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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

Greece:

Cyclades

Duration:

10 days - 10 nights

Max number of passengers:

8 people

Available:

-

Suitable for travellers:

18 - 70 years

Boarding from:

Milos

What's included

Cancellation policy

avatar image

Super!

Organised by:

Andrea S.

Member since 2014 -

Organisation

Italian

Spanish

English

This experience, in a nutshell

Under a great sun, carried by the wind, from port to port, from cove to cove, we will discover the villages and landings of the Aegean islands: white villages clinging to the rock that look at you from above, jagged coasts, intense light and sun, a crystal clear sea, churches, castles and monasteries, together with a warm welcome. These are the Cyclades and Dodecanese Islands, the islands of light, which in mythology gave birth to heroes and gods. All the islands are wonderful, each with its own grace, each with its own story.


Red, white, gold, yellow, black, orange...  Milos is an island born from a volcanic eruption: nature has created art, the rocks are masterpieces of sculpture, its colored stones look like paintings, as well as the beautiful beaches. Petrification hides many minerals and the island is one of the oldest mines in the Mediterranean: before the Cyclades to be inhabited, it became an island of pirates for a long time! The famous Venus was found in Milos, now on display at the Louvre in Paris!


Enchanted by Milos, we'll set off to discover the Aegean on our way southeast.

The itinerary is very rich and admits multiple variants and itineraries: a ten-night holiday will allow us to travel without being pressed every day by the need to travel many miles. We will alternate days of navigation with stops on land to go and browse the sites of greatest interest, explore the islands by renting bikes, cars or scooters, stretch our legs and treat ourselves to some well-deserved relaxation and some swimming in the most beautiful coves.


Embarked in Milos, here you will refuel. In the evening we go out to visit Chora, from which we can admire a wonderful sunset. In the morning we set sail along Milos, Kymolos and Polyagios which, with their caves, stacks, cliffs of colored rocks, alone are worth the holiday. Continue to Ios, a festive and lively island. From here we aim for the Small Cyclades. The bays are a spectacle, the water is turquoise, the islands far from mass tourism. One or two stops for a swim and lunch and a stop for the evening: they are all beautiful, we are spoiled for choice. We then enter the Aegean towards Amorgos, a true jewel of nature and architecture in the middle of the sea. We go ashore and go to visit the incredible monastery. Rested, we leave for Astypalea from where we will arrive in Kos after another well-deserved stop.

This is the planned itinerary, the actual one will be decided on the spot based on the real weather conditions, listening to everyone's preferences but on the unquestionable decision of the Captain, who aims to ensure a pleasant and safe itinerary.


In bad weather it is possible to have to skip some stops or cross east from Amorgos skipping Astypalea.

For closed groups, it can be arranged to pass through Folegandros, Ios, Santorini and Anafi towards Astypalea, skipping the Small Cyclades and Amorgos.

No Departures available

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21+

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Boat & Classes of Service

Beneteau Oceanis Clipper 500 - 1991

Type

Sailboat

Length

15.3 m.

Toilets

3

Cabins

3

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18+

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Our itinerary

Our trip starts here:

Milos.

Check-in: 5:00 PM

Our trip ends here:

Kos Town.

Check-out: 8:00 AM

Leg 1

Day 1 - Embarkation

In the afternoon at 17.00 boarding begins, we settle on board and introduce ourselves, we go out to do the first refueling (galley) in a good supermarket on the island, in the evening then we go up to admire the sunset from the Chora of Apollonia and for a dinner in a tavern.

Leg 2

Day 2

After a good and healthy breakfast, we set sail and move on to visit some of the beautiful and surprising bays of Milos and Kimolos: caves, stacks, beaches of colored rocks, inlets, ravines, carved by the elements in the tuff, cliffs: in Milos, Kymolos and Poliagios, Nature has created art and men have dug shelters in the rock for fishermen's boats. A combination of great and unique beauty, which alone is worth the trip.

Day 2

Leg 3

Day 3

We set sail early to go and admire the natural beauty of the island of Poliagios, the largest uninhabited island in Greece, characterized by red rock and cliffs, crystal clear water and breathtaking coves. We have lunch anchored in a bay and continue towards Ios.

