The First Trip I Ever Planned: All Around the Greek Islands at Age 19

Lately I’ve been deep in planning mode for a handful of Greece trips, and it’s had me feeling wildly nostalgic for the very first trip I ever planned: three weeks in Greece with two of my best friends the summer after freshman year of college - a long time ago now, but somehow I pulled it off for under $1,000 each back in the day.

We started in Athens with all the classics: Parthenon, blasting around Plaka, taking our first dips in the Aegean at Kalamaki Beach - then hopped from Crete to Santorini to Naxos to Mykonos, weighed down with backpacks stuffed to the brim (I’ve only slightly improved on this), a stack of ferry tickets, and the kind of enviable confidence that comes with being 19 and blissfully unaware of just how sideways travel can go. The big “sideways” moment came when we missed our overnight ferry, which turned into a last-minute hotel scramble in Piraeus. J got angry, K started crying, and I… snapped into action! Within an hour we had a room, new ferry tickets, and a plan. Honestly, that was the first moment I realized how much I loved this stuff.

The weeks that followed were a blur of Greek yogurt, Greek salads, and grilled octopus for practically every meal. We swam in water so clear I still compare all water to the sea off Santorini, jumped off cliffs, explored the Palace of Knossos in Crete, wandered Naxos’ Old Town, and climbed what felt like a million stairs - up to the Acropolis in Athens, up through Mykonos’ winding Chora, up up up from the little beach in Ammoudi Harbor to Oia Town each day to catch the sunset on the way back to our hotel. Our parents were all thrilled with the detailed itinerary I’d made of where we’d be each day (even if they only heard from us once a week via calling cards).

Now, all these years and trips later, I’ve been creating Greece itineraries that cover those same islands, but with a lot more ferry strategy, a few more luxury hotels, and me still making sure even a missed ferry turns into a smooth pivot. Ever since that first fabulous trip, Greece has been absolutely brimming with memory and magic, whether I’m there in person or mapping it out from my desk.