Nobody comes to Agathonisi for a cosmopolitan, luxurious or edge-of-the-seat experience. On this island of around 100 residents near Samos and the Turkish coast, which celebrates the arrival of every ship, vacations consist of the bare minimum: some beaches with sand and tamarisk trees, two small villages and a couple of café-bars where you’ll enjoy tasty food made with local ingredients. Festivals with live music and traditional island dancing occur often. If you’re in the mood for exploring, you can spend some time at the Kastraki archaeological site, where entry is free. -Olga Charami
No direct connection from Piraeus. Local boats or catamarans from Samos (40–90 mins), Patmos (2 hours), Kalymnos (2.5 hours), Rhodes (5 hours) and other Dodecanese islands.
Like seafarers discovering a secret island is exactly how you feel when you disembark on the small pier. Chances are you’ll be getting off your own craft, as this is how most arrive here, but you can get a boat from Samos or Patmos. Having a boat is useful here, as there are few roads. People, too, are scarce; there are only 40 permanent residents. What you will find in abundance are oleasters, olive trees, pine trees, cicadas and simplicity. The two tavernas use local ingredients, especially cheeses and meat. -Olga Charami
No direct connection from Piraeus. Flight to Samos, then catamaran (45 mins). Alternatively, a local boat or catamaran from Patmos (20-50 mins).
This island, known as the Butterfly of the Aegean, does indeed look like one when seen from above. Hora, the main town, is one of the prettiest villages in the Aegean, more like a Cycladic settlement than a place in the Dodecanese. The climb up to the castle takes effort but rewards with views. Astypalea has many beaches, and it’s easy to find that feeling of splendid isolation. Livadi Beach is large and sandy; Kaminakia Beach is better for snorkelers. Vatses is ideal for the sunset, and the islets of Kounoupes and Koutsomyti, accessible by boat, are surrounded by turquoise waters. Pebbled Tzanakia has a view of Hora, where you should head after your swim and grab a table near the landmark Moungos café for some people watching. Here, you’ll see almost everyone on the island stroll by as they head out for dinner or drinks. N.B. Leave some room in your suitcase for a souvenir: a jar of the island’s excellent honey. -Nena Dimitriou
Ferry from Piraeus (7.5-11 hours). Direct flight from Athens.
This satellite of Rhodes is one of those islands that casts a spell even before you get off the boat at the port, which in this case is also the capital, Emborio. The coastal road runs in front of colorful 19th-century townhouses with uniform red-tiled roofs and wooden window frames. There are very few cars in the capital, and car traffic is banned entirely from 18:00 onwards every evening. You can reach the beaches of Pontamos or Ftenagia on foot, or take a tour boat to two-sided Tracheia Beach, where you can decide on which flank of the peninsula’s neck to lay your towel. Make the one-hour trek from the abandoned village of Horio to the medieval castle, on the way to which you can see the ancient thrones of Zeus and Hecate. From the 269-meter summit within the castle walls, you’ll be rewarded with great views of the island and of southern Rhodes. -Nena Dimitriou
From Kamerios Skala on Rhodes (50 mins). Ferry from Piraeus (30 hours).
Beyond the lovely beaches and interesting architecture that characterize Kalymnos, it is its cliffs and rock faces that attract most people to the island. It is, in short, an internationally renowned rock-climbing destination. Hundreds of routes, most of them located around Armeos and Masouri, will keep you busy if you are a climber, or impress you if you’re just visiting. Either way, everyone ends up on a beach for a refreshing dip before indulging in plates of local goat or fresh fish, the latter caught by one of the largest fishing fleets in the Mediterranean. -Olga Charami
Ferry from Piraeus (9-11 hours). Direct flight from Athens.
This island simply won’t let you get bored; it has lovely hiking trails, more than 100 beaches, traditional villages and registered historic settlements that look like illustrations from old books, as well as plenty of summer festivals with live music performed on lyres and Greek bagpipes; you’ll find it hard to resist joining in the fun and mixing with the friendly locals. Make sure you swim in the turquoise waters of Apella or Araki, explore the ruins of Kazarma and visit colorful Olympos, where the local women wear floral headscarves and still use looms and wood-fired ovens. One of the highlights on the island’s calendar of festivals is the celebration at the Church of Ai-Yiannis in the ancient necropolis of Vroukounta (August 28-30). -Nena Dimitriou
Direct flight from Athens. Ferry from Piraeus (20 hours).
