Discover islands that rest like a string of jewels in the southern Aegean Sea, with medieval castles, walled cities and exquisite beaches en route.

Karpathos: Best for activities
Take a 70-minute flight, or the rather more leisurely 16-hour ferry, from Athens on the Greek mainland.

Constructed centuries ago near the edge of the cliffs, Karpathos’s whitewashed windmills were built to last. The wind rushes along the footpath before them, muting the gentle snapping sound of their sails and of the waves crashing against the cliff face 200 metres below. The island’s western frontier, surrounded by the temperamental Aegean Sea, invokes a sense of awe that only nature can deliver.

Karpathos is small, stretching seven and a half miles in length and a mere two miles at its widest point, yet it manages to squeeze in a great variety of landscapes, making it perfect for outdoor pursuits: world-class surfing beaches, roads with soft hills ideal for cycling, and shimmering, glass-blue water for swimming and snorkelling.

Walkers are particularly enchanted with Karpathos, eager to explore the trails that seem to have unravelled across the island like unruly yarn. Manolis Panagiotou is the head of the island’s Friends of Nature group and leads walks at least once a week. ‘The map shows 155 miles of hiking paths, but there are at least another 155 miles of trails not on the map,’ he says.

Karpathos is well endowed with nature. Shaded olive groves, forested mountains, jagged cliffs and hidden coves make walking an endless treasure hunt. ‘The scenery changes all the time,’ Panagiotou remarks. ‘This is what makes Karpathos different. And it’s rare to meet other people on the trail. It’s a lonely kind of place.’

Despite being nestled between Crete and Rhodes, Karpathos feels far away from everywhere. Its isolated population live just as they have for centuries, seeming half-pleased and half-snubbed at being left out of the hubbub of the neighbouring islands.

Over the years, many of the islanders have flown the coop in search of greater opportunities elsewhere, but recently they’ve begun returning to Karpathos, recognising the beauty and potential of their tiny, windswept homeland.

Manolis moved to the island six years ago. ‘I hadn’t seen such an island before,’ he says. ‘My family have always been occupied with the sea – we’ve been sea captains as far back as my great-greatgrandfather – but when I first came to Karpathos, I was fascinated. The other islands don’t really make a difference to me. But this one, it’s beautiful.’

Where to eat
You won't get any more local than To Helliniko Restaurant, with its extended family atmosphere and menu of Karpathian cheese, stuffed artichokes and roasted goat (mains from £4.50; 00 30 22450 23932).

Where to stay
Perched on the cliffs with views over Kyra Panagia beach, Acropolis Studios has modern and spacious rooms with balconies overlooking the coast and red-domed church below. Delicious home-cooked food is served at the shady terrace restaurant, including seafood dishes and moussaka (doubles from £63, including breakfast; Kyra Panagia; 00 30 22450 23002).

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Rhodes: Best for history
Take a 35-minute flight or a 5-hour ferry from Karpathos, heading northeast across the Aegean Sea. 

Alleyways twist and turn, leading deep into the labyrinth of the walled Old Town of Rhodes. Stone buttresses arch overhead as narrow passageways open on to leafy squares. Medieval mansions stand next to Byzantine chapels, Turkish baths and turreted palaces. All that’s missing are armoured knights galloping past and a Gothic princess crying out from a tower window. The museums are excellent, but the history of this place can be felt in the buildings, squares and streets themselves.

It’s late afternoon. The sun bounces off the stonework to create a golden, almost theatrical light as children play in the square and, one by one, window shutters are opened to let in the cool evening air. As night falls, this seemingly timeless place collides with modern life: a moped judders along the cobbles and speeds around a bend, a fashionable wine bar opens its doors. Music, both live and traditional, rings out along an alleyway, mingling with smells of fresh seafood and exotic herbs emanating from a taverna kitchen.

Periklis Sirimis, alongside his father Basilios, is a painter of traditional Byzantine icons using natural pigments mixed with egg yolk, vinegar, holy water and 24-carat gold. ‘To be a painter you usually copy something from nature,’ says Periklis, ‘but Byzantine artists were afraid to paint the holy people and so we try to paint their spirit instead. We try to make something that’s between here and the sky.’

Their studio, overflowing with colourful, stylised religious icons of every size, is hidden away next to one of the ancient fortification walls. ‘I like that the people who are interested come to see,’ Periklis continues. ‘We don’t need to be like the tourist shops where people are around us all the time. I want to be in a secret place.’ In the ancient, maze-like Old Town, his secrets are guarded well. 

Where to eat
Mandala offers modern Mediterranean dishes, like pasta with red pesto and walnuts, and a well-stocked bar (mains from £9;  

Where to stay: Marco Polo Mansion
The magic of the Old Town has found its way to this restored 15th-century house in the old Turkish quarter. A rustic atmosphere sits comfortably with plush décor and warm colours. Have breakfast in a private garden with views of nearby minarets and the city’s walls. With just a few rooms, preference is given to guests staying at least a week (doubles from £80;

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Kalymnos: Best for life by the sea
Curve around the island of Kos, heading northwest on a 3-hour speedboat trip from Rhodes  

A boat chugs into Pothia harbour, colourful paint peeling from its railings and the taste of salt heavy all around. It’s the perfect vantage point to see the spirit of Kalymnos bursting forth at its most lively. The air is filled with the sounds of fishermen unloading their boats, of dishes banging at the waterside cafés, and of mopeds zipping past at full throttle. Ashore, the colours begin their assault: the deep reds and bright blues of the buildings, the orange of drying octopi, and the brown and stark white of sailing masts piercing the sky.

Sponge diving has been the main industry of Kalymnos since the days of Plato and, at heart, the people here still belong to the sea. They are instantly recognisable as hard-working and downto- earth, ensuring that island life here remains at its most authentic.

