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.
Location, location, location – this unassuming inn has it in excess. If a picture’s worth a thousand words, consider that I was able to snap the above photo from just beyond the terrace of the Captain’s Suite (shown at right), where I spent the night. Charm and authenticity reign as the house, known as Kapetanospito in Greek and built in 1864 for a sea captain and his family, has been designated an example of traditional architecture by the Greek Ministry of Culture. Past owners and current proprietor Tony Mosiman have furnished it with a trove of antiques that include lace-draped canopy beds, oversize armoires, and ornate chandeliers. Vaulted ceilings soar with eye-pleasing curves and wide-planked dark wood floors creak with personality. Gentle dogs Casper and Mary laze about seeming to enjoy the view and paying little heed to the myriad cats darting about the winding cobblestone paths. This is not a gated enclave (there is no pool), but rather a small piece of paradise where Oia’s life and commerce goes on all around you.
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.