The traditions of Kasos are even more moving than its beaches and villages. Time-honored celebrations, vibrant local music and special customs have been preserved, against all odds. Lyres and violins, mantinades (rhyming couplets, often set to music) and special dances are part of impromptu festivities and church fairs. The local cuisine follows a culinary tradition based on old recipes. Try the miniature dolma (stuffed vine leaves), the delicious cheeses, the seafood meze and the homemade pasta. Chances are you’ll be offered one or more of these by the locals, who are generous and welcoming and consider visitors to be their personal guests.-Olga Charami
Flight from Athens, one stop. Ferry from Piraeus (21 hours).
Perched at the easternmost edge of Greece, Kastellorizo is a tiny jewel. Known as Megisti until the Middle Ages, it became Kastellorizo when the Knights of the Order of St John built their castle, “Castello Rosso,” on top of the red rock that rises above the port. Unknown to most people, except for the tens of thousands of Kastellorizian expatriates in Australia and a few Italians who discovered it in the 1970s, the island was introduced to the international public in 1991, thanks to the Oscar-winning film “Mediterraneo.” The minaret of the mosque at the entrance of the port is a reminder of the Turkish occupation, but the colorful neoclassical mansions, the impressive public buildings and the churches bear witnesses to the great wealth that maritime trade brought to the island in the 19th century. Kastellorizo is a color, a dip at the port, elegant accommodation, a walk up to Aghios Georgios tou Vounou (“St George of the Mountain”); it is the peace and tranquility of a swim in the embrace of the Blue Cave. -Maya Tsoclis
Flight from Athens, one stop. Ferry from Piraeus (21 hours). Alternatively, flight to Rhodes, then catamaran or ferry (2.5-5 hours).
Its worldwide fame may be linked to Hippocrates, the father of Western medicine, who was born on the island and taught at the Asklepion here, but Kos has much more than just this connection to offer its visitors. For years, the island excelled at package tourism, but today, thanks to its new airport, the restored central boulevard of Finikes in Kos Town and the constant improvements to the island’s restaurant scene, it attracts individual travelers who do not wear all-inclusive hotel wristbands. The more adventurous of these come for the excellent local wines and other food products, boat excursions, horse riding on the beach and cycling on the 12km network. The rest are more than happy to spend their vacation swimming in the bright blue waters and sunbathing on sandy beaches. -John Papadimitriou
Ferry from Piraeus (9-13 hours). Direct flight from Athens.
Until a few years ago, a close circle of initiates were the only visitors here. The island has been spared all that comes with mass tourism, and with minimal night-life, it retains an air of small-town intimacy. The bay of Aghia Marina is one of the Aegean’s loveliest; it’s lined with old houses in bold tones of ochre, and the settlement is crowned with a Byzantine castle. The fascinating town of Lakki (Portolago), built from scratch by the Italians as a military base, was constructed entirely in the interwar Rationalist style. Mylos, arguably one of the best restaurant in the entire Aegean, lures day-trippers off their yachts – don’t miss it! -Alexandros Massavetas
Ferry fromPiraeus (10 hours). Direct flight from Athens.
For Years it was something of a secret as a holiday destination. But even now that the secret is out, Lipsi remains an island for people who don’t want much more on their vacation than a nice beach with a couple of tamarisk trees and crystal-clear waters. A certain cosmopolitan air has also been noticed in the past few years, as old local houses are being bought up, mainly by Italians. Lipsi is also known for the Fokiano grape, which traveled all the way to the Vatican back in its heyday, so you won’t want for wine, especially as there’s a winery here producing the stuff. It also has a traditional dairy making cheese and other delightful foodie stops. And as for the swimming, your choices are not limited to the island itself: take the regular ferry service out to Aspronissia, two tiny islets with beaches of smooth white stones and clear, turquoise waters. -John Papadimitriou
Ferry from Piraeus (9 hours). Flight to Leros, Kalymnos, Kos or Ikaria, then catamaran (20 mins-2 hours).
