A Week in Santorini for Our Anniversary

On our first night in Santorini, the power went out across half of Imerovigli just as the sun touched the sea. For about forty minutes there were no terrace lights, no music from the bar below, nothing but the caldera turning from gold to copper to deep blue and the sound of someone, a few balconies over, opening a bottle of wine. Ava squeezed my hand and said, “Well, we couldn’t have planned that.”

We had planned nearly everything else. Ten years married, one week on the most photographed island in Greece, and a spreadsheet that would make an event planner blush. And yet, as usual, the best moments of the trip arrived by accident.

This is our guide to Santorini for couples who want the magic without the elbows: where to stay, where to watch the sunset without the crowds, and the one dinner worth every cent of the splurge.

In this story7 sections

1. Why we chose Imerovigli over Oia
2. Where we'd stay again
3. How we spent the week
4. Sunset without the crowds
5. The dinner worth the splurge
6. Getting there, when to go and what it cost
7. Santorini

Why we chose Imerovigli over Oia

Oia is the village on the postcards, and it’s genuinely lovely. It’s also, between late morning and well after sunset, one of the most crowded places we’ve ever been. Cruise passengers pour in during the day, and by evening the lanes around the old castle ruins are packed shoulder to shoulder with people waiting for the same sunset.

Imerovigli sits higher on the caldera rim, about a mile and a half north of Fira, and it’s sometimes called the balcony of the Aegean. The views are just as dramatic, the sunsets just as good, and the evenings are dramatically calmer. It’s also a short walk from Fira’s restaurants and the bus hub, so we never felt cut off.

We stayed in a small cave suite cut into the cliff, with a private terrace, a plunge pool and a view straight across the caldera to the volcanic islands. It wasn’t cheap: about $480 a night in late September. But we spent hours on that terrace every day, and on an anniversary trip, that’s the room you’re actually paying for.

How we spent the week

We gave ourselves seven nights, which felt luxurious and turned out to be just right. Santorini is small, about 30 square miles, but trying to see it in two days is how people end up spending their trip in a queue. Our week had a loose rhythm: a mid-morning adventure, a long lunch, an afternoon nap, and the sunset as the evening’s only fixed appointment.

The caldera hike from Fira to Oia

Our favorite day by far. The path along the rim runs about six miles (10 km) from Fira through Firostefani and Imerovigli to Oia, with several steep climbs and almost no shade. We started at 7:30 a.m. to beat the heat, stopped for a frappé in Imerovigli, and reached Oia before the cruise crowds. Around Skaros Rock, the old castle headland below Imerovigli, we didn’t see another person for twenty minutes. Allow three to four hours with photo stops, bring at least a liter of water each and wear proper shoes. The bus back to Fira is cheap and frequent.

Akrotiri and the south

The excavated Bronze Age town at Akrotiri, buried by an eruption around 3,600 years ago, is one of the most impressive archaeological sites we’ve seen anywhere. The multi-story buildings are protected under a vast roof, so it’s a perfect midday visit. Afterward, we swam at the black sand beach at Perissa and ate grilled octopus with our feet nearly in the water.

Pyrgos and the wineries

Pyrgos is a medieval hilltop village in the middle of the island, all narrow lanes and church bells, and almost empty in the late afternoon. Nearby, several family wineries offer tastings of Assyrtiko, the island’s mineral white grown in vines coiled low into basket shapes against the wind. A tasting and a cheese plate at sunset cost about $45 each.

Sunset without the crowds

Here’s the honest truth: the Oia castle sunset is beautiful, but you’ll watch it over a sea of raised phones. We tried it once, for the story, and then spent the rest of the week finding better options.

• From a boat. Our sunset catamaran cruise was the single best evening of the trip. We swam in the warm springs near the volcano, snorkeled off the Red Beach, ate dinner on deck and watched the sun go down from the water with the whole caldera glowing above us. Small-group cruises run roughly $150 to $220 per person.
• Pyrgos. The view from the top of the village looks west across the whole island to the sea. A handful of people, a lot of quiet.
• Your own terrace. On our anniversary night, we skipped the crowds entirely, ordered a mezze plate and a bottle of Assyrtiko to the room, and watched it from the plunge pool.

We’d planned the week to the hour, and the sunset we’ll remember forever happened during a blackout.

Noah Parker

The dinner worth the splurge

For our actual anniversary, we booked a table at a fine-dining restaurant on the caldera edge in Imerovigli, two weeks in advance, for the earliest seating so we’d be at the table as the sun went down. We chose the tasting menu: seven small courses built around Cycladic ingredients like fava, capers, cherry tomatoes and local fish, each paired with a Santorini wine.

It came to about $420 for two with the wine pairing and tip, which is more than we’d normally spend on a month of groceries. It was worth every cent. Not because each plate was perfect, though most were, but because for three hours nothing was asked of us except to sit next to each other and watch the light go.

Getting there, when to go and what it cost

There are seasonal nonstop flights to Athens from several US hubs, including New York, Newark, Chicago and Philadelphia. From Athens, it’s a 45-minute flight to Santorini or a ferry from Piraeus, which takes about five hours on a high-speed boat and up to eight on a conventional one. We took the plane in and the ferry out, and the slow ferry through the Cyclades was a lovely way to say goodbye.

Our timing, the last week of September, was close to perfect: sea temperatures still in the mid-70s °F (about 24 °C), sunny days in the upper 70s and noticeably thinner crowds than in July and August. Late May and early June are also wonderful. From November to March, many hotels and restaurants close.

All in, our week cost about $6,200 for two, not counting flights from the US: roughly $3,360 for the suite, $1,300 for food and wine, $520 for the cruise, winery visits and Akrotiri, $420 for the anniversary dinner and the rest for transport and the climate fee.

On our last evening, we walked back to the same spot where we’d watched that first blackout sunset. The lights stayed on this time. It was still beautiful, and a little less magical, which felt exactly right. Ten years in, we’ve learned the best things aren’t the ones you plan to the hour. They’re the ones you leave room for.