Day 2. Kalymnos - Astipalia

Snorkel in pristine waters alongside steep cliffs before moving on to the scenic harbour of Pothia. Stroll through the narrow alleyways of the village, enjoying local architecture and some shopping. History enthusiasts are invited to visit the Archaeological Museum of Kalymnos.

Your next destination, the island of Astipalia, lays forty nautical miles away from Kalymnos. Start your cruise and in about four to five hours you’re there. Also known as Astypalea, it is a Dodecanese gem with a Cycladic soul. Drop anchor in front of the main town of Astipalea and explore its maze of narrow streets, whitewashed houses, tavernas and cafes. Stop at a cafe and try some delightful cheese and rakomelo, a locally produced alcoholic drink mixed with honey.

Enjoy the views and the sunset from alongside the hilltop ruins of a castle.

Day 3. Astipalia - Amorgos

Spend the morning enjoying swimming and water sports in one of the island’s lagoons. Relish the feeling that you’re somewhere at the edge of the world, enjoying the simpler things in life. The scent of wild herbs, the sea, and warm winds blend into a poetry of life. That poetry has a rejuvenating effect on those who travel to Astypalea.

When ready, set sail to Amorgos, famous for its white monastery of Hozoviotissa, the second oldest in Greece. Set into a sheer cliff face, it looks surreal at a height of more than 350 meters. Save the visit for the next day, perhaps right after the breakfast.

Tonight, walking up the hill from Ormos to Langada gives you a chance to explore the island and get in some good exercise, too!. Once at Langada, you will enjoy dinner with a view at one of the tavernas. If you don’t favor long walks, it is also possible to take a taxi the three and a half kilometres cup the hill.

Day 4. Amorgos - Koufonisia

The next day, enjoy the wild coastline of Amorgos, accessible only by boat. One of the places we recommend you visit is Megali Glyfada, a beach hidden inside a natural, fjord-like cove located north of the island. Discover Chora, as an alternative: this is a gorgeous little village located on top of the hills. You’ll fall in love with its picture-postcard views over a Venetian castle, windmills, traditional Greek churches and houses of Cycladic design.

If you’re a fan of Luc Besson’s movies, you’d love the fact that most of the scenes from his famous movie, “The Big Blue”, were filmed here at Amorgos.

When ready, set sail for your next destination - the island of Koufonisia - another of the charming Greek summer spots that are quiet and edenic and where you won’t see crowds of visitors.

Koufonisia is a complex of several islands. Inhabited Pano Koufonisi is where all the touristic facilities are located. Kato Koufonisi is a paradise with crystal-clear turquoise water. Upon arrival, swim in an idyllic anchorage and then spend the evening wandering in the old town, Chora Koufonisia. Sample some delicious local specialties and revel in the picturesque beauty of your surrounds.

Once you have returned to the yacht, you may wish to opt for a quieter night and head out to a nearby bay.

Day 5. Koufonisia - Ios
Today’s destination is Ios. You may ask your captain to leave Koufonisia at sunrise and wake up to the gorgeous views of what’s known as the “Island of Youth". Ios is known for its vibrant nightlife, which is why it’s usually visited by young travelers from all over the world who come to enjoy all that’s local in the way of local bars, clubs, restaurants, and cafes. The buzz and the vibrancy of the place is palpable. Right after breakfast, enjoy swimming and diving in the clear blue sea and soak up the sun.

Don’t miss your chance to take an afternoon siesta in readiness for a night out on the island’s main town, Chora. If you’re not a fan of the local party scene, enjoy instead, a leisurely walk around the village or visit the church of Panagia Gremiotissa and savor the imposing views.

Day 6. Ios - Naxos

Leave early for Naxos, one of the largest islands of the Cyclades group.

This is the island to which Theseus, slayer of the Minotaur, sailed from Crete. There, he abandoned his wife Ariadne who immediately took up a somewhat debauched existence with Dionysus. In 1210 AD, the island became a duchy of Venice, and it was the Venetian Duke, Marco Sanudo who built the large castle that now dominates the town. It is a great place to rent a motorbike to travel along some by-ways, with a must-see stop at the 7th Century BC marble statue of Dionysus at Apollonas.

Spend the afternoon exploring traditional Greek villages hidden between the slopes of a mountainous landscape or delighting in the beautiful golden sands on the beaches of the island.

Dine ashore in one of the waterfront tavernas or stay on board and enjoy peaceful sunset views from the foredeck of the yacht.

Day 7. Naxos - Paros

The last, but certainly not the least, destination for this sailing vacation is Paros. It takes between two and three hours to reach the island from the time the anchor is hauled up. Once you’re there, you’ll feel that it's the perfect place to end your "off the beaten track" sailing experience in Greece.

Paros gives the impression that "wild and fanciful" life has not stepped ashore, however you’ll find both the tranquil and the vibrant here. The main village of the island is Parikia, whereas Naoussa is famous for having a cosmopolitan vibe. Both have whitewashed houses that look like sugar cubes; ouzeries and restaurants; potted geraniums, clouds of bougainvillea, and fine restaurants. The picture-postcard style scenery is embellished with colorful caiques - small, traditional fishing boats.

Kolymbithres Beach, located near Naoussa is one of the most beautiful spots on the island. And it is also one of the most popular in the area for its strange rock formations. In summer, Kolymbithres Beach gets crowded, so you may not want to stay there if it’s a popular time of the day for sunning. Let your captain choose a nice bay nearby for an overnight anchorage and relax on board with dinner served by your chef and crew.