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Greece by Sailing Boat

Greece by Sailing Boat

Ionian Islands, Saronic Islands and Dodecanese Islands

If you’re looking for a holiday that combines sea and history, book your sailing holidays with Skipper Armatori. Our flotilla cruises follow spectacular itineraries that touch enchanting beaches of unspoiled islands and historic sites of Greece. A sailing boat holiday in Greece with Skipper Armatori will lead you to experience the emotions of the sea and navigation with your family, friends and other people you will meet during the cruise.

Our Itineraries

Skipper Armatori has twenty years of experience organising sailing holidays in the Mediterranean. Thanks to our experience, we have developed three itineraries dedicated to Greece. Each itinerary focuses on a specific group of the countless and stunning Hellenic islands, namely:

Ionian Islands with Embarkation in Lefkas

The discovery of Greece by Boat begins with the Ionian islands (Lefkada, Ithaca, Kefalonia, Zakynthos). Our experienced skippers will take you to these islands’ most evocative and spectacular places. This region of Greece is mainly known for its long beaches with white sand and crystal-clear waters, the exciting colours of its landscapes, the magic of its small towns and the typically Mediterranean warmth of its inhabitants.

Navigation map of the Ionian Islands for sailing holidays in Greece with Skipper Armatori. The map shows popular destinations the cruise covers, such as Corfu, Lefkada and Zakynthos. A week-long holiday discovering the Greek Mediterranean and the fascinating islands of the Peloponnese.

  • Saturday: Lefkada
    • Check-in (boarding time) starts from 4 pm. The sailing boat usually departs on Sunday morning. Still, it will be possible to leave earlier depending on the arrival of guests and/or the early check-in booking (for exclusive boats).
  • Sunday: Lefkada > Meganisi > Kastos
    • The cruise develops towards the island of Meganisi, where we will visit the giant cave. A few miles further, we will visit the two splendid bays of the island, where we will stop for lunch and swimming. We will spend the night in the main bay of Kastos.
  • Monday: Kastos > Atoko > Ithaca
    • We will sail towards the uninhabited island of Atoko early in the morning. Atoko is located in the centre of the Ithaca Channel. We will moor in the splendid bay where the colours of the sea are indistinguishable from the colour of the sky. In the afternoon, we will head towards Ithaca, an island full of history and charm. At sunset, we will discover the typical Greek taverns in the area.
  • Tuesday: Ithaca > Sami
    • After restocking our galley, we will head towards Telemachus, the most beautiful bay on the island of Ithaca.
      A stop at Pigadi is generally planned in the afternoon, where ivory-coloured beaches await us. Chasing the sunset, the wind will accompany us to Sami (island of Kefalonia).
  • Wednesday: Sami > Fiscardo
    • We will sail up the Kefalonia channel for about a dozen miles; we will arrive at the olive bay or Andorvata bay south of Fiscardo. We will reach Fiscardo in the afternoon as it is very popular with yachters passionate about Mediterranean cruises (it’s the Greek Portofino).
  • Thursday: Fiscardo > Vasiliki > Sivota
    • We will cross the channel that divides Kefalonia from Lefkada, heading to the port of Vasiliki. We will sail for 10 miles to the bay, characterised by turquoise waters. We will spend the night in Sivota, toasting with a good glass of wine in the characteristic taverns of this area overlooking the sea.
  • Friday: Sivota > Skorpio > Lefkada
    • We will circumnavigate the island of Skorpio, owned by the Onassis family, and choose where to have lunch. In the afternoon, in another small bay, it will be time for the last swim of the cruise. When the wind blows steadily on the sails, we will gain the channel that will take us back to Lefkada.
  • Saturday: Lefkada
    • Check out. Disembarkation is scheduled by 10:00 am.
Isole del SaronicoQuota Individuale
Giugno€790,00
Luglio€790,00
Agosto€890,00
Settembre€790,00

