ASTYPALEA
Hang out with the locals
The Bokan café (Tel. (+30) 22430.623.15) opened its doors in Hora, the island’s main port, in the winter mostly for the local community which, outside the summer months, has very few choices for coffees and snacks. Genuinely eco-friendly – e.g. its straws are made from 100% wheat by the social cooperative Staramaki. It supports the products of small, Greek businesses, it’s open until 2 am, it doesn’t change its prices for tourists, and, apart from exceptional coffees, it serves fresh snacks.
Grandma’s house
You write down your name and order on the notepad, you get your cold beers yourself and Mrs. Maria calls you from the window when your order is ready. All the dishes are homemade, while the kitchen teems with fresh fish and delicious mezes. This is what you’ll expect to find at Galini (Tel. (+30) 22430.612.01), the only taverna at the remote bay of Vathi.
A remote beach
 
The beach of Aghios Ioannis o Makris is the oddest common secret of Astypalea. Everyone knows about it, yet very few people go because it’s a 10-km drive along a dirt road followed by a 30-minute downhill walk, which, on the way back, turns into an uphill hike. As such, it continues to be a remote, beautiful beach. The trail begins from the namesake church that offers a magnificent view of the sunset. Make sure you stock up on supplies before you go!
KALYMNOS
A magical getaway
Kalymnos is a beautiful island that has a lot to offer. However, if you’re looking for a change of pace, there is a boat that leaves every day from the small port in Myrties every 30 minutes from 8 am to 1 am for the island of Telendos that lies just across the strait. Naturally, the peak hours are in the afternoon, so it’s best to go in the evening. Take a dip in the cool waters, visit the old Christian necropolis and the basilicas, or watch the sunset from Aghios Giorgios and end your trip at Το Kapsouli (Tel. (+30) 22430.473.63), a small local taverna.
KASOS
The festival of the shepherds
The festivals of Kasos are famous for their authenticity, customs, music, and extraordinary local cuisine. On September 2, a festival is held at the monastery of Aghios Mamas, the patron saint of shepherds, at a beautiful, remote location. As there aren’t many people, the experience is even more special.
KARPATHOS
The sweet nectar of Othos
The sweet wine from the town of Othos is the island’s best kept secret. It’s produced in small quantities, not exported off the island, and is served only at local festivals and coffee shops. If you don’t find it in the coffeeshops, ask the local show you can get it directly from the producers.
A quiet escape
Aghios Minas is not an unknown beach, but it will continue to remain a quiet beach as long as it is accessible only by a rocky dirt road on the northern and, consequently, more remote part of the island. A long beach that boasts crystal blue waters, tamarisk trees that offer shade from the sun, and two small tavernas that serve delicious mezes.
KASTELLORIZO
400 steps at sundown
A little before the sun goes down, follow the so-called “400 steps” that lead up the rock that towers over the island’s main town and towards the monastery of Aghios Georgios tou Vouniou. The views are breathtaking and, late in the evening, as the lights of the houses of the town below and along the Turkish coast slowly turn on, the views become even more spectacular.
KOS
Wine tasting
Nestled under Mount Dikaios, close to the sea, the vineyards of the Hatziemmanouil (Tel. (+30) 22420.688.88) and Akrani wineries (Tel. (+30) 22420.698.60) extend across the region of Asfendiou. The fact that the two wineries neighbor each other and cultivate different varieties create the perfect conditions to organize a 3 or 4-hour wine tasting tour.
A walk in a medieval settlement
The “Mystras of the Dodecanese,” as Palaio Pyli is known, is located almost in the center of the island. Here you’ll find the ruins of a medieval settlement of the 11th century BC that was built on a natural fortification and protected by a castle. Visit the site in the evening in order to avoid the heat, take a walk around the ruins, and enjoy the views of the nearby islands of Pserimos and Kalymnos.
Turquoise waters
 
To reach Cavo Paradiso, the island’s southernmost beach, you will need to follow the signs of the dirt road that leads to Aghios Mamas. The landscape here is exotic: endless sandy beaches, turquoise waters, and imposing sand dunes. There are a few umbrellas and sunbeds, but generally the beach is not crowded.
LIPSI
Ouzo and mezes
At the far end of the port, the small ouzeri Aspraki (Tel. (+30) 22470.412.73) has been serving delicious mezes and fresh fish since 1956. Take a seat at one of the tables that are set out in front of the esplanade and, with a glass of chilled ouzo, enjoy grilled octopus, fried zucchini balls, homemade eggplant salad, and a seafood dish with orzo.
A rare local wine
In 2013, Manolis and Nikos created the Lipsi Winery (Tel. (+30) 697.461.6135) with the aim of reviving the Fokiano, a rare grape variety that came from Phocaea in Asia Minor and was traditionally cultivated on the island for the production of a sweet wine. Their xeric grapevines are planted in an almost amphitheatrical form on the slope of small hill that looks out to sea. This year, Manolis and Nikos produced a few bottles of an old Fokiano from 2008.
Hidden beach
 
