I’ve been to Greece’s most photographed island so many times—and each visit represented a completely different chapter in my life.
First time: Early on in my travel writing career, I planned a birthday trip to Santorini with my ex. We broke up before the trip, the first of many breakups; I went anyway, burying myself in the longest Philip Roth novel I could find. It was some compensation that I scored the top suite at Perivolas: a long, whitewashed cave house where my private indoor/outdoor swimming pool was at the foot of the bed. It was like a grotto; after a few strokes I was suddenly outside under the Greek sun, overlooking the Aegean.
Then there was the time I hit Santorini as part of a Holland America cruise on the Nieuw Amsterdam. We were a big group that included my dad and our close family friends. Anticipating that everyone from our ships and all the other cruise ships in port would turn lunch in Oia—the most famous town—into a frenzy, I sprinted to arrange a reservation at Seagull, a restaurant (since closed) with spectacular meze and even more impressive views.
After lunch, my friend Vincent I and were able to coax our parents back towards the ship so we could hike to the other villages that rise above the basin-like caldera. The Grace Hotel—part of the Auberge chain—was new then and it beckoned, so I grabbed an outside table and ordered a bottle of sparkling so we could seamlessly slip into the hotel’s stunning infinity pool. The Grace is in Imerovigli, the highest village—and probably my favorite—which overlooks Skaros rock. The rock is a dramatic sight, like a craggy, flat-topped pyramid with the royal blue sea as a backdrop. We positioned ourselves at the lip of the pool, just staring, mesmerized, and barely caught the last tender back to the ship anchored in the harbor.
But the story behind my above selfie occurred on a later trip, when I was writing about Santorini for Holland America’s brand magazine, Mariner. This was either just before or just after my photographer and I enjoyed a terrific lunch of tzatziki, grilled octopus, and much more at Blue Note in Imerovigli. I was in my happy place, the golden-hour light cooperated, and I was able to capture one of Santorini’s characteristic trios of church bells over my shoulder.
There’s still time to book a Santorini trip this season, but as one of the world’s most enduringly popular—and overtouristed—destinations, try to get there by May, or else wait until September. Even during the pandemic, Greece’s best-known Cycladic islands (Mykonos and Santorini) did good business, and I’m betting this summer will approach pre-covid crowds.