A Guide to Sailing in the Dodecanese Islands, Greece

The ancient ruins of the Lindos Acropolis form a must-see historical site on the island of Rhodes
The ancient ruins of the Lindos Acropolis form a must-see historical site on the island of Rhodes | © Kirk Fisher / Alamy
Photo of Helen Iatrou
15 December 2021
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Sprinkled across the southeastern Aegean, the Dodecanese – whose name means 12 islands – is best known for big-name destinations like Rhodes and Kos. Yet, there are plenty of small, remote isles that render the region a bottomless treasure chest of surprises for sailors. Expect burnished landscapes, secluded anchorages, old-school Greek island life and warm hospitality that together appeal to adventurers with a love for history and culture.

Cruise around the Dodecanese islands in style by chartering a vessel through Dream Yacht Charter. Alternatively, hire one of hundreds of vessels with SamBoat.

What to see and do

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.

The caves of Kalymnos is home to some of the best climbing in Greece | © Andrey Bandurenko / Alamy

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.

Best mooring locations

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.

The harbour at Kos Town is one of the best mooring spots in the region | © Roy Conchie / Alamy

Where to eat and drink

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.

Mavrikos is among the finest eateries in Lindos | © Hackenberg-Photo-Cologne / Alamy

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.

Best charter option

Set off from Rhodes, the group’s largest island, or from Kos, strategically located in the middle. SamBoat has a wide array of sailing yachts available in the Dodecanese both destinations for bareboat or skippered charter, including performance cruiser sailboats and comfy catamarans, and even the odd wooden gulet. Alternatively, book a multi-day sailing holiday with Dream Yacht Charter – a great option for novices.

The distinctive Venetian homes of Chalki town form a classic Dodecanese backdrop | © Roy Conchie / Alamy

Where to get groceries

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.

Key annual sailing events

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 Aegean Regatta is a major event in the Greek sailing calendar | © De Visu / Alamy

Climate and weather

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.

Boats moored off Pedi, a picturesque village on Symi island in the Dodecanese

How to get there

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.

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