A Weekend in Santorini

Santorini (pop. 15,000) is even more beautiful than you’ve imagined, with strange red rock formations rising dramatically out of the sea, whitewashed blue-domed villages precariously perched on the island’s edge, the depressed caldera, a smattering of colorful beaches, those glowing sunsets, and sprawling archaeological sites. If you’re on a honeymoon or romantic getaway—or just exploring solo—here’s how to spend a weekend in Santorini:

Santorini
Stunning views in Santorini © Desislava Vasileva | Dreamstime.com

Day One

There are a few moments in life worth splurging on, and getting a room in Oia or Imerovigli with a view of the caldera is one of them. An entire day can (should) be spent lounging poolside and marveling at the view, but when you feel the need to stretch your legs:

Go for a walk in Oia. Surrounded by water on the northwestern tip of Santorini, Oia lives up to the hype. This might be one of the most beautiful villages in the world. The whitewashed houses carved into the red caldera, the sparkling blue hotel pools, and the tiny alleyways snaking through the village make for a truly unique place. If you need to escape the sun for a while, stop in the Kyrkos Art Gallery or the Musical Instrument Museum, where the friendly owner speaks English.

Head out on one of the most beautiful walks around Fira, the 600-step descent to the small port of Fira Skala. As you walk down the steps, the sea is laid out before you, with little fishing boats bobbing in the water; to your back is the caldera. There are signs pointing the way. Getting back up is more challenging. For those who would rather skip the workout, hop on the Santorini Cable Car, which scales the side of the island every 20 minutes. There are also donkeys that you can ride up, but the donkeys are suffering from carting a never-ending cycle of tourists, so give the donkeys a break and take the cable car.

Have dinner in Fira at the eccentric Koukoumavlos, one of the longest-lasting restaurants on Santorini and famous for its wildly creative dishes prepared by self-taught chef Nikos Pouliasis. This is one of the rare restaurants where the celebrity chef is actually in the kitchen. After identifying about 70 ingredients, we stopped counting. Dishes that seemed like they would never work—turkey with kumquats and a peanut butter chocolate lollipop, for instance—are deliciously executed. Come with an open mind and book the €74 tasting menu—an excellent value. Reservations are required.

Day Two

An early morning can be spent quietly walking around Oia, before driving to the island’s center to visit archaeological ruins, visit some of Santorini’s finest wineries, and catch the sunset from a Venetian castle.

Wake up early in the morning to stroll through Oia. This is the best time to see Santorini’s jewel: before the crowds have woken up, when the streets are mostly empty and bathed in a soft pink light. After, return to your hotel for breakfast.

Head to Ancient Akrotiri for a walk through Santorini’s answer to Pompeii. At once destroyed and preserved by a massive volcanic eruption in 1450 BC, Akrotiri is a living reminder of the stunning contribution of the ancient Minoan civilization. The site was only uncovered in 1860, when the volcanic ash was dug out to be used for construction in the Suez Canal. Take your time walking through the streets of the ancient city. There are also guided tours available. You’ll see the crumbled walls of homes and shops, but also some objects— bed frames, pots, tiled floors, windows—that demonstrate just how alive this place was before the volcano erupted.

Stop for lunch at Metaxi Mas in Exo Gonia. Located inside an old house (you can either sit on the terrace, with a view of Anafi island, or inside the vaulted rooms), Metaxi Mas is a delicious mix of Cretan and Santorini dishes. Dakos (Greek bruschetta), boiled wild greens, and raki are served alongside fava puree and white eggplants. Portions are copious, especially the salads, and though the mains tend toward the meat, there are plenty of vegetarian options.

Fortified, visit at least two of the area’s wineries, starting with Artemis Karamolegos. This is the place to try the sweet, lipsmackingly good vinsanto wine, a dessert variety native to Santorini. At Karamolegos, you can try a vinsanto that has been aged for 60 months! Make sure to also sample assyrtiko, a white Greek wine grape indigenous to Santorini.

If you’re looking to find a side of Santorini that hasn’t been completely dominated by tourism, drive up to nearby Pyrgos for an evening stroll. The former capital of Santorini, Pyrgos is probably the best preserved medieval settlement on the island. Though it’s becoming more of a tourist destination, Pyrgos is still under the radar and doesn’t draw nearly the same crowds as Fira and Oia. It’s a joy to walk through the village alleyways, stop in a platea (village square) for a cup of coffee and some people watching, and to see actual Santorini locals go about their business. Pyrgos is perched on a hill, and the view is just as spectacular as Oia. (Be sure to catch the sunset from the top of the village at Pyrgos Kastelli!)

Thanks in part to efforts by locals to revamp the cultural and culinary offerings in their town, a number of excellent restaurants have opened up here, including the award-winning Selene, where you should stop for dinner. There are two sections: a “meze and wine” bistro downstairs and a fine dining section upstairs, both located in a charming old house. Unless you’re celebrating something very special, the bistro—which has the same views, and an equally impressive menu—is a good (and more affordable) choice. Dishes in the fine dining restaurant include “tomato in a can” (about 5 different tastes of Santorini tomatoes), roasted pigeon, and fava foam on a “seabed.” At the wine bar, try the grilled octopus with fava and smoked tuna.


Start planning your adventure today.



Pin it for Later

santorini itinerary pinterest graphic