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Excursions: Oia, Santorini

The hillside village of Oia offers one of Greece’s most iconic views

Written and produced by Jenny Bradley Pfeffer

If you’re a fan of travel magazines, you’ve likely seen the images. Impossibly white buildings cling to a steep hillside, contrasting sharply with bright cerulean domes. A venerable windmill overlooks serpentine paths that lead to the water below. 

Oia’s iconic windmill

Golden sunsets illuminate the seemingly endless blue sea. 

This is the village of Oia (pronounced EE-ah)—a sparkling gem on the northern coast of the Greek island of Santorini. 

Its postcard-worthy, whitewashed landscape has long made it a travel mecca for those seeking the perfect romantic getaway.

A small town that lives large, Oia buzzes with tourists (and donkeys, since cars are mostly prohibited). 

And while many visitors spend just a day or two here before departing by sea to Mykonos or Crete, you can easily extend your stay to wander the circuitous walkways—and explore off the beaten path.

Footpaths wind along the village’s steep western slope, offering myriad opportunities for the curious to lose themselves in a labyrinth lined with neoclassical sea captains’ houses (many of which were restored after a devastating earthquake in 1956), whitewashed churches topped with colorful cupolas, and traditional cave houses carved into the cliff face. 

Oia’s siren call is not only its landscape, but also its sunsets. Sunrise and sunset are Oia’s conspirators, revealing the village’s rare beauty. Hours before twilight, tourists scurry to find the perfect perch for nature’s show. And although visitors can discover heart-palpitating views almost anywhere in Oia, many make the trek to the iconic windmill—a thatched-roof sentry at the top of the hill—or to Fort Londsa, which occupies prime real estate on a peninsula jutting out into the caldera, the bay formed by the collapse of the Santorini volcano millennia ago.

You may find, however, that the most spectacular spot to be at sunset is just outside your hotel suite. Lodgings in Oia are as jaw-dropping as you’ll find anywhere, with views that will literally take your breath away. With infinity pools and private balconies overlooking the caldera, you may find it impossible to tear yourself away. 

Two of the town’s most lauded hotels—Katikies and Perivolas—offer luxury (and views) that land them on nearly every travel “best” list. Each possesses its own signature look. Katikies boasts dramatic white architecture and a crisp, minimalist aesthetic. 

Katikies hotel

The stark palette is interrupted only by the perfectly manicured bougainvillea and the blue of its crystalline pool. 

Katikies pool

Suites are nestled into the hillside, stair-stepped one above the other, offering unobstructed views of Oia and the caldera. 

Katikies suite

The service is top shelf, with white-clad staffers maneuvering steep steps with cat-like agility as they effortlessly haul overstuffed luggage and room-service trays brimming with drinks and gourmet treats. 

Perivolas radiates romance. Sensuous curves define the hotel’s architecture. 

Perivolas pool

Serpentine stone walls merge with impeccably white facades. Suites—some with private jacuzzis and terraces overlooking the caldera—are converted 300-year-old cave homes. 

 Perivolas suite

Each is simply decorated, with crisp, white interiors dappled in light and punctuated with shots of fuchsia and lavender, all elegant in their simplicity.

If charming is your cup of tea, look no further than 1864 The Sea Captain’s House. Owned by American-turned-Santorinian Tony Mosiman, this enchanting, four-suite bed-and-breakfast is as alluring as an Oia sunset. 

1864 The Sea Captain’s House

Antiques, wide-plank wood floors, artwork by local artists, and canopy beds draped with sheers offer homey appeal under cross-vaulted ceilings. Mosiman is the consummate host, offering everything from private breakfast on your balcony to myriad spa treatments for road-weary bodies.

If shopping is your pleasure, most of the town’s small shops and boutiques are located on the main footpath off the town square. You’ll find a variety of stores and emporiums here, selling everything from souvenirs to high-end jewelry. Don’t miss Atlantis Books—a 10-year-old literary gem whose cozy, book-lined venue down a set of narrow steps belies its eclectic selection. 

Atlantis Books

For local fare, wander off the main path to The Traditional Shop of Oia. Here, shelves are stocked to overflowing with food of all sorts, such as honey with almonds, capers, and jams—all mouthwatering and locally sourced. 

The Traditional Shop

Jewelry stores are ubiquitous in Santorini. Gold gleams from innumerable shop windows. For something different, visit Bezant for a varied selection that includes traditional pieces along with more modern Greek designs.

Ammoudi

While there’s almost no shopping in Ammoudi—a tiny port located 200-plus steps down from Oia—you won’t regret making the descent. (If steps aren’t your thing, donkeys are available for hire.) 

Steps to Ammoudi

Seafood and friendly faces are plentiful here, and it’s not rare to see love-struck couples whiling away an entire day in one of the handful of tavernas (Dimitris and Katina are favorites), nibbling at fresh fish and sipping local wines, breaking away only for a quick dip in the bay. 

And like most anywhere in Oia, you just can’t beat the view. 

Travel Tips

  • Bring walking shoes with rubber soles. Cars aren’t allowed in much of Oia, and the steep, stone walkways and countless steps weren’t built with flip-flops in mind.
  • Don’t forget the sunscreen and a hat. Even in the off-season, Oia is sunbaked.
  • Plan to explore in the evenings, and even after dark, when the cruise ship crowds thin.
  • Pack your swim gear on every trek. You never know when you might happen upon a hidden swimming hole or beach.

Don’t Leave Without…

  • Buying local delicacies (figs, sundried cherry tomatoes, almonds, honey, and capers) from The Traditional Shop. Ask for Maria.
  • Lunch and a wine tasting at Domaine Sigalas winery
  • A sunset couple’s massage at Caldera Massages Studio (caldera-massages.com)
  • A lazy afternoon feasting on snapper, tomato fritters, and baklava at a taverna in Ammoudi. Katina and Dimitris are favorites. 

Katina Fish Tavern

  • A swim in the crystal-clear water off  the rocks opposite St. Nicholas island. (You can find the path from Ammoudi.)

Ambrosia’s white chocolate mousse

Five Star Greece

Since 2000, when Ileana von Hirsch and Evi Aidonopoulou founded Five Star Greece, they have been the go-to source for personalized, high-end rentals—from luxurious seaside villas with full staffs to crewed yachts chartered for a once-in-a-lifetime trip through the Cyclades. (fivestargreece.com)

Find It: Lodging

Photography: John Bessler