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Santorini, Greece: Insider’s Guide

by Christos Stergiou | July 20, 2017

The insider advice on this page is from one of Wendy’s Trusted Travel Experts for Greece: Christos Stergiou of TrueGreece.

Trusted Travel Expert
Christos Stergiou

Christos grew up in Athens and on the island of Patmos, where he helped his family run Petra Hotel & Suites. After a decade in the United States earning an MBA from Stanford Business School and working at a Boston consulting firm, he returned home to found TrueGreece, a boutique travel company catering to those independent, luxury-loving travelers who want to see the country’s highlights and hidden treasures with minimal hassle and through the lens of a real insider. Besides booking chic island hotels, Christos can arrange weeklong sailing trips and villa rentals. He receives rave reviews for his guides, especially the ones who will accompany you to the ruins in Athens, Delphi, and beyond and breathe life into all those ancient stones. And then there’s the on-the-ground staff at TrueGreece to act as your personal concierge—round the clock, in case of emergency—and to help smooth over any last-minute wrinkles (those notoriously unreliable ferries, for one). Christos was also included in Perrin’s People, Wendy’s award-winning list of top travel specialists, which was published annually in Condé Nast Traveler magazine from 2000 to 2013.

Trips have a 3-night minimum and start at $700 per day for two travelers. There is an additional trip-planning fee of $350 per person.

What to See and Do

A village street of Santorini is bright white and blue, with pops of pink bougainvillea flowers

The village streets of Santorini are bright white and blue, with pops of pink bougainvillea flowers. Photo: Shutterstock

Don’t miss
Pyrgos. Once Santorini’s capital, Pyrgos has panoramic views of the island and the sea and a wonderful authentic flavor. It’s also home to more than 30 churches and has the island’s most impressive Greek Orthodox Easter celebrations (visitors welcome!).

Thirasia, a quaint little island a few miles off Santorini’s west coast. The two islands were part of the same landmass until the massive volcanic eruption in the late Bronze Age separated them; when you take a boat to Thirasia (it’s an easy day-trip) you’ll actually be crossing the sea-filled crater. Once there, you’ll see what Santorini was like many years ago: a peaceful island with few permanent inhabitants, donkeys, and some simple taverns, both by the water and up in the village.

Don’t bother
Staying in Fira. It has the largest variety of shopping and dining options on the island, but it’s the most heavily trafficked area of Santorini, and its narrow alleyways easily become congested, especially during the peak months of July and August. Have a meal or two in Fira, but base yourself elsewhere on the island.

Cheap thrill
The prehistoric settlement of Akrotiri should be on every visitor’s list—but rarely is. It’s one of the most important prehistoric settlements in all of Greece and sometimes called the Pompeii of the Aegean, since Akrotiri was buried under massive layers of volcanic ash for thousands of years until excavations starting bringing the settlement back to life. It’s well worth the small price!

Bragging rights
Sharing a glass of Santorini’s signature Assyritkio wine with one of Greece’s leading vintners and learning a few secrets of the trade in the process. Paris Sigalas, a mathematician turned winemaker, experimented with his first bottles in his family’s wine cave on the island. A few decades later and his winery, Domaine Sigalas, has won numerous international awards for its mineral-rich whites. Although wine tastings at Domaine Sigalas are a frequent occurrence, you’ll need to make special arrangements with TrueGreece in advance in order to meet Paris Sigalas.

Where to Stay and Eat

Astra Suites Hotel, Santorini

Astra Suites is one of Santorini’s many great hotels. Photo courtesy of TrueGreece.

Best bang-for-your-buck hotel
The cliffside Astra Suites, one of TrueGreece’s closest affiliates on the island, has always been one of our guests’ favorite places to stay. TrueGreece can pass along specially discounted rates, and thanks to our close relationship with the management, our clients enjoy the best rooms within the category they secure and regularly receive complimentary upgrades (the property offers a variety of room types from studios to private pool suites). Honeymooners are treated to additional amenities in their room or suite.

Restaurant the locals love
Move away from the caldera for Metaxy Mas, a traditional Greek taverna located in Exo Gonia, almost in the center of the island. Come hungry and enjoy Greek dishes and specialties from Santorini and Crete. Some of the house specialties include pomegranate salad, fried feta cheese with honey and sesame, and veal filet in vin santo sauce (vin santo is a traditional Santorini variety of wine).

Must-have dish
Fava with lemon is the traditional recipe all over Santorini. Fava, a puree made from chickpeas, as well as the other Santorini staple, tomato fritters, can be found on appetizer menus in many tavernas and restaurants, but at Selene, in Pyrgos, you can try both in one dish.

Meal worth the splurge
For an upscale dining experience, book a table on the clifftop terrace at Ambrosia in Oia. Or try some fresh fish in one of the tavernas on the water in Ammoudi (the bay below Oia). I always have a tough time choosing from the many wonderful tavernas there. Dimitris Ammoudi, Sunset, and Katina are all fabulous.

Prime picnic spot
The faros (Greek for lighthouse) on the southwestern tip of the island, right next to Akrotiri. While you cannot enter the lighthouse itself, the spot where it is located offers panoramic views of the caldera all the way up to Oia, Nea Kameni, and Thirasia. Come for sunset, perhaps after a day spent on the beaches close by!

Instagram moment
Avoid the crowds that head to Oia each evening in an effort to get that perfect sunset photo. Instead, TrueGreece can organize a private sailing tour that starts in the afternoon and runs until the sun goes down, and includes an excellent meal onboard. Nothing will get in your picture but the sun and the sea!

Contact Christos

Not sure if this is the right person for you? Ask Wendy

Best Time to Go

May. The weather is warm but not hot, and hotel rates are more competitive than during the summer. What’s more, the crowds are thinner in May, which has the added benefit of ensuring the service will also be better (during the hectic summer months, service suffers).

Worst Times to Go

August, when both temperatures and hotel rates are at their peak.

December to March, when most hotels, restaurants and shops are closed. Santorini’s natural beauty may not change throughout the year, but in those winter months, you won’t get to experience the true island atmosphere.

Biggest Rookie Mistake

Never leaving the cliffs of the famous caldera. The four towns on the edge of the caldera—Fira, Firostefani, Oia, Imerovigli—draw most of the visitors, but there’s so much more to see on the island. Head to the lovely, smaller villages of Pyrgos or Megalohori, sample the beaches on the eastern side of the island, or visit one of the local wineries scattered throughout Santorini to learn about the unique way in which wine has been produced on Santorini’s volcanic soil since ancient times.

Tipping Tip

Tipping in Greece is sometimes expected, but it’s never required. It’s seen as a gesture of thanks for prompt and attentive service, and you are the judge of whether it’s warranted, but there are a few guidelines to keep in mind. When you take a taxi, it is usually enough to round up to the next euro. At upscale restaurants, a tip of 10 to 15 percent is standard. At tavernas, it’s customary to leave 2 euros on the table; at a café, from 50 cents to 2 euros. In hotels, luggage handlers usually get 5 euros, and on island hotels, guests typically leave 10 euros per day for maids, servers, and other hotel staff at the end of their stay. Alternatively, for a stay of three or four days, guests might leave 50 euros for all hotel staff to share, while tipping porters separately. As for tour guides, drivers, and boat captains, the tipping protocol can be a little complicated. The staff at TrueGreece can offer detailed guidance!


The hotels recommended were...

Wendy and Jeff Baker | October 24, 2018

Every step of the way was so...

Joel Globus | October 4, 2018

Unequivocal thumbs up

Jerry Smyth | September 21, 2018
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