Uber Eats. But for some reason the app said we had to pay in cash? And we actually didn’t have enough cash to cover it. So I went to the bank across the street to get some. But then, the order kept resetting to “being prepared” and we figured it wasn’t actually happening anyway. My bank trip then turned into an attempt to forage for food on Christmas Eve at close to 9 pm. Every restaurant I walked into within a 5-10 minute walk was either closed or refused to do takeout for some reason.

So I ended up going to a corner store, which had a small restaurant. They apparently made pizza there, but would I be ok waiting an hour for it to be ready? No, I would not. There were a few boxes of DiGiorno pizzas in their freezer so I texted Ariel to preheat the oven and brought one back.

So yeah… one of the more subpar travel days we’ve ever had. And unlike our adventures getting back from New Zealand, there is no opportunity for a “recovery day” when you have young children.

Our fortunes have improved since our travel day and we’re having a fine time here on the Isla Del Encanto. But this, after my recent solo adventure in the LAX dungeons, after the crazy experience we had getting to Antigua, and Iceland, and Aruba… I’m really starting to wonder if it’s us, or just travel in general that’s gotten nearly unmanageable.