Take the helm and enjoy our recommended two-week bareboat sailing holiday itinerary around the Cyclades islands, the most popular island group in the Aegean Sea. The name “Cyclades” refers to the islands forming a circle around the island of Delos, and these islands are some of the most beautiful in the world! Set sail from our Athens base and experience stunning sandy beaches, distinctive white and blue architecture, friendly locals, folk music and breath-taking landscapes as you island hop your way around the islands taking on the adventure one day at a time!
Cyclades sailing itinerary
Highlights
- Fantastic Saronic Sailing
- Sacred Island of Delos
- Little Venice in Mykonos
- The Temple of Poseidon in Sounio
- Serifos Cave of Koutalas
- Great hiking, diving and snorkelling
- Katafiki Cave in Kythnos
Marina Zea
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

Our base at Zea Marina is conveniently located just a short taxi or metro ride from central Athens. Explore the sights of this unique city, taking in the famous Acropolis and the Parthenon, or just soak up the atmosphere of Greece’s bustling capital. Stay in Zea Marina for the night and enjoy the area’s excellent tavernas or visit the compelling maritime museum.
Marina Zea to Cape Sounio
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
-
Exploring

Sounio is found at the southern tip of the prefecture of Attica. The rocky and steep landscape is home to the ruins of the ancient Greek temple of Poseidon, the god of the sea in classical mythology - an excellent spot to view the stunning sunset over the Aegean Sea. Today the wide area was declared a national park due to its environmental value.
Discover Cape Sounio
Cape Sounio to Kythnos
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
-
Shopping
-
Swimming
-
Exploring

Arguably one of the most beautiful islands close to Athens, Kynthos is popular amongst sailors for the many bays and coves to explore. The coastline has 99 beaches in total, perfect for relaxing and swimming - Kolona Kynthos beach is a must-see!
Discover Kythnos
Kythnos to Serifos
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
-
Shopping
-
Swimming
-
Exploring

Serifos is known for its multiple award-winning beaches and white-washed cubed houses contrasting with the natural landscape. After a day at the beach, stroll through the cobblestone narrow alleys and have a drink at one of the many bars in the islands capital, Serifos Chora.
Discover Serifos
Serifos to Sifnos
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
-
Shopping
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Swimming
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Exploring

Sifnos was once a thriving gold and silver mining location and has since developed a reputation for being cosmopolitan yet traditional. This picturesesque island is renowned for its cuisine and local crafts so indulge and immerse yourself in all that Sifnos has to offer.
Discover Sifnos
Sifnos to Milos
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

Milos is the most exotic island in the Aegean Sea and the most impressive with yellow, orange, white and red volcanic rocks scattered across over 70 beaches - Palaiochori, Papafragas, Gerontas, Firiplaka, Tsigrado, Plathiena beaches are definitely worth a visit!
Discover Milos
Ios
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

Sail to Ios, one of the top party Greek islands, renowned for its vibrant restaurants, bars and clubs. As well as the party atmosphere, Ios offers pristine beaches, magnificent views and mythological history.
Discover Los
Small Cyclades (DHENOUSSA - IRAKLIA – SKHINOUSA – KOUFONISIA)
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

Small Cyclades is a chain of small islands in the eastern part of the Cyclades. There are many Small Cyclades but only four are inhabited: Donousa, Iraklia, Skhinousa and Koufonisia. Spend your day exploring the islands, swimming in the crystal clear waters and enjoying a siesta. These peaceful islands offer ultimate relaxation after visiting party central, Ios.
Discover Small Cyclades
Paros
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

Paros is the third largest island of the cycladic complex boasting stunning mountainous landscape with 120km of coastline featuring sandy beaches and clifftop villages. Take advantage of the Meltemi wind and enjoy watersports such as kitesurfing and windsurfing.
Discover Paros
Mykonos
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

According to Greek mythology the island was the location of the battle between Zeus and the Titan and it was named in honor of Apollo's grandson Mykonos. Over the last 20 years the cosmopolitan Mykonos has became a popular summer holiday destination amongst all types of travellers, offering glamour and world famous nightlife.
Discover Mykonos
Syros
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
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Swimming
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Exploring

Ermoupoli is capital of Syros and the Cyclades. It is grand and impressive with marble paved squares, neoclassical buildings, and catholic and orthodox churches. The coastline is filled with beautiful beaches, with the most popular (Kini beach, Galissa beach, Delfini beach, and Dellagratsia beach) on the southern side of the island.
Kythnos
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
-
Snorkelling
-
Shopping
-
Swimming
-
Exploring

Arguably one of the most beautiful islands close to Athens, Kynthos is popular amongst sailors for the many bays and coves to explore. The coastline has 99 beaches in total, perfect for relaxing and swimming - Kolona Kynthos beach is a must-see!
Discover Kythnos
Kea
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
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Snorkelling
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Shopping
-
Swimming
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Exploring

Kea (or Tzia as it is also known as) stands out from the other Aegean islands for its rich flora, rare plant species, olive groves and vineyards. Discover 60km of exciting hiking trails leading to monuments, buildings, hidden coves, caves and beaches. It is also home to the largest oak forest in the Cyclades making it a great spot for birdwatching.
Discover Kea
Marina Zea
The day's sailing
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Suggested activities
-
Snorkelling
-
Shopping
-
Swimming
-
Exploring

Our base at Zea Marina is conveniently located just a short taxi or metro ride from central Athens. Explore the sights of this unique city, taking in the famous Acropolis and the Parthenon, or just soak up the atmosphere of Greece’s bustling capital. Stay in Zea Marina for the night and enjoy the area’s excellent tavernas or visit the compelling maritime museum.