How about a hot walk inside the crater of an active volcano, with the strong smell of sulfur wafting about? That’s just one of the surprises that Nisyros has in store for you.The others? There are quiet beaches with black-red sand, the legendary Oasis taverna for meze and parties, raki and nibbles on Ilikiomeni Square in Mandraki, fresh fish in Pali, meatballs on Nikia Square with its pebbled mosaic, a walk through the wonderful alleys in the village of Emporios with its picturesque houses, and – of course – a boat trip to the swimming spots of neighboring Gyali, the island of pumice stones. -Vlassis Kostouros
Ferry from Piraeus (12-14 hours). Flight to Kos, then local boat (50 mins).
Blessed with somE of the best beaches – Livadi and Petra are two of them – and one of the most stunning island capital villages in Greece, Patmos caters to a sophisticated crowd. Due to the venerable presence of the Monastery of St John, the island has shunned the noisy night-life and madding crowds which have taken over elsewhere. Many affluent Europeans, charmed by the austere beauty of the old town surrounding the fort-like monastery, bought and restored old houses here. They spend several months of the year here, giving the island an international allure. -Alexandros Massavetas
Ferry from Piraeus (8 hours). Flight to Leros or Ikaria, then catamaran (50 mins).
If you’re in the mood for a quiet vacation, this tiny island is just what you need. You won’t find nightlife or ancient sights, but you’ll swim off some of the most beautiful beaches in the Dodecanese. You’ll eat well, too; at Taverna Manola on Avlakia Beach, Giorgos and Maria serve amazing dishes using meat and vegetables from their own farm. Vathy Beach, a 30-minute walk through olive groves, has no restaurant but it does have generally calm waters. N.D. Don’t forget to buy salt and herbs. You’ll be helping the locals and providing yourself with a great souvenir. -Marina Petridou
There’s no direct route. Local ferries cross from Kalymnos in 45 minutes.
Be generous with your time here. There are miles of gorgeous sandy beaches, but it’s the architecture that makes this island unique. The medieval Old Town – a legacy of the Knights Hospitaller – is among the largest Gothic settlements in the Mediterranean to have survived intact. A walk along the arched alleys after dusk proves that it hasn’t lost any of its magic. Italian rule (1912-1947) produced some delightful architectural extravaganzas: check out the buildings in Mandraki, the Kallithea Springs and the ruined mountain village of Eleousa (Campochiaro)! -Alexandros Massavetas
Direct flight from Athens. Ferry from Piraeus (13-18 hours).
The Monastery of Panormitis, the delicious shrimp, the wild prickly pears and the rich local cuisine influenced by the travels of the island’s sponge divers: all this is Symi. In Gyalos, its impressive port, you’ll see colorful neoclassical buildings that compose one of the most beautiful settlements in the Aegean. Most beaches on the island are only accessible by sea so it makes sense to rent a small craft, take a water taxi or join an organized boat excursion to visit them. Be sure not to miss Aghios Georgios Dysalonas beach, with green waters and breathtaking, 300-meter-high cliffs. -John Papadimitriou
Ferry from Piraeus (15-16 hours). Flight to Rhodes, then catamaran or local boat (1-2 hours).
Peace and quiet: this is what you’ll find on Telendos, as there are no cars here. Any sense of commotion here only lasts as long as it takes for the small ferry from Kalymnos to load and unload passengers. Telendos, covering just five square kilometers, is ideal for hiking. It has a small port with a taverna, four or five beaches and ruins from early Christian times that lie, visible to snorkelers, at a shallow point on the seabed. The longest route you can walk is a 2km path that leads to the ruins of a Byzantine settlement, where you’ll also find a small church offering amazing views. The island also lends itself to alternative tourism in the form of rock-climbing, an activity that reveals a wholly different Telendos. -Olga Charami
Ferry from Myrties in Kalymnos (10 mins).
Every year, more and more foreigners choose Tilos as their permanent residence. You can see the investment they’ve made as you spot the many restored houses in the capital, Megalo Horio, with its narrow alleys and cobbled square. These houses aren’t the island’s only imposing structures, however; on Tilos are the ruins of seven fortified settlements. At the Paleontological Museum, you can look even further back in time; there are bones of dwarf elephants that lived here tens of thousands of years ago. The island has an extensive network of hiking trails, but what it doesn’t have are any public garbage bins; a zero-waste program is being piloted here. -John Papadimitriou
Ferry from Piraeus (13-15 hours). Flight to Kos or Rhodes, then catamaran (1.5-2 hours).