Saronic Islands with Embarkation in Athens

The second option to discover Greece by Sailing Boat is The islands of the Saronic Gulf, close to Athens, between Attica and the eastern part of the Peloponnese. It is an ideal area for sailing cruises as it is sheltered from the Meltemi wind, which instead blows impetuously in the Cyclades in July and August. The islands we will visit with this cruise are also beautiful, with crystal-clear beaches, unspoiled bays and small fishing ports. One of the characteristics of the Saronic Islands cruise is the high number of ancient temples, Byzantine castles and neoclassical palaces. We recommend this cruise to people interested in learning about the famous places of ancient Greece and people who typically have a passion for history, art history, and archaeology.

Detailed navigation map for Greece by Boat to the Saronic islands with Skipper Armatori. The map highlights the Ionian Islands, Saronic and the Dodecanese. Skipper Armatori's navigation areas are marked with anchor and sail icons, showing the routes to explore the idyllic coasts and rich Greek historical sites, the favourite destinations for sailing holiday enthusiasts.

  • Saturday: Athens
    • Check in from 4:00 pm to midnight. The crew will meet with our staff at the meeting point inside the Athens marina, transfer to the boat, assign cabin assignments, and review the safety and coexistence rules on board.
  • Sunday: Athens > Aegina > Agistri
    • We will set sail towards the Island of Agistri in the morning. Subsequently, after a nice swim on the north coast of Aegina, we will visit the historic ancient theatre of Epidaurus in the afternoon. We will sleep in the bay of Apónissos, a huge rectangular pool with transparent seabed on light sand. An extremely evocative location.
  • Monday: Agistri > Poros
    • We will head towards Poros, an island with discrete and secluded beaches, crystal-clear sea, and rich Mediterranean vegetation. We will spend the evening in the village, stocking up on water and enjoying the lively nightlife that animates the island between the clock tower and the neoclassical buildings.
  • Tuesday: Poros > Dokos
    • Tuesday is the time to sail towards the small island of Dokos, a place of spirituality inhabited and cared for by a small community of only 10 monks. The island of Dokos is rich in hidden coves, offering snorkelling enthusiasts experiences. Dokos is the site of the discovery, by Cousteau, of the oldest wreck ever discovered (2,200 BC).
  • Wednesday: Dokos > Spetses > Hydra
    • We will head towards the island of Spetses, which owes its name to the Venetians, who called it the island of spices for the scents of Mediterranean herbs emanated by its vegetation. After various swims, we will continue towards the north side of Hydra, where we will spend the night in the bay.
  • Thursday: Hydra > Poros > Aegina
    • After breakfast, we will set sail towards the north coast of Poros, where we will have lunch after a nice sail. In the afternoon, not before a refreshing swim, we will continue towards Aegina. A famous and renowned island for its ceramics. Here, we will spend the night enjoying excellent grilled fish in a local trattoria.
  • Friday: Aegina > Athens
    • On the last day, we will sail towards the east coast of the island of Aegina. We will visit the many bays with crystal-clear waters characterising this picturesque island. During the navigation, it will be possible to see the house of the well-known citizen “Zorba the Greek” from the sea. We will return to Athens in the evening.
  • Saturday: Athens
    • Check out. Disembarkation is scheduled by 10:00 am.
Isole del SaronicoQuota Individuale
Giugno€790,00
Luglio€790,00
Agosto€890,00
Settembre€790,00

Dodecanese Islands with Embarkation in Kos

Our Dodecanese Islands Cruise is the third option to discover Greece by Sailing Boat. It is an authentic marine paradise of over 163 islands and islets positioned at the extreme limit of the Aegean Sea, the last outpost of Europe a few miles from the Turkish coast and Crete. These Greek islands are all different, each with its particularity, all united by the white of the houses, the beautiful beaches with turquoise water and a lively nightlife. The Dodecanese is a mix of history, art, and culture, and the beauty of the sea and the hospitality of the people make the cruise magical and unforgettable.

