Spetses’ most famous inhabitant had a far less relaxing relationship with the sea. In the harbor in Spetses town, a grand statue of Bouboulina claims pride of place. The female sea captain led the Spetsiot fleet to victory in the 1821 War of Independence and she remains an important symbol of the island’s erstwhile political power. A few yards on, I encountered a more modern Spetsiot legend when I passed a seafront house, battered but still handsome, like its owner, who was sitting on his balcony, barefoot and bare-chested, while his wife shelled beans in the cool of the living room. Demetrios Papadimitriou was a captain, like Bouboulina—except he spent 16 years commanding submarines, not leading revolutionaries. He invited me in and showed me his medals, a photo of the Y-5 Triton submarine he’d been on when it sank in 1942, and a painting of his grandfather’s boat from 1891. "We’ve always been captains, but not anymore," he said. "Now my son owns the Fanari grill, in the square." He smiled. "But he has photos of our boats on the walls."
That evening, I met a real descendant of Bouboulina’s, Christos Orloff, who added four faithful reproductions of his family home to the 1865 original to create the Orloff Resort. Tucked away in a quiet neighborhood just above the Old Harbor, the 22-room boutique hotel is built around a courtyard pool surrounded by ancient olive trees. I drank a glass of Chablis and studied the scene, unable to tell whether this particular olive tree or that clay urn was an ancient or modern addition. That was the point, Orloff told me: to bring a modern sensibility to old Spetses. Admiring the local architecture while drinking imported wine, I had to agree that he had struck the right balance.
At the nearby Tarsanas restaurant, the fagri (white snapper) being served had been caught that day, and I ordered some while watching boatbuilders work at a trade as old as the island, sanding hulls at the boatyards at the end of the Old Harbor. Spetsiots have found so many uses for ships—from fighting for independence to picking up a few truffles; from submarine warfare to searching for the perfect spot to swim. Over the years, they’ve also honed their ability to navigate between modern and traditional pleasures, making the island the kind of place where sandy beaches and truffled pasta go hand in hand and you can leave your cars and cares behind.
Monemvasía means "single entrance," and indeed the only way into Monemvasía town, or the craggy, Gibraltar-like little isle on which it rests, is through a stone archway at the foot of a fortress. Its massive wood-and-iron doors are permanently pushed aside, rotting picturesquely as muscular boys wheel carts of produce, water bottles, and fresh laundry along the cobblestones. Tourists enterprising enough to find and pass through the arch discover a maze of stone cottages straggling down the cliffside to the dark sea below.
Monemvasía island is tiny—a little over a mile long and just 328 yards high—but it is a minor marvel. After splitting from the mainland during an earthquake in A.D. 375, the protected citadel of Monemvasía eventually became the island that time forgot. Its allure is not sun, sea, and nightlife but rather the ability to live, however briefly, in another age. Its architecture has remained virtually unchanged since the days of the Byzantine Empire, when it was a significant trading point, famous for the no-longer-produced wine known as Malmsey in England and Malvasia in Italy and Greece. (Sadly, the grape has died out on Monemvasía, though it is still cultivated on other Greek islands.) There is not one modern building on the island, and virtually no year-round residents; the handful of "locals" who run the inns do so for up to 10 months a year, catering to visitors.
At my inn, Ardamis, an ancient well has been converted into a coffee table in one room; in another, a stone storage pantry is now a steam room; and my suite, No. 16, looks out on a ruined Turkish bath. Over coffee on a mosaic terrace with an expansive view of the sea, the hotel’s owner, Vassilis Ardamis, told me about his predecessors in the 800-year-old house: "The Venetian governor lived here; under the Turks, this is where the courts were—a judge named Ibrahim lived in the house then—and two Byzantine emperors made it their home, in the rooms I share with my wife." Ten members of the government’s Ministry of Archaeology oversee the architectural integrity of the village, ensuring that buildings like Ardamis stick around for another 800 years. Life in a historic setting isn’t always easy—Monemvasía is the opposite of handicapped-accessible, and to find e-mail access or an ATM you have to leave the fortress and take the bus across a causeway to the modern town of Monemvasía on the mainland. (Yes, it’s confusing: not only is the ancient town named for the island but the new settlement across the water is as well. To differentiate, locals often call Monemvasía’s Old Town the Kastro, or "Fortress.") Despite my severe e-mail addiction, for three days I never saw a need to leave the Kastro.