Best of Santorini: Ideal Greece Vacation

Fly into Santorini and meet with your local guide, and travel straight to Oia. It will likely be mid-afternoon, and the sun will be bouncing down on the whitewashed walls with the Aegean Sea stretching out in all of the turquoise splendor. The colors are bright, and likely far more vibrant than the postcards have led you to believe. Check into your hotel and relax, and then venture out to take your first steps through the old town with a map in your hand. As the sun slowly fades, you can watch the show from your hotel terrace as the whitewashed houses reflect the color changes, and the sun dips slowly into the Aegean, creating one of the world’s most famous sunset scenes. You will have a private viewing, just like you do for the next week on this beautiful island.

Start your day slowly and sip your coffee on your terrace as the day begins. Perhaps you will go for a dip in the pool, or maybe you will read a book and feel the light breeze. Santorini is a slow island, and nothing happens quickly, and that is the main appeal. You may still be getting over the flight today, so it may be a good idea not to try anything too energetic. But more importantly, it will be good to settle into the laid-back rhythm of island life.

There is only one experience you will not want to miss today, and that is your treatment at the hotel’s spa. Choose your treatment and feel everything from beyond the island drift away. By evening, you should be walking slower, thinking less, and enjoying that feeling that only an island break can create.

Nothing happens too early on the island, so even a full-day cruise will not require you to set your alarm.  However, it is good to get out in the morning so that you can maximize the hours before the mid-afternoon sun beats down.  Begin in the mid-morning with a luxury small-group catamaran tour taking you all around the island. Stop at a small islet and jump off into the Aegean, and then discover some hot springs, where the water is not quite hot but is both warm and very refreshing. Cruise along the cliffs and find some shade, and then stop beside a tiny beach as the crew cooks up a lush seafood lunch.

Keep cruising in the afternoon as there are places to snorkel, beaches to walk on, and a beautiful place to sunbathe on your private deck. Drinks are included, and a fruit platter is part of the afternoon, as you cruise back around the coast towards Oia. Back in the town, you will probably seek a shaded space, so it is likely to be another sunset back at the hotel. Your hotel provides excellent dining recommendations, and there are plenty of restaurants to try in Oia, along with those in the villages nearby. Your hotel is also home to the oldest restaurant in Oia, where it’s been cooking up traditional food since long before tourists arrived on the island.

After a day on the water, a day on the land, a local historian will take you on a tour of the island’s remarkable history. Akrotiri is still being excavated, with just a tip of the town uncovered so far. Most of it is entombed in the solidified ash of Thera volcano, yet the historian can tell you more about what has been found. Civilization thrived here some 5,000 years ago with houses that were three stories high alongside a sophisticated drainage system. So while you can only glimpse what it once was, there is still a wonderful historical show with frescoes on the walls, ceramic jars, alleyways of multi-tiered stone houses, and evidence of mills and masonry.

When the volcano erupted, everyone had to leave, meaning Santorini was empty and barren for many years. Pyrgos was one of the first Cyclades settlements when people returned. For many years it was the island’s capital, and it is now the least touristic of all Santorini villages. From this hilltop settlement, you can gaze across the island, all the way to Oia. You can walk the mazy medieval alleyways, and the unruffled air brings you back to a time centuries ago. As with Akrotiri, having a local guide is essential, so you can start understanding the stories as well as seeing the sights. Today’s tour will be private, and you can return to Oia late in the afternoon or can choose to dine in Pyrgos before returning.

Vineyards tumble down volcanic island slopes as roots stretch deep into the mineral-rich volcanic terroir. The climate is benign here with grapes thriving in warm temperatures while taking a lot of their moisture from the sea breeze. When Venice ruled Greece, Santorini’s wine became the most famous in the world. It was revered all across Europe and was even spared the Ottoman Turks crackdown on alcohol production in the 16thcentury. The vines are old, most of them the flagship Assyrtiko grape, but also Athiri, Aidani, Mavrotragano, and Mandalieria.

Go tasting at three different vineyards, beginning with a cellar-master that will take you around the farm before you go tasting amid the musty smells of an oak cellar. At another farm, you will taste outside, trying different vintages and some new-world Santorini wines. At the third vineyard, you can eat while pairing wines with local food delicacies. Finish each tasting with a Vinsanto, sweet late-harvest wine in a style that was later popularized in Italy as holy wine labeled vin santoor vino santo. After three vineyards, you will probably drift off to sleep later this afternoon, perhaps on a beach or by your swimming pool.

Take a short boat ride to Nea Kameni, an active volcano that stands less than a mile away from the island. The caldera still bubbles away, and you can sense the power of nature, especially on the 130-meter walk up to its peak. Sulfur vents dot the route, and you smell them as much as you see them, an indication that something powerful lies deep beneath the ground. Take a walk in the morning, when there are fewer people on the volcano and the heat is far more manageable, and then cruise to Fira for lunch at one of the coastal cafes, and then move next to fly around Santorini by helicopter. From the sky, you appreciate the island’s geography and see how the volcanic eruptions have shaped everything. Fly along the cliffs and look down on white and blue villages to compare the red beach and the black beach, such vibrant hues to the sand. You can choose to fly all the way to neighboring Mykonos if you would like, as a helicopter is the easiest and fastest way to reach Santorini’s neighbor for a few hours of exploring somewhere new before the last ferry back to Athinios and the western Santorini coast.

You will wake ready to explore Fira, the iconic village where whitewashed alleyways pass blue church domes. Travel beneath a small house, and then out into the magical views of the Aegean. With every corner you round, you can get even more lost, but that is the fun in Fira and Oia as you explore alongside your guide. Rather than wandering aimlessly, you will be walking in search of the best Fira tavernas, the places where locals continue to dine. Stop for a traditional Greek breakfast at a tiny taverna, where the products are exclusively from the island. Visit two more tavernas in search of the best fava, yellow split beans ground into a food similar to hummus, chlorocheese, and capers.

Leaving Fira, you can then tour the island for its best produce. Stop at a tomato farm and pluck straight from the plant. Visit a microbrewery to try the new breed of Santorini alcohol, before continuing the wine exploration at a vineyard. Return to Fira to a beautiful little restaurant overlooking the water, where dinner is a traditional meze of different dishes. After that, you will need to do some walking, through the hidden alleyways to the beach, or perhaps along the cliffs all the way back to Oia.

Your final full day will be spent with both a boat and a captain at your disposal. You can travel anywhere along the coast, or you may choose to travel further into the Aegean, perhaps using one of the boat’s fishing rods to see what you can bring up. The itinerary is up to you, and the captain will talk you through what is realistic, dependent on what time you start, and the conditions of the waters.

Cruise to Perissa and lay back on the Black Beach, or stop at the Red Beach. Cruise beneath all the villages, passing Fira, Firostefani, and Imerovigli, and then travel past the volcano. Lay anchor in quiet places where you can swim and snorkel in private, toast with fine Santorini wines, and sunbathe on the deck. Return to Oia for your final sunset or watch the sun go down from the deck. You can disembark at any of the villages, meaning you can walk straight into dinner reservations anywhere along the western coast.

Wake to your final morning in Oia and take one last stroll through the mazy streets. Gaze over the waters and visit your favorite local tavern for coffee as your tour ends with a private transfer to the airport.