If you are a discerning traveler who delights in an elegant stay, romance-inspiring views, and local gastronomy, but seek a place with a casual vibe, you'll fall in love with Santorini. The Santorini of today is moving from courting the daily onslaught of large ship tour groups to fewer travelers who will stay awhile to appreciate her history, monasteries, unique cuisine, local wine, sensual sunsets, languid dining and sumptuous accommodations.
One of the best months to travel to the island is early May or September in the fall. Hotels and shops will be open for the season but it is not overly hot yet. Cruise ship travel is lighter and subsequently the tiny streets and alleys are not engorged with panting day-tourists vying with the legendary donkeys for the fleeting shade. You might even find a taxi when you need one.
Santorini is a 45-minute hop from Athens via plane; however, the caveat to island hopping by air is that you have to go to Athens for a stop-over and then catch another flight. And since this is Greece, your plane may run late—especially if it’s mid-afternoon—so allow extra time to make connections.
For lodging, the five-star Iconic Santorini, a boutique cave hotel off Gali Square and from the Mantis Collection, is where you simply must drop your bags and stay awhile. Traditional, elegant cave rooms are built into the volcanic rock caldera. Connected by stairs and stone pathways wrapping the hotel, the rooms, spa, pergola restaurant and pool, all have a view of the sea. Everything is bathed in brilliant white-wash contrasting with the noon-day sparkle of the deep blue Mediterranean below.
Iconic Santorini has a casual elegance and level of luxury service so rare that you don't notice it; you just feel relaxed and looked after. The morning starts with fresh-squeezed orange juice and whatever you wish for breakfast, served upon your request on your private patio. If you are lucky, the young, talented native-born chef Konstantinos Avgoulis may provide you some rose petal jam from his home garden along with his heavenly croissants. Dinner at sunset is memorable under the hotel's pergola paired with remarkable Santorini wines.
To find your Santorini, especially if this is your first visit, hire Your Greek Friend (a travel company boasting personalized itineraries), and book a tour day with partners Dimitris and Ruth. Beach trips, boat trips, private visits to the Monastery of Prophet Elias of Thera (Thira) to see the manuscripts, wine tasting, farm visits—they do any type of bespoke excursion and adventure that you want. With easy-going personalities you’ll be calling them “friend” in minutes.
Their local connections and knowledge of hidden Santorini really make the difference in what you get to experience while there. As for the clever business name, it was inspired by a visit with a friend who took the day off work to share the best spots and things they like. If you’re looking to delve more into Greek culture, Immersion Classes are offered at Hellenic Culture Center. Programs include language crash courses, art, poetry, music, singing and cooking classes.
Santorini will surprise you with the smallest, most flavorful fruits and vegetables. Due to the lack of water here, once a plant is established, it is on its own to survive. As with the indigenous wine grapes, the little tomatoes have a concentrated flavor. Be sure to try the addictive Santorini Tomatokeftedes (tomato balls) made with fresh tomatoes, onion, mint, flour or farina and Kefalotyri cheese, which is then fried crisp.
One thing you’ll discover is that heritage grape vine stock is trained to curl around itself, forming a basket to protect the fruit and young leaves from strong winds and relentless sun. The secret is in its terrain: no water, extreme sun and wind and lava soils which produces wine with great minerality and character. All the vineyards at Estate Argyros—Assyrtiko, Aidani, Athiri and Mavrotragano—are planted with the indigenous heritage grapes. Look for P.D.O. Designation on the label telling you the wine is completely grown and produced in Santorini. A famous wine mentioned by the Venetians in the 1500s, is called Vin Santo. It is made from sun-dried white grapes, a mix of various indigenous grapes, aged a minimum of four years in oak barrels and up to 20 years for the smoothest ones.
In the village of Pyrgos, Santo Wines offers tours and spectacular views on the shaded terrace overlooking the caldera. A fantastic idea is to sit here with friends and a bottle of the chilled bubbly overlooking the caldera. When it comes to dining in Santorini, you’ll most likely not have a bad meal here. Selene Restaurant has culinary educator Georgia Tsara who is also a sommelier and restaurant manager. She offers an innovative cooking class discussing local products such as fava bean, tomatoes, grapes and capers mixed with influences from Egypt, Turkey, France, Venice, Libya and Persia.
Santorini should be savored. Take your time. Rest when you want, drink what you want, and then allow the magic of her stark beauty to slowly sink into your soul.