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!

14
Days

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
Day 1

Marina Zea

The day's sailing

0 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

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.

Day 2

Marina Zea to Cape Sounio

The day's sailing

30
Nautical miles
4.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Marina Zea to Cape Sounio

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

Temple of Poseidon in Cape Sounio

Visit the Temple of Athena

The Temple of Athena is well worth a visit and is located on a low hill approx. 300 m northeast of the temple of Poseidon.

Day 3

Cape Sounio to Kythnos

The day's sailing

30
Nautical miles
4.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Cape Sounio to Kythnos

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

Cyclades Itinerary

Visit Katafiki Cave

Katafiki Cave is one of the largest and most famous caves in Greece, which was used as a shelter by locals from invasions. You will get the opportunity to walk the narrow paths and discover several archaeological sites.

Kythnos, Cyclades Itinerary

Relax in the Thermal Springs

Head over to Loutra and relax in the renowned thermal springs, which are rich in iron and sulfer making the perfect free spa treatment.

Day 4

Kythnos to Serifos

The day's sailing

24
Nautical miles
3.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Sunsail Yachts, Cyclades Itinerary

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, Cyclades Itinerary

Visit Serifos Piazza Square

This cosy square, situated in Chora, the capital of Serifos, is the perfect lunch spot with several ouzeries and tavernas. As the capital is perched on a hill, you will get amazing views of the Aegean sea, and the perfect spot to watch the sunset.

Day 5

Serifos to Sifnos

The day's sailing

16
Nautical miles
2.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Sifnos, Cyclades Itinerary

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, Cyclades Itinerary

Visit the Monastery of Chrissopighi

This 17th Century Monastry was built on a craggy rock and is the most important pilgrimage site on the island. It has been painted beautiful shades of pink and orange, making it a stunning photo stop.

Day 6

Sifnos to Milos

The day's sailing

23
Nautical miles
3.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Milos, Cyclades Itinerary

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

Cyclade Islands

Visit the Pirate Caves

The caves - Papafrangas, Sarakiniko, Katergo - were used as hideouts for pirates of the Middle Ages, where traces of their ships are found next to the caves. In Sarakiniko, you will experience a spectacular landscape with white rocks of different shapes.

Milos, Cyclades Itinerary

Stroll around Little Venice

Wander around this quaint hamlet, level with the water, where the ancient port of Milos used to be.

Day 7

Ios

The day's sailing

19
Nautical miles
3 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Ios, Cyclades Itinerary

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

Beach in Cyclades

Party at Mylopotas beach

The secluded Mylopotas beach is one of the most popular beaches, where travellers often visit the renowned Far Out Club at the end of the beach.

Theatre, Cyclades Islands

Visit Odysseas Elytis Theatre

Named after a famous Greek poet, the open air amphitheater of Odysseas Elytis resembles ancient Greek theatres and is the perfect place to watch local performances and festivals.

Day 8

Small Cyclades (DHENOUSSA - IRAKLIA – SKHINOUSA – KOUFONISIA)

The day's sailing

20
Nautical miles
3 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Small Cyclades

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

Snorkelling, Cyclades

Nearby Islets Schinousa

The islets Aspronisi, Ofeidousa and Argilos are located at the northern part of the island and can be visited by boat. You should not miss the opportunity to explore them and swim in their charming, cooling waters which are ideal for snorkelling or spear fishing.

Cyclades Cave

Stop off at the Cave of the Sacred Icon of Agios Giannis

This is Iraklias most interesting walking destination, around 2 hours from the main port. The entrance leads to a sequence of caves with an abundance of stalagmites and stalactites.

Day 9

Paros

The day's sailing

29
Nautical miles
4.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Paros, Cyclades

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

Paros Sunset

Explore Paros Environmental and Cultural Park

Situated on the Agios Ioannis Detis peninsula, this park is an area of approximately 80 hectares of remarkable rock formations, caves, hidden coves and seashores with crystalline waters.

Day 10

Mykonos

The day's sailing

20
Nautical miles
4.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Mykonos

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

Little Venice, Mykonos

Visit Little Venice

A romantic, picturesque area of the main town, and is a great spot to have a drink and enjoy the sunset from one of the many bars along the waterfront.

 Sacred Islet of Delos

Explore the sacred islet of Delos

Delos is one of the most important archealogical sites in Greece. Under the Ministry of Culture's guidance, vessels need special permission to dock. Overnight stays are prohibited.

Day 11

Syros

The day's sailing

28
Nautical miles
4.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Syros, Cyclades

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.

Cyclades Sailing Itinerary

Head to Vaporia

The most glamorous and picturesque area in Ermoupolis, with impressive Venetian mansions that give amazing view to the Aegean Sea.

Loukoumia

Taste the local sweet

Try the mouthwatering, addictive loukoumia, which is Turkish delight in English. They are soft and chewy sweets, flavoured with rosewater, pistachios and almonds.

Day 12

Kythnos

The day's sailing

36
Nautical miles
5.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Cape Sounio to Kythnos

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

Cyclades Itinerary

Visit Katafiki Cave

Katafiki Cave is one of the largest and most famous caves in Greece, which was used as a shelter by locals from invasions. You will get the opportunity to walk the narrow paths and discover several archaeological sites.

Kythnos, Cyclades Itinerary

Relax in the Thermal Springs

Head over to Loutra and relax in the renowned thermal springs, which are rich in iron and sulfer making the perfect free spa treatment.

Day 13

Kea

The day's sailing

22
Nautical miles
3.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

Kea, Cyclades

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

Stone Lion of Kea

See the Stone Lion of Kea

A short hike from Loulida is one of the most popular sights of the island, dating back to 600 BC.

Diving, Cyclades

Dive amongst the shipwrecks

Kea is a diving paradise with two shipwrecks to explore: the British liner HMHS Britannic, one of the largest liner wrecks in the world, and the S/S Burdigala, a luxury liner built in the late 19th century. Snorkelling is a must too, with colourful marine life.

Day 14

Marina Zea

The day's sailing

43
Nautical miles
6.5 hr
Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Suggested activities

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.