Nautical chart showing the navigation areas in the Dodecanese to discover Greece by Sailing Boat with Skipper Armatori. Points of interest such as Kos and Rhodes are highlighted, ideal for sailing holidays that combine relaxation and cultural discovery.

  • Saturday: Kos
    • Check in from 4:00 pm to midnight. The crew will meet with our staff at the meeting point inside the Kos marina, transfer to the boat, assign cabin assignments, and review the safety and coexistence rules on board.
  • Sunday: Kos > Leros
    • We set sail in the morning towards Leros, arriving in the early afternoon after a nice sail. We will be anchored for swimming and photos at Platanos, the island’s capital, where an ancient amphitheatre stands under an imposing castle that we can visit. Anchoring for the night is planned at the islet of Arkangelo.
  • Monday: Leros > Arki
    • After breakfast, we head towards Arki, a tiny fishing island a few miles from the Turkish coast. The island has thirty inhabitants and boasts beautiful sandy beaches and a sea with changing blue shades. We will spend the night in one of the beautiful bays in the area.
  • Tuesday: Arki > Patmos
    • Morning sail towards Patmos, the island with the imposing monastery of Aghios Ioannis that dominates the port from the hill above. Anchoring in a sheltered and quiet bay for lunch and swimming. In the afternoon, a small transfer close to the port to visit Chora and its monastery.
  • Wednesday: Patmos > Lipsi
    • In the afternoon, the navigation will take us towards Lipsi, a location characterised by beautiful bays. We anchor in one of these for lunch and swimming. We will visit the picturesque square, with houses in full Greek style white with doors and windows coloured in blue. There are taverns, small bars, and the church of Panaghia Charou, built at the beginning of the 17th century.
  • Thursday: Lipsi > Leros
    • Route towards Leros, on its west side. An island rich in small hills and deep green gulfs,
      picturesque valleys, jagged coasts and a Franco-Byzantine fortress that overlooks the capital. Moving in the afternoon to Lakki, the largest and safest port in the Dodecanese, and visiting the island by scooter.
  • Friday: Leros > Kalymnos > Kos
    • We will depart early in the morning, heading south towards the mountainous Kalymnos, with a stop for a swim and then reach the island of Pserimos. Its bay on the east side allows for safe anchoring in a truly special setting. In the afternoon, the last few miles to reach Kos and spend the evening celebrating together the last night on the boat.
  • Saturday: Kos
    • Check out. Disembarkation is scheduled by 10:00 am.
Isole del DodecanesoQuota Individuale
Giugno€790,00
Luglio€790,00
Agosto€890,00
Settembre€790,00

Choose a Sailing Boat Holiday in Greece with Skipper Armatori

Our cruises are designed to meet everyone’s needs. We have the right option for you whether you are single, a couple or with a group of friends – With Skipper Armatori, you can opt for the following:

  • Shared Boat
  • Exclusive Boat

Shared Boat

Cabin boarding gives you the freedom to book just one cabin with the possibility of adding more friends later until you reach, if you want, a boat just for you. The itinerary outline is published for each day, but the skippers will decide with the guests on board the schedule of the days or variations on the itinerary. It is possible to choose, if available, cabins with private bathrooms.

Exclusive Boat

Here, it is possible to immediately choose the type of sailing boat or catamaran with 2, 3, 4 or 5 double guest cabins from a selection of vessels of different years (including newly launched models) and in different marinas of embarkation with a skipper chosen by us or in the bareboat formula without a skipper.

Holidays by Sailing Boat or Catamaran

With Skipper Armatori, you can choose to take a cruise in Greece with two different types of vessel:

  • Sailing Boat
  • Catamaran

To discover more details about these types of vessels, you can consult the dedicated page. Remember that the catamaran, with a higher cost than the traditional sailing boat, very often has limited availability.

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