A day trip to Oia certainly inspires oohs and ahs. But only by sleeping here, in the Greek Islands' most iconic locale, can you really understand the true psyche of the Cycladic islands – the brilliant sunlight, the sensual sunsets, the braying donkeys, the mellifluous church bells, the hushed laughter, the tipsy footsteps, and the silence. Once the cruise ships are gone, this gravity-defying hodgepodge of whitewashed traditional houses, clinging to steep cliffs that tumble down to an ancient caldera filled with the deep blue Aegean, truly becomes one of the most mesmerizing spots on the planet. As a result, it’s chock full of luxury resorts commanding upwards of $700 per night in season. On a recent visit, I opted to think small and stay in an intimate and affordable three-room inn set on one of the town’s most enviable perches: 1864 The Sea Captain’s House.
The spacious Captain’s Suite has a white marble bathroom with a Jacuzzi tub as well as its own private stone courtyard (shown at left), which does lose a bit of privacy as tourists traverse the path just in front of it. Still, enjoying a bottle of local wine here (not alone, thankfully) just before sunset was pretty amazing. Up above, the Sailing and Venetian Suites share an elevated terrace offering panoramic views. There is also a fourth suite, Falling Stars, located steps away in a separate house.
Breakfast – either continental or “Lazy” (served late and with champagne) – is included, depending on the type of rate you reserve. And Mosiman also co-owns two nearby restaurants, both of which are very romantic: 22-table Mediterranean-style Nectar & Ambrosia, located on the path to the famous Oia sunset; and the pricier Ambrosia, which features classic Greek flavors with haute cuisine flare and a terrace with sweeping caldera views. The other perfect accompaniment is the inn’s rooftop Caldera Massage Studio & Spa, featuring cave treatment rooms (you can also have a massage outside on the treatment terrace), a dry sauna, and a Jacuzzi with a view. Believe me when I say that one night was not enough and I am already planning my return visit. Rates range from $249–$302/night through May 31, and $262–$355/night from June though October.