Given all the uncertainties about the world of tomorrow, the best course of action is making the most of today. So when the window opened for another holiday across the pond, we didn’t dither and we didn’t dabble – we bought the whole enchilada.

The boys school holiday provided a 2 week window, an ample canvas but with many aspirations. Having been to the Caribbean at an all-inclusive resort a few years back (and Club Med Florida as well), the idea of sunny resort life was still resonating in our minds – especially being able to celebrate Kai’s birthday together. Then we had the chance to enjoy a proper American Halloween (although cutting our jet lag recovery time into slim margins for error). And lastly, the opportunity to join my brother (and his Penn State fraternity crew) and my Wisconsin/Atlanta family for a big football matchup in Wisconsin was too big to waiver.

Meanwhile, the execution was not without its challenges. Hurricanes were wreaking havoc in the Gulf, airlines were pricing tickets as if it were Christmas (at least the Christmases of a few years back), and Chika had a business trip in London starting after the first week of the holiday.

But for our crew of fearless travelers, there was nothing to deter us from our mission. One Sunday evening on a train bound for Munich the airline fares dipped, and after a few hours we had our planes booked, our Caribbean adventure secured (with refundable frequent flyer tickets and cancelable resort rooms), and a manic deadline to get as much sorted out as possible with the office before leaving (which all got delivered.)

The good news about our travel abroad was that we were able to go as the whole family – Teo didn’t have to charm the ladies guarding the lounge to let us have an extra guest this time and I had someone to share drinks with.

While we were able to have an easy start of the journey (8am house departure), we landed quite late in the USA (with a huge security queue) and arrived at my parents almost 4am Berlin time.

The upside to the late arrival was that we could chip at some of the jet lag we needed to get past and Sunday is the perfect day to relax and chill. But that would have to wait because it was William’s 10th birthday extravaganza in New York City!!!

Our Uber (dad) dropped us to the train where we commuted to NYC. As we had already done the observatory at the Freedom Tower, Chika decided to go running in Central Park, while the boys and I hit Chinatown to hunt for Pokémon cards and get some luxury bubble tea. We met up with the crew at the Black Tap Soho, a carnival of calories featuring an eclectic menu of burgers (I shared a wagu burger with Mike that was delish) and the most insane milkshakes I have ever seen. Even Frankenstein would have been taken aback.

The party ventured on to hit golf balls at Chelsea Piers (I was having nightmarish thoughts of what Teo could do) while our crew strolled up the sunny New York Streets to Penn Station.

Monday then became our rest day, with French Toast, gym/pool, some shopping, and a steaks on the grill dinner.

Tuesday we were off at 7am to Newark Airport to catch our flights to Cancun. On the downside, the lounge passes for mom and dad didn’t work but on the upside we were able to get an upgrade for dad for the flight down. Luckily we were heading for plenty of eating as our airport sushi was pretty weak.

By 3pm we were checking in at the Hilton All-Inclusive. It’s a nice new property quite secluded by a big wetlands — great for a chill few days, but not a launchpad for exploring (pyramids will be visited the next go around). We were taken care of by a great host — Dulce Castro — who has the biggest smile and is incredibly warm and friendly (if you should somehow happen to meet her, say hello from us). We did (as planned) secure a nice upgrade to a connecting sea-view suite, which was great to allow everyone to do their own thing even with the jet lag still lurking. As if fate were complicit, the first activity of the day was a Möet Champange tasting as if they knew Chika was arriving.

The weather was pleasantly unpredictable – we had more sun than clouds even when bad times were predicted. I can happily say that I made it into the ocean 4 days in a row. From our room to the pool/beach was only a few minutes so as soon as the sun showed itself we were in our loungers.

As usual, we tried to make the most out of the eating options. For our dinners, we did Italian the first night, then Mexican, and closed out the last night at the grill restaurant. Thanks to my Hilton AMEX, we had $200 resort credit and freely splurged at the grill with a 40oz porterhouse and grilled lobster. They were so happy, they even comped us a delicious bottle of red wine. As far as the other meals, breakfast was always good – there was always some interesting mexican dishes to spice up the routine. And with lunch, there were always great salads (including ceviches) plus tacos and burgers. One day with Chika and the boys we tried the asian a la carte menu which was also a nice diversion. And last but not least there was an ice cream bar with churros — mom was in heaven.

Probably one of the unplanned highlights was that chess.com was having their convention at the hotel. While we couldn’t get a face to face with the grandmaster Magnus Carlsen, Chika was able to get a whole bunch of schwag from the chess.com people and Kai was able to join in the ongoing games in the lobby.

For Kai’s birthday, they delivered cakes on the eve of his birthday, the day of his birthday, and again at birthday dinner. As the adage stated: let them eat cake.

As the first chapter came to a close, Chika flew back to Europe to catch up with business appointments, mom and dad brought the boys back to the homestead, and I continued on to Wisconsin via Chicago.

Stay tuned for Part 2.