A Guide to Sailing in the Dodecanese Islands, Greece

Cruise around the Greek Islands in style with Culture Trip’s Sailing Trips.

It’s easy to conjure images of knights on horses clip-clopping through the cobblestoned streets of Rhodes’ Unesco-listed Old Town. In Europe’s oldest continuously inhabited medieval settlement, pay a visit to the Palace of the Grand Master, Archaeological Museum of Rhodes, the Church of Our Lady of the Castle and the Decorative Arts Collection with a single (affordable) ticket.

Renowned for its sponge-diving history, Kalymnos is today considered a rock-climbing hub that combines the thrill of scaling a craggy cliff face with views of a glistening Aegean below. There are more than 3,400 limestone routes to choose from, catering to both newbie and experienced climbers.

On deeply spiritual Patmos, you’ll find the Cave of the Apocalypse, where St John the Divine purportedly received visions from Christ and penned the Book of Revelation. The Monastery of St John the Theologian, founded in 1088 by a Byzantine monk, hosts invaluable Orthodox documents and icons.

One of the south Aegean’s most impressive marinas is found on Kos. The municipal-owned facility (VHF channel 77; +30 22420 44150) has 265 berths for vessels up to 80m (262ft), a 12-minute walk from the island’s capital, along with restrooms, showers, a supermarket, café-bar, restaurant and marine supply stores.

Palionisos Bay, on Kalymnos island’s northeastern coast, is a laid-back, isolated anchorage offering good shelter from northerly and westerly winds. Mooring buoys, owned by the two tavernas on the bay, can be reserved in advance (+30 6948 945936 / +30 6948 607612). They’re free, so repay the courtesy with lunch or dinner.

Pirate attacks across the Dodecanese between the 12th and early 16th centuries forced inhabitants to resettle in hilly interiors, where they developed farming skills, rather than relying on the sea for their sustenance.

On Karpathos, local handcrafted pasta makarounes is served with sautéed onions and myzithra cheese. Moukounies, a classic dish from Nisyros, involves pieces of pork cooked in its own fat and flavoured with wild oregano.

In the whitewashed seaside town of Lindos on Rhodes, low-key Mavrikos restaurant melds tradition with experimentation in ingeniously simple dishes like black butter beans with carob honey.

Astypalea is worth visiting if only to dine at Astropelos, where the seafood is the star of the menu. Try the local oysters if available, as well as lobster pasta and fish chargrilled whole.

If you’re departing from Rhodes’ new marina, stock up on baked goods and other essentials at ABC supermarket in the marina complex. At Kos marina, Kostas supermarket offers a provisioning service. Elsewhere, seek out fresh local cheeses, fish, fruit and vegetables at farmers’ markets and shop for meat at local butchers in main towns.

Greece’s most popular sailing race, the week-long Aegean Regatta, is held annually in mid-August. Every second year, the event takes place in the south Aegean, with enthusiastic sport and performance-class yacht crews navigating race legs between large islands like Rhodes and around small isles, such as Lipsi, with rest days allowing exploration of each destination.

The Dodecanese’s southerly location means it has Greece’s warmest weather but also forceful winds in summer. Days are hot and sunny from May through September and, often, well into October. The Aegean’s prevailing summer wind – the meltemi – blows from the northwest in the north of the region and from the west in the south. It can be quite powerful between July and September, reaching Force 7 at times, therefore the area is best suited to sailors with intermediate experience, or skippered boats.

Rhodes and Kos are well connected to a host of cities, including London, Stuttgart, Tel Aviv and Moscow, with daily direct flights to the islands’ international airports in the summer. Alternatively, fly into Athens and take a domestic flight to your final destination. Taxi transfers to Rhodes or Kos marina, from their respective airports, take about 30 minutes.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.