Sailing into Symi's amphitheatrical harbour is like drifting into a pastel impression of the picture-perfect Greek island. But there are no sugar cube houses or blue and white clichs: neoclassical mansions in every shade of ochre, umber, and peach line the port and surrounding hills. Jaunty caiques bob between gaudy yachts and elegant gulets decked with Turkish flags. (Turkey's southwest coast is just five nautical miles away).
Although the Ottomans ruled Symi for nearly four centuries, the island enjoyed relative autonomy as a lucrative source of wine, bread, sponges and ships. The Italians, who ruled the Dodecanese from 1912 to 1948, left a more tangible impression on local architecture and culture. Their glamorous descendants still parade along the boardwalk in droves every August. But come off season or venture into the craggy hinterland thick with cypress forests, wild sage and oregano, dotted with hidden monasteries - and you'll have only goats for company.
Where to stay, what to do:
Aliki Hotel, built in 1895, is charmingly retro. 15 rooms are decorated with painted ceilings, family heirlooms, and embroidered bed linen. Amenities are basic and some rooms poky (ask for a sea view), but the old-time ambience and waterfront location are exceptional. There's a secret roof garden where you can see without being seen, and motorboats moored outside, so you can putter off to your own secluded bay.
Villa To PlioMeticulously restored by local architect Dimitris Zographos, this split-level house in the upper town has a walled garden with an outdoor kitchen, and dazzling harbour views.
Panormitis Monastery commands its own bay at the island's southern tip. The elaborate complex contains faded frescoes, Byzantine icons, and a surprisingly good bakery, where the monks serve steaming apple and cheese pies.
Kali Strata (Good Street) has 450-odd steps leading tothe upper town, Chorio - a tangle of cobbled alleys, archways, and crumbling ruins ripe for restoration. At the pinnacle is Symi's ancient acropolis, with vertiginous views of the harbour.
Symi's best beaches are accessible only on foot or by boat. Water taxis service Nanou (white pebbles, translucent water, and a simple taverna under the tamarisk trees); Ayios Yiorgos Disalonas (sheer cliffs, luminous green water); and Marathounda (a sheltered bay with nosy goats and a knock-out taverna, where everything comes straight from the Kalodoukas family's organic farm or fishing boat).
Sorocco - This chic shop beside St John church stocks covetable summer accessories, including featherweight kaftans, paper beach bags, and butter-soft leather sandals.
Tholos (+30 22460 72033) The food is unmistakably Greek at this waterfront taverna, but you won't have tasted anything like it. Try stuffed vine leaves dipped in yoghurt, monk's salad' of bulgar, caper leaves, olives, and caramelised onions, and baby shrimp deep-fried in their shells, a Symiot speciality that tastes best with an ice-cold ouzo.
Trata (+30 22460 71411) is a family-run taverna where the fish is always fresh, the greens aren't over-cooked, service is genuine, and prices are honest.
Tsati, a stylish waterfront bar by the abandoned boatyard, does dangerously good mojitos and margaritas. Cushions are scattered on the jetty, so you dangle your toes in the sea as you watch the moon rise.
Words by Rachel Howard.