Day 3

Leg 4

Day 4

From Ios we continue eastwards towards the Small Cyclades, a handful of semi-deserted islets that boast crystal clear waters and deserted bays far from mass tourism, wonderful coves and small villages like jewels. We allow ourselves one or two stops to dive into these waters and have lunch and choose one of the islands for the night

Day 4

Leg 5

Day 5

From the small Cyclades early in the morning, we set sail towards Amorgos, relatively close. It is a surprising island, known for having been the setting for the film 'The Big Blue' and even more so for the incredible monastery carved out of the rock, which is still inhabited by a number of monks who lead a retired life there. Several landings are possible and the island is certainly worth a day's stop.

Day 5

Leg 6

Day 6

We stop for a day in Amorgos to relax a little and go calmly to discover the island, which is large and very interesting. There are several landings and several beaches to visit, to discover by land the monastery that is incredible and the different villages on the island. those who want can relax on the beach, those who want to go on an adventure aboard scooters or rental cars.

Day 6

Leg 7

Day 7

We set sail again and leaving Amorgos we head southeast towards Astypalea, a surprising island, in the shape of a butterfly, Astypalea is located in the center of the Aegean, it is not easy to reach, it has a jagged coastline full of islands and atolls, a part is completely uninhabited and wild, while the town is beautiful with the castle that surrounds the old city and overlooks the port and the bays below.

Day 7

Leg 8

Day 8

Visit to Astypalea Astypalea is a dream, an idea, lost in the middle of the sea and time. Only the real 'seekers' of Greek islands go this far.

Chora and the underlying port of Skala form a compact, proud, welcoming whole, dazzling under the scorching rays of the sun. The island belongs to the Dodecanese, but by affinity of spirit it is linked to the Cyclades, the architecture that has gone around the world is totalitarian, undisputed, queen here. Immediately after a walk in the center you get lost in an intrigue of square white houses and blue balconies and windows. There are many hidden bays, inlets, islets. to the discovery of which we will dedicate a day by land and sea.



Day 8

Leg 9

Day 9

We go back out to sea and take a swim in a bay of the island to the east; rested for the break and loaded again, we face in 3 or 4 hours of navigation the channel that separates Astypalea, the westernmost of the Dodecanese islands, from the western end of Kos. We enter the bay of Cefalo, where we go down for dinner.

Day 9

Leg 10

Day 10

From Kos we move to the eastern side of the island, taking a nice bath for the lunch break in the cove of Therma, which takes its name from the thermal waters that come out into the sea a few meters from the shore.

Day 10

Leg 11

Day 11

A last breakfast all together and we start the disembarkation: the holiday is unfortunately over, after a ritual photo, kisses and hugs with the promise to meet again, we say goodbye!

Day 11

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Andrea S.

Member since 2014 -

Organisation

Italian

Spanish

English

5.0/5

out of

44

reviews

Skipper

Boat

Destination

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From the Dodecanese to the Cyclades: sailing off the beaten track!

06/30/2025

elisabetta m.

-

Italy

Andrea è un professionista, sempre pronto a renderti felice! Abbiamo visitato posti stupendi e in condizioni di vento e mare piuttosto impegnative, che solo un esperto marinaio poteva rendere cosi' piacevoli!
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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

06/25/2025

Anna M.

-

Luxembourg

Andrea is an extremely skillful skipper, he knows exactly how to make you feel comfortable on the boat, he worries about your needs and is always ready to answer questions and curiosities. Our destinations were amazing and magic Greece just makes the rest. Highly recommended!
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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

06/19/2025

Elisa L.

-

United Kingdom

The trip was great. Andrea is a very experienced skipper and knows all hidden gems of Greece! Every day was full of surprises, including seeing turtles, tuna fishing, and local wine festival. I particularly appreciated Andrea’s attention to the environment and the promotion of a responsible, local and more authentic way of travelling. Highly recommended!
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The enchantment of the sea: Lefkada, Ithaca, Kefalonia and the smaller islands

09/30/2024

Veronica B.

-

Portugal

This was one of the best experiences I’ve had! Everything from the cabin, captain, crew and sea creatures was incredible. I can highly recommend everything about this trip. Grazie Andrea

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