We’ve all seen it. That iconic postcard with the tiny white stucco houses punctuated with blue domed roofs.
Of course, it’s sunny Santorini, the most visited of all of the Greek Islands and in our opinion, one of the most scenic. Stacked cave houses, infinity edge pools, balconies spilling with hot pink bougainvillea — all perched on the side of a cliff. Santorini is a popular tourist hub with honeymooners and day-tripping cruisers, but far away from the maddening crowds lies a blissfully remote oasis of glistening blue waters and tiny whitewashed villages.
With a little planning, it’s very easy to venture off the well-worn tourist path and experience the remote and authentically charming parts of Santorini that few others do.
Just a quick 30-minute flight from Athens, Santorini is part of the Cyclades Islands and sits in the middle of the Aegean Sea. While the island dates back to the Bronze age (3000-1200 BC), sometime near 1620 BC, one of the world’s largest volcanic eruptions occurred on Santorini, leaving a giant crater where the in its wake. The Caldera (crater rim) runs along the western shore of the island and offers spectacular scenery with its rocky steep cliffs.
The picturesque village of Oia sits perched on the northernmost tip of the Caldera with its steep labyrinth of whitewashed cave houses and tight pedestrian streets. Fira (Thira), the capital of Santorini and home to the bustling sea port, is reached in 15 minutes by car. In between the two sits the sleepy village of Imerovigli, which is our personal pick for an extended stay on the island.
You can easily spend six days on Santorini and never see the same thing twice, unless of course you want to.
Here are our top picks for things not to miss when visiting the spectacular, sun-kissed island.
Sea kayaking
For a adventurous day out on the Aegean, look no further than Santorini Sea Kayak. You’ll paddle by steep cliffs, through crystal blue caves and even picnic and snorkel on a private beach. The visibility is outstanding so keep an eye out for sea creatures and be sure to bring lots of sunscreen and bottled water.
Time travel
Did you know that Santorini is home to ancient ruins that pre-date Pompeii by 2500 years? On the southern tip of the island, you can visit the Akrotiri archaeological site. Initial excavations didn’t occur until 1867, were extensively revisited in 1967 and continue today. To date, only 6% of the ruins have been unearthed and thus far, no human remains have been found.
Tour local wineries
You wouldn’t think that a volcanic island with little foliage, intense summer heat and scant rainfall could produce amazing wines, yet it does. Santorini’s rich volcanic soil provides a natural immunity to phylloxera, which devastated vineyards across Europe in the mid 19th century. The island’s indigenous grape is called Assyrtiko and the vines are trained to grow in low circular wreaths called “koulara”, which over time form baskets protecting the fruit from the elements. Santorini is home to over thirty wineries, so there are plenty to choose from. The most popular winery is Santos, which offers generous tasting menus and sweeping views. For a more intimate experience, book a tour and tasting at the family owned Gavalas Winery or snag a seat at the sleekly styled Estate Argyros.
Travel on Two Wheels
For a truly exhilarating ecofriendly adventure, head out to explore by bike with Santorini eBike Adventures. These guys are the real deal. Vassilis and Katarina are both avid cyclists and know every inch of the island. With them, you’ll see some of the most spectacular panoramas of Santorini. You’ll cycle through a tiny village built strategically to combat pirates, visit a remote chapel that clings to the side of a cliff and stop off at a family owned winery to sample their prized wines (just to scratch the surface)). The eBikes are of the highest quality, so you can work as much or as little as you want. Finish the day at a stunning black sand beach in your own private cabana sipping a cold bottle of Mythos beer. Yiamas!
Hike Skaros Rock
Directly adjacent from Imerovigli sits Skaros Rock. It looks like a mountain with a giant boulder perched atop. In the 13th century, Skaros Rock was fortified by the Byzantine Empire and at its height, consisted of over 200 homes. Today, only the mountain and boulder remain. There is a dirt footpath originating in Imerovigli that leads to the rock. At the top, you’ll discover some of the most spectacular views over the Caldera. There is a small sign to designate the footpath, so keep an eye out. Be sure to wear sturdy shoes and bring sunscreen and water.
Sail at Sunset
Of course, no journey to Santorini would be complete without a sunset sail. Santorini sunsets are touted as some of the best on the planet… and we totally agree. But there are a few things you need to know to make the most of your day. Most of the sailing tours start at the Vlychada port, which is an hour car journey from Oia. Most operators offer free transport from Oia, but it’s a long journey as you’ll also stop in Imerovigli and Fira to pick up fellow travelers. Once you arrive at the port, it is chaotic. Keep in mind, Santorini sunsets are world famous for a reason. Be patient, paradise awaits. From the time you leave Oia until you actually board the sailing vessel, it takes approximately 2.5 hours. But we promise, once you’re on the boat, sit back, relax and enjoy the views. We recommend the Diamond semi-private tour offered by Sunset Oia, which offers an amazing BBQ lunch, complimentary beer and wine, and three swimming stops (including a swim to volcanic hot springs). The tour lasts for approximately 5 hours and ends with a veil of orange and red hues and the shadows of Oia in the backdrop. It is truly breathtaking.
