Romantic and iconic, Santorini is a bucket-list destination for many travelers. But beyond the classic whitewashed villas, there are places where the crowds thin and you can appreciate more facets of this Aegean gem. Watch the sunrise from a secret spot, stay the night in a cave, and more with this list.

Discover Santorini

With multicolored cliffs curving around a volcanic caldera fringed by snow-white houses, Santorini a singular experience. No wonder the island attracts a wealth of visitors in the summer months. Not much here is a secret anymore. That said, you can still blaze your own trail and discover lesser-known gems like little-visited beaches and remote hiking trails. Here are a few of our favorite must-see places and experiences to make your vacation even more memorable.

Also, if you have interest in a combined island holiday, let this nine-day Crete/Santorini itinerary be your guide.

Watch the Sunrise at Oia

Sunrise over the cliffs at Oia

The quintessential Santorini experience is to gaze at warm sunsets from the village of Oia, perched atop the precipice of the caldera cliffs. Each evening the narrow streets, restaurants, and Castle of Saint Nikolas ruins fill with pushy throngs elbowing each other for the best view. You don’t want to miss this iconic sunset. However, know that sunrise is an even more sublime experience. The colors are just as beautiful and you’ll have the whole experience mostly to yourself since many travelers will still be sleeping off the previous night’s ouzo. To enjoy it fully, rise before dawn and head to the castle. You'll be at the westernmost tip of Santorini, and the entire village and caldera will come to life before your eyes.

Stomp Grapes at Megalochori

A chapel in Megalochori

Since Roman times, Santorini has been famous for producing wines made from distinct grapes—Aidini, Assyrtiko, and Athiri for whites, and Mandilaria and Mavrotragano for red. These varietals grow in volcanic soil that lends a hint of Savoie lightness, and one-sixth of this island is given over to wine production. The many independent producers sell their grapes direct to Santo Wines, a cooperative whose Oenotourism Center, directly above the harbor, makes a perfect shore visit for cruise-ship passengers.

For a more intimate experience, follow the "wine route" and discover lesser-known wineries far from the cruise-ship crowd. Head south to Megalochori, a traditional village in the heart of wine country. Start at Boutari Winery, where guided tours in English end with a five-wine tasting. Nearby at Gavalas Winery the owners—heirs to a family tradition dating back four generations—lead their own tours. Try to visit in August, when the Gavalas family welcomes visitors to participate in the traditional foot-stomping of fresh-picked grapes. Finally, head east to Art Space Winery, in the little town of Exo Gonia. Its cave cellars, carved into the pumice rock, double as a museum on the history of winemaking and as art galleries curated by winery owner Antonis Argyros.

Sleep in a Traditional Cave House

A cave home on Santorini

Did you know that Santorinians’ forebears slept in caves? Homes were carved directly inside the island's volcanic rim or on the banks of dry rivers and served to protect against the cold Meltemi winds and the harsh summer heat. But yesterday’s ruggedly functional lodgings are today aesthetically attractive destinations. The tourism boom gave them a new lease on life, aided by a Greek tourism initiative for the Preservation and Development of Traditional Settlements. Many of these structures have been converted into boutique lodgings and are now a part of Santorini’s famed architectural milieu. So, when you’re ready to book your accommodation, add a classically Grecian touch by staying in a “cave.” Rest assured, they're more luxurious than they were millennia ago. 

Get a Tan at Koloumbos Beach

Koloumbos Beach is popular with those looking for privacy

Kamari, Perissa, Perivolos—Santorini’s volcanic black-sand beaches are justifiably popular. But if you’re seeking seclusion, try Koloumbos Beach. Framed by dramatic cliffs and a promontory—Cape Kolumbo—Koloumbos is just 2.5 miles northeast of Oia, near the northern tip of the island. It’s popular with nudists and a good place for your first all-over tan (although the majority of visitors aren’t so bold). Try to go early—by late afternoon, the cliffs shade the beach from the sun. Koloumbos has no beach chairs, umbrellas, or even restaurants (the nearest facilities are at Gia Sas beach bar, half a mile west, which charges exorbitant prices).

Five miles offshore and submerged 30 feet below the water is the active Koloumbo volcanic crater (hence the beach’s name). It last erupted, with devastating consequences, in 1650. Today its hydrothermal vents feed currents that warm the waters off Kolumbos Beach. You can arrive here by quad or taxi—park by Soulis Apartments, from where a trail snakes downhill to the beach.

Visit the Akrotiri Archaeological Site

The remains of a Minoan city at Akrotiri

Now it’s time for some island history. The best place is Akrotiri, an archaeological site where the unearthed remains of a once-buried Minoan city are displayed. This “Pompeii of the Aegean” dates to the 4th millennium BCE and includes an elaborate drainage system. There's also pottery and frescoes adorning the ruins of multi-story buildings buried by the cataclysmic explosion of Thera in the 17th century BCE. The site lies within a modern structure skylit from above. Many of the finest excavated items are displayed at the Archaeological Museum of Thera, in Fira. Combine your visit to Akrotiri with the aptly-named Red Beach, close by.

Stroll the Streets of Pyrgos

Pyrgos' blindingly white streets

Pyrgos, located about five miles southeast of Fira, is among the loveliest and most well preserved of Santorini's small towns. It's also one bypassed by most visitors. Rising among craggy hills near the highest point of the island, it offers sweeping vistas over the famed blue-domed roofs and is a fine spot to enjoy the dawn or sunset. Its labyrinthine lanes abound with myriad churches and other ancient architecture, all blazing magnesium white or painted in cool pastels. The pace of life is more relaxed here, and more traditional, too. Don’t miss the gorgeous Church of Nikolaos Theotokaki, in the heart of the village.

Hike Between Oia and Fira

The trail from Oia to Fira

There are some great hikes on Santorini, but the most memorable is the panoramic clifftop trail that links Oia and Fira. Hiking this eight-mile footpath (2.5-5 hours) will give you a vivid sense of the caldera’s scale and the magnitude of the explosion that created it when Thera erupted some 3,600 years ago. The southern half is paved and walled; the northerly section, beyond Ekklisia Profitis Ilias church, fades to cobblestone and dirt. Set out at sunrise (preferred if you want the trail to yourself) or late afternoon to beat the mid-day heat. Either way, you’re guaranteed sensational photos—way up high, it’s just you and the Meltemi breeze rustling the wild grasses. Take water and sunscreen, and once you arrive in Oia or Fira you can catch a bus or taxi back to your hotel.