I've taken groups to Santorini several times. Every single time, someone in the group says 'I was worried it would be overrated.' Then they stand on a caldera rim at 8pm watching the sun go into the sea and they stop worrying about that. The island is stunning. The trick is knowing which parts of it to be in.
Stay in Oia or Imerovigli — not Fira
Fira is the main town — hub for transportation, full of tourist shops, loud at night. The caldera views are in Oia and Imerovigli, not Fira. Oia gets the Instagram crowds at sunset but has better hotels and the iconic look. Imerovigli sits higher on the rim and is quieter than both — cave hotels with some of the best caldera views on the island and far fewer tour groups walking past your terrace. I'd choose Imerovigli.
Book a private catamaran for a half day
The caldera looks one way from the cliff. It looks completely different from the water. A private catamaran — not one of the large tour boats — gets your group into coves the big boats can't reach, lets you swim near the volcanic island of Nea Kameni, and puts Oia above you rather than across from you. Book the morning, when the light on the white buildings is softest. This is the experience most people in Santorini skip and spend the rest of the trip wishing they'd done.
Eat in Pyrgos, not Oia
Oia's restaurants are beautiful. The food is frequently mediocre because the views sell themselves and the kitchens don't have to try. Go to Pyrgos — the village at the island's highest point — for dinner. Franco's Wine Bar has one of the better wine lists on Santorini. Metaxy Mas, a 20-minute drive from Oia, serves Greek food that's a level above what you'll find in the caldera villages. Worth the detour.
Visit in May or early September
July and August in Santorini: 35+ degrees, maximum crowds, and Oia's sunset viewpoint so packed you can't see the horizon past the phones in the air. May is warm, the flowers are out, prices are 30-40% lower. Early September: tourists thin out, water is at its warmest. If you have any flexibility with timing, avoid peak summer.
Take the ferry to Naxos for a day
One hour by fast ferry and almost nobody goes there. Naxos is the most fertile island in the Cyclades — its own cheese, its own meat, beaches that rival anything in the Aegean, and a medieval Venetian castle town at its center. A day trip from Santorini shows you what Greek island life looks like when it hasn't been filtered through tourism. One of my favorite day-trip recommendations anywhere in Europe.
Santorini lives up to its reputation — but only if you do it right. That means staying on the caldera rim, skipping the tourist restaurant circuit, and being there in May or September. The island is genuinely beautiful. Just don't let the crowds convince you otherwise.
Written by
Jenn
Founder of Memorable Travel & Adventures. Jenn has personally traveled to every destination in this journal. She plans trips to all of them.
