My Life in Ruins
Imagine this: It’s the summer of 2023. You’ve already traveled to Morocco with your family in April, gotten an expensive custom tattoo in May, and, despite your parents' objections, made the questionable financial decision to go to Greece in June. At the time, you saw your adult travel record as 1-2. Costa Rica had been a win — a solid, memorable trip. But the Dominican Republic and Morocco didn’t quite measure up. The DR felt like a bust because you went in November, when the small group made the bad apples too influential. Morocco, on the other hand, had an itinerary that was too focused on culture and history, leaving little room for the fun you’d hoped for.
You were determined that Greece would be different. You thought you had figured it out. The DR’s problem was timing, with too few people and too many conflicting personalities. Morocco’s flaw was an itinerary that left little room for downtime. Greece had what the others didn’t: a bigger group, more laid-back days, and plenty of pool and beach time.
Sadly, you did not in fact have it all figured out. And that’s because your assessment was wrong. Yes itinerary matters. Yes timing matters. Yes understanding what type of traveler you are matters. You knew all of that — scratch that, you planned for all of that.
So why wasn’t Greece magical?
In my Costa Rica movie I defined magic as “the moments that make you feel something.” I still believe that which means by its very nature, you can’t plan for it. Greece might’ve had the ingredients for magic, but that magic never got baked. Despite the large group, many people came with friends or partners, and the few solo travelers I connected with at first eventually drifted off on their own. The activities, though laid-back, were underwhelming— nothing that really left an impression. But the biggest disappointment was how much time was spent on ferries, commuting between the islands, instead of actually exploring them.
This really highlighted the flaw of group trips: they’re designed to cram as much into a short amount of time as possible. In Costa Rica, this worked in our favor. We had the same bus and driver throughout, making the commutes easy and gave us time to bond with our group. But the ferries in Greece required more coordination, which resulted in us leaving places earlier and waiting around longer than if we had a private bus. Consequently, these travel days were a lot longer, more stressful, and didn’t allow for much socializing.
In the end, the trip lacked the right pacing, variety of activities, and group chemistry to make it truly memorable. I didn’t capture much footage, which is a real bummer since one of my favorite things about traveling is documenting the experience so I can relive it and share it later. The big takeaway for me is that the group trip formula might not be right for me anymore. I want more control over the pace of my travels, and I don’t want to leave it to chance when it comes to finding a group that clicks.