On the western side of the island, under the Monastery of the Dormition of the Virgin Mary (“Koimisi tis Theotokou”), lies the namesake beach that is hidden from the world. The beach is small and quiet, there is no shade, it has turquoise waters and pebbles. Make sure you have everything you need and go early in the morning or late in the afternoon to avoid the heat.
LEROS
The breathtaking views from Profitis Ilias
Next to the island’s castle, overlooking the town of Aghia Marina, stands the little church of Profitis Ilias, with spectacular views of the bay of Alinta. Walk up the road that goes from Platanos towards Aghia Paraskevi and continue on the trail with the many steps. Rest along the wall and enjoy the view as the sun slowly sets behind the horizon.
Α traditional fishing village
At Panteli, the small fishing village close to Aghia Marina, it seems that time stopped in the 1980s. Small, white houses, caïques (traditional fishing boats), fishermen making nets, fish tavernas, and windmills create an idyllic scenery. Panteli is known for its beautiful waters and fresh fish.
NISYROS
A walk around Emporios
Built on the edge of the caldera, hidden from the sea, Emporios was previously abandoned after the earthquake of 1933. A cave stands at its entrance that, due to the heat from the volcanic activity, functions as a natural sauna. In the evening, the village is ideal for a walk along its cobbled streets, as well as to the castle and the Byzantine church of Archangel Michael.
MARATHI
Not just for fresh fish
On the small island of Marathi, in a quiet sandy bay, without any cars, the restaurant of Pantelis (Tel. (+30) 22470.326.09) has been serving fresh fish and seafood next to the sea since 1978. An ideal place to swim, read, and have dinner under the moonlight that reflects off the sea.
PATMOS
Under the tamarisk trees
For many people, Psili Ammos with its crystal waters is the island’s best beach. Try to get there as early as possible to find a spot under the few tamarisk trees that provide shade from the sun.
Refreshing cocktails
The small cafeteria Holy (Tel. (+30) 22470.347.44) at Skala makes refreshing cocktails. It has a large selection of drinks, while you can also find select Greek wines, which they serve by the glass. They are also open in the morning for coffees, snacks and finger foods.
RHODES
Rhodes on a plate
Paraga (Tel. (+30) 22460.912.47) in the town of Apollonais is not your ordinary taverna. They serve pies and breads, local meats and legumes, but their dishes are based on old, traditional Rhodian recipes that they have gathered and arranged with great care. Their menu also includes complex dishes, such as lamb shoulder prepared in a wood-stove oven and served in clay shell that resembles a small earthenware jar, and unleavened wheat bread – the preparation of which is a sacred ritual.
A well-hidden beach
The locals like to keep Kokkini Ammo a secret. It is a small beach tucked between rocks and caves that is accessible only by boat. It is located 35km east of the city of Rhodes, between the towns of Charaki and Archaggelos. It has shallow, emerald waters, fine sand with a reddish hue, and offers some much-needed shade, especially in the late afternoon.
SYMI
The Novena of the Virgin Mary at Nimos
Nimos is a desert island that lies to the north of the port of Symi. On August 24, the little church that is dedicated to Aghia Pakou celebrates the Novena of the Virgin Mary. In the evening, boats will take you to the island for the festival. In general, do not miss the opportunity to attend the festivals of Symi where, usually after the church service, “akoumia” – a sweet specialty made from boiled rice – are offered.
A day at Toli
Toli is a beach on the southern side of the island, just 25 minutes by car from the port. On the way, it’s worth stopping at the fortified monastery of the Archangel Michael Roukouniotis, with its characteristic cypress tree that stands in the middle of the courtyard. After a day at the beach, have lunch at Dafnes (Tel. (+30) 697.443.0138), where you can try the lamb from the family’s own flock, fresh fish of the day, and the local thyme honey.
Cakes and pastries at sunset
 
Inside the labyrinth of the Church of Panormitis you’ll find the Panormitis bakery (Tel. (+30) 22460.700.70), where the most delicious cakes, aromatic cheese pies with spearmint, and buttery, unsweetened traditional “simits” (circular bread) are made in a traditional wood-oven stove. You can enjoy them as you watch the sunset.
TILOS
Fresh fish with a view
At the small port of Aghios Antonios, with its caïques and tall tamarisk trees, To Delfini (Tel. (+30) 22460.442.52) sets its tables out on the slated pavement. With views of the volcano of Nisyros, To Delfini has been serving fresh fish and Greek traditional dishes – the lamb on parchment paper is sublime – for the past 40 years.
HALKI
Beach hopping
Caïque are the island’s main means of transportation, as many beaches cannot be accessed by land. Areta is a small bay with a white pebbled beach, turquoise waters and high rocks that offer shade. At Tracheia, you will find two small beaches, while the boats that leave from the port can also take you to Alimia– a small nearby island that is located between Halki and Rhodes.
PSERIMOS
Inspired frontiersmen
At Manola (Tel. (+30) 22430.515.40), George and Maria, a young couple that permanently lives on the island, prepare dishes with local wild goats, their own olive oil and salt, and local grape leaves. They do a remarkable job with the few means they have at their disposal on this small frontier island of the Aegean Sea, which lies off the coast of Turkey. At Manola, you can enjoy the most delicious and softest lamb with pasta, as well as fresh fish that George and Maria catch themselves.