No Regrets!

In the fall of 2024, as part of a 50th birthday celebration, Dave, Scott, and I went to Hawaii for 11 days. Great memories, and a realization that these are pretty awesome guys to travel with.

In the fall of 2025, as part of a 50th birthday celebration, Dave and I went to Japan for 18 days. Great memories again, along with a commitment from Dave that we should do this every year.

This is the year I turn 50. With a list of friends ready to join me for some sort of trip to celebrate, all eyes were on me to choose the destination. Where to go?

First thing I needed to address was the return conundrum that stumps any global traveler: do I go back to a place I’ve been that I know is awesome, or do I take a chance with someplace new? I struggled with this one for a while, because I’ve been to so many incredible places that I’d like to return to someday. But I still have a few unseen places on my bucket list. In the end, I decided that since this was going to be my trip, I should go somewhere new.

But where? Among the places on my bucket list were Turkey, Vietnam, and the parts of Argentina, Italy, Portugal, and Spain that I missed on previous visits. I prefer places that are historically interesting, photographically beautiful, and socially fun. After some social disappointments on recent trips, that last one became a priority.

In Hawaii, all the old people and honeymooners retired to their hotel rooms by 9pm, leaving hotel bars and local dives nearly empty and closing early. In Japan, tiny izakayas and a near absence of western-style bars meant the only late-night social scene consisted of kids at dance clubs, a look that didn’t fit Dave or me at all. This year, I was determined to make our destination a place with some real late-night energy.

And where in the world have I not been that is renowned for its late-night energy?

Ibiza.

But wait. I’ve been hearing about Ibiza for decades, and my impression of it has always been that it’s full of raving and puking Brit teenagers. Turns out that is indeed the case, but only in certain parts of the island. There are other parts of Ibiza that are appropriate and fun for a more grown-up crowd, with neighborhoods, beach clubs, and even some of the larger show venues catering to people our age.

That’s good enough for me. I was sold.

Ibiza gave me the anchor, and it was easy to fill things out from there. Barcelona was an easy choice for a return visit, especially with friends who hadn’t experienced it before. And Mallorca, which I’ve never visited but have heard good things about, looked like the perfectly chill finish to a trip like this.

What followed was a scramble to create an itinerary that fit the two-week window Dave and I had for this trip. Enter AI, which did a pretty good job helping to plan the Hawaii trip, an amazing job building the Japan trip, and has since become an indispensable tool for travel planning. It didn’t take long before I had what looked like a pretty perfect itinerary: 4 nights in Barcelona, 5 nights in Ibiza, and 3 nights in Mallorca.

With the skeleton in place, it didn’t take long to put some meat on the bones. The itinerary filled up with cathedrals, monasteries, historical districts, catamarans, beaches, bars, bougie hotels, and dinners at some of the fanciest restaurants in the world. I’d been to Barcelona before, so memories helped plan that part of the trip, while AI took more of the lead on planning the islands.

With the itinerary mostly planned and Dave on board, it was time to survey which other friends might be interested in joining the adventure.

Scott, citing personal obligations, had to bow out early. We’re sorry that he’ll be missing this one, and we’re concerned he might chew up the couch while we’re gone, but we’re confident that he’ll join us on future adventures.

Enter my buddy Matt from Texas, a guy who had been wanting to join me on a trip to celebrate my birthday. He jumped on board early. As excited as he is for this trip, he’s humbled by the travel experience Dave and I share and is willing to let us take the lead. This guy is a real force of nature. All I can tell you is that he will find a way to amplify whatever experience we have on any given day.

Then there was my friend Jerry, formerly from DC but now living a new life in Norway. For Jerry, Spain is a short hop away, but he’s only free to join us for the Barcelona portion. Shame. Despite his lack of true commitment to fun, there’s nothing not to like about Jerry. Just a happy, fun, easygoing guy.

And then there is Tony. He’s Dave’s friend, fresh off a divorce, and ready to let loose a little. Dave vouches for him, so he’s in. He’ll be joining us for bits and pieces of Barcelona and Ibiza.

We’ve got a nice little crew heading out there. The whole thing is already developing a bit of a Hangover vibe.

With the trip planned and booked, the last several months have been spent fine-tuning the itinerary, pouncing on time-released tickets and nearly impossible restaurant reservations, tying up loose ends at work, and shopping. Travel gives me an excuse to spiffy up the wardrobe a little, which is important because I have a habit of wearing fashions several generations after they’ve gone out of style. These periodic travel refreshes are pretty much the only thing keeping me from looking like a complete doofus.

I also picked up a new iPhone with an upgraded camera to properly document all of our late-night adventures.

Then there’s the cultural preparation. Dave told me he’d work on some inappropriate Spanish to improve our social interactions. Matt admitted that he only speaks a little Mexican, so he won’t be much use in Spain.

Yes, we’re going to do our best to offend the entire country while we’re there.

For most of us, the trip begins tomorrow. I’ll be getting on my Lufthansa flight connecting through Frankfurt, Dave will be getting on his Delta flight connecting through Atlanta, and Jerry will be hopping over from Norway, all of us converging in Barcelona within an hour of each other. Matt arrives the following day on his Air Canada flight connecting through Montreal.

¡Vamos!