Steven Callas

I arrived in Athens in the late afternoon, greeted by a driver holding a sign with my name just outside customs. The pickup was arranged by my hotel, The Foundry Suites in Psyrri. The building used to be a print shop and has since been converted into a boutique property with twelve suites, original stone walls, and a rooftop garden that looks out over the Acropolis. It was a short walk from Ermou Street and the neighborhoods of Monastiraki and Plaka, which gave me just enough time to settle in before dinner.

That evening, I walked to Taverna tou Psirri, a family-run spot with exposed brick walls, string lights overhead, and a rotating spit of lamb just off the kitchen. I ordered the grilled lamb chops, a horiatiki salad, and a glass of dry red from Nemea. A local couple sitting near me offered suggestions for Santorini, drawing half the island on a napkin before their food arrived. Their advice ended up shaping the best days of the trip.

Ferry to Santorini and Arrival in Oia 

I took the Seajets Worldchampion Jet from Piraeus the next morning in business class, which was quieter and more spacious than expected. The ferry takes around five hours, and by the time we docked in Athinios Port, my driver from Canaves Oia Suites was waiting. The hotel is built into the cliffside of Oia, with cave-style suites that include private plunge pools and uninterrupted views of the caldera. My suite had a sun-drenched terrace, a white marble soaking tub, and a welcome bottle of Assyrtiko chilling in a ceramic wine cooler. 

Dinner that night was at Petra Restaurant, located within the property. The grilled sea bream was served whole, with a side of caper leaves and roasted eggplant, and the sommelier recommended a single-vineyard Assyrtiko from the village of Pyrgos. Watching the sun disappear behind Thirassia Island while the sky changed color by the minute was one of those rare travel moments where you realize you’re exactly where you’re supposed to be.

Hiking the Caldera Trail

The next morning I took the Fira-to-Oia hiking trail, a six-mile route that hugs the edge of the caldera. I started in Fira near Aressana Spa Hotel, grabbing a freddo espresso from Volkan on the Rocks Café before beginning the walk. The early morning light gave the whole island a muted glow, and the route between Firostefani and Imerovigli was quiet, with only the occasional bell from a passing donkey or chapel tower.

I stopped in Imerovigli for a late breakfast at Kapari Wine Restaurant, where the view was nearly 180 degrees of sea and sky. After the food and a bottle of sparkling water, I continued north. Once I rounded Skaros Rock and saw Oia in the distance, the rest of the walk felt like a slow descent into a postcard.

Amoudi Bay and the Spa

I spent the afternoon in Amoudi Bay, reached by walking down the steep steps from Oia. The water is so clear you can see fish even in the deeper sections. Lunch was at Dimitris Ammoudi Taverna, where I had grilled octopus, fava puree, local olives, and warm bread. Most of the tables sit just a few feet from the water.

Later that afternoon I booked a deep tissue massage at the Canaves spa. They use volcanic clay and local botanicals in their treatments. The spa is built directly into the cliffside, and the room was quiet and cool after the heat of the trail and the harbor. The treatment was restorative, not just in a physical sense, but in the way that well-designed travel gives you back more energy than it takes.

Final Reflections

Santorini is often misunderstood. Yes, it’s popular, but with a curated plan and the right pacing, it can feel calm and even quiet. The views are dramatic, the food is fresh and local, and the service at the better hotels is genuinely attentive without being overreaching.