Each afternoon, next to Pothia’s harbour, sponge divers haul in their catch. Facing the sea, backs leaning against the dazzling yellow cathedral, they pull the sponges from large nets and lay them to dry with an ease born of incalculable experience.

Many of these sponges find their way into Nikos and Aphrodite Papachatzis’s shop, filled with sponges sized from tiny balls to flutes large enough to lose an arm in. Since the 1980s, the industry has flagged, but Aphrodite believes it is integral to the island’s identity and remains hopeful for its future. ‘There’s no formal training – divers learn from father to son – and you have to go very, very deep. But I hope more young people will go back to the traditional ways.’

Boats are everywhere – from elegant schooners to colourful, bobbing fishing vessels. Swaying with the waves, salty and sun-soaked captains tell tales of Kalymnos and of what lies beneath the big blue.

Where to eat
Using produce from its own land, Harry's Paradise has an eclectic, ever-changing menu featuring wine and garlic-marinated pork, and delicate edible flowers (mains from £5.50;

Where to stay
Set amid a flower garden in laid-back village Myrties, Villa Myrtia has spacious apartments and studios – nothing flashy, just traditional comforts that refuse to compete with amazing views from shaded verandas. The hotel is right next to the sea, looking out to moored fishing boats and the Teledos islet beyond (doubles from £36;

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Leros: Best for slowing down and relaxing
Kalymnos’s chilled-out northeastern neighbour is just 50 minutes away by high-speed ferry. 

 Time goes slower on Leros. As the ferry sidles up into Agia Marina, next to faded fishing boats and dozing taxi drivers, it’s almost possible to feel the mellowness in the warm air. There are no big-hitters – only a couple of museums, a few ruins and a bit of diving. The draw isn’t in the doing; Leros is the ideal location to just ‘be’. Sitting on the edge of the dock is the perfect way to be embraced by the warm sunshine, while the breeze carries the smells of fresh baking, burnt almonds and coffee. Cats stretch and locals wander by, but no-one’s going anywhere fast.

Thanasis Argyroudis runs the Hotel Nefeli on Leros and has lived here for over a decade. He believes the main attraction of the island is its tranquillity. ‘The island is a unique place that gives people a certain serenity. It reminds many people of the way islands used to be in the ’60s and ’70s because Leros didn’t have a lot of tourism growth over the years. The traditional architecture has been preserved, which gives people a feeling that they’re staying in a place that hasn’t been touched by time.’

Narrow roads wind their way between beautiful pastel-hued buildings. Traditional bakeries display temptingly sticky sweets. The 10th-century Pandeli Castle fortress is perched like a sandcastle at the top of town, catching the sunset on its stone walls and promising 360-degree views to those who can bring themselves to leave their patio chair and climb to the top. Beyond the castle, a row of creaking, old-fashioned windmills catch the sea breeze.

By the waterfront, hours can be easily whiled away doing little more than sipping coffee and watching the colourful fishing boats – a prime occupation on Leros. When asked to recommend activities on the island, Thanasis considers for a moment. ‘There are hundreds of walking paths leading to magnificent and beautiful places,’ he says. ‘But really, why do that when you can just walk down a short path and watch a beautiful sunset?’

Where to eat
An artsy little restaurant serving calamari with pesto, Milos is easy to find – it's by the famous watermill of Agia Marina (mains from £5; Agias Marina; 00 30 22470 24894). 

Where to stay
Whitewashed and spacious, there is something entirely comforting about the rooms at Hotel Nefeli. Maybe it’s the villagestyle architecture or the elegant bohemian touches of local art and textiles? Grab yourself a top-floor room and contemplate the answer on the peaceful balcony with views over the flower-filled garden to the sea (doubles from £71;

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Patmos: Best for culture

This Dodecanese spiritual centre is 45 minutes by speedboat from Leros, northwest across the Aegean.

The air is filled with heady plumes of incense, bells are tolling and the gathered devotees begin a chant that echoes under a lavishly decorated ceiling. This is the Monastery of St John, a fortified Orthodox priory perched high on a hill in the Old Town of Hora. Nearby, the nuns at the Holy Monastery of Zoodochos Pigi light hundreds of candles to reveal walls covered in intricate frescoes.

For centuries, Patmos has lured religious travellers, and countless Christian pilgrims still come from all across the world to see the island, considered one of the most sacred sites outside of Jerusalem.

The reason is just down the hill: the Cave of the Apocalypse. It was here that the exiled Saint John of Patmos ensconced himself in 95 AD and wrote the Book of Revelation. In the low ceiling of solid rock is a triple fissure, through which the voice of God is said to have dictated the script.

The islanders of Patmos are a mix of proud locals and long-term expats, most drawn here by a desire to express themselves spiritually – or artistically. Shops selling handmade jewellery, paintings and other crafts line the alleys.

Archmandrite Antipas has led a monastic life here for 24 years, and is not surprised that Patmos continues to draw visitors searching for something sacred. ‘They hope to find positive energy, as young people say nowadays,’ he says.

A large part of the Patmos experience is simply relaxing and enjoying a feeling of peace as evening light bathes the landscape in warm, reverential tones.

Where to eat
Benetos Restaurant features Mediterranean food with a Japanese kick, such as house-cured salmon with wasabi (mains from £5;

Where to stay
Stepping through the door of Archontariki Hotel is a magical experience. It is a world away from the ancient narrow streets of Hora, with five luxurious suites housed within a 400-year-old mansion. The rooms are furnished traditionally with very plush touches. Relaxing under the fruit trees in its tranquil garden is blissful (doubles from £133;

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The article 'The perfect trip: The Dodecanese Islands' was published in partnership with Lonely Planet Magazine.