Cyclades sailing holidays: island tour on the middle of the Aegean Sea!

Are you planning a sailing holiday in the Cyclades? When to sail, and what is the best sailing route? The Cyclades are very popular among boaters – the archipelago offers unforgettable experiences! You can explore more than 200 islands here, each providing you with a different adventure! There are countless beaches and diverse entertainment opportunities on these islands – explore them all! We will with the best itineraries, ports, yacht rental options & other useful information.

You can read in this article about the following topics:

• When to sail Cyclades?
• Why the Cyclades is good for sailing?
• Ports around the Cyclades
• Sail in the Cyclades! The Cyclades sailing holidays
• 2-weeks The Cyclades sailing plan
• 7 Days The Cyclades sailing tour
• Marine gas and boat gas stations in the Cyclades

When to sail Cyclades?

When you sail in the Cyclades depends on your priorities. Arguments and counter-arguments that will help you make a decision:

May, June and September

Advantages:
The weather is ideal, warm and sunny, with a pleasant average temperature of 20 C. The Meltemi wind (strong, dry northwesterly) is present, but generally less intense than in July/August, creating good sailing conditions. You will meet fewer tourists and more moderate prices.
Disadvantages:
In May, the sea can be a bit cooler, especially at the beginning of the month.
These months offer a fantastic balance of great sailing weather, comfortable temperatures and manageable loads.

July and August

Advantages:
The weather is warm and sunny and the sea temperature is perfect. Bustling life with bustling ports and festivals.
Disadvantages:
The wind can be very strong, especially in July, which makes sailing more challenging. You can expect more tourists and higher prices.
Other aspects:
If you are a beginner, May, June or September may be more suitable due to lighter winds. Experienced sailors can enjoy the challenge of the stronger Meltemi in July/August. If you want to visit many islands, take into account the possible effect of Meltemi and the ferry schedule in July/August. Check the sailing conditions and wind rose diagram of the Cyclades.

Why the Cyclades is good for sailing?

• Navigating the strong Meltemi in July and August requires skill and experience, making the Cyclades ideal for experienced sailors looking for an adrenaline rush. Planning your island hopping routes and timing can be an engaging navigational exercise. Choose routes and anchorages that provide shelter when needed.
• Each island has its own unique character, from the volcanic landscapes of Santorini to the whitewashed villages of Mykonos and the pristine beaches of Naxos. The Cyclades are perfect for island hopping, allowing you to discover different cultures, cuisines and landscapes within a short sailing distance. Despite the strong winds, the Cyclades offer many sheltered bays where you can anchor safely and enjoy picturesque harbor towns and calm evenings.
• Rich history and culture: Discover the ancient ruins and archaeological sites, remnants of the rich history of the Cyclades.
  Experience authentic Greek culture in charming villages with their narrow streets, whitewashed houses and friendly locals.
• The region is easily accessible from the ports of Athens and Lavrion and there are direct flights to several islands (Mykonos, Santorini).

What is the best sailing route in the Cyclades?

There’s no single “best” sailing route in the Cyclades, as it depends on your preferences, experience level, and the time you have available. Tthe most popular sailing ruotes in the Cyclades are: sailing from Athens to Mykonos and sailing from Athens to Santorini

Ports around the Cyclades

Lavrion Marina

Many sailors start at the marina of Lavrion in the eastern part of the Attica Peninsula, to the Cyclades. The port can accommodate up to 680 yachts. The maximum depth of the port built-in bay is 7 metres, and incoming yachts can be up to 30 metres long. yacht charter Lavrion, Lavrion sailing

Karavotsai Marina, Folegandros

The only major marina of Folegandros is quite small. It can accommodate boats with a draft of 4 m and a length of 60 m. Embraced by beautiful natural surroundings, the marina offers a water tank refill, bars, restaurants and a market. Folegandros sailing, Folegrandros boat rental

Ayios Nikólaos Marina, Kea

It is an important port on the island of Kea, close to beautiful golden beaches and excellent fishing spots. It can accommodate 255 yachts at the same time, with a maximum length of 50 metres. The water depth of the port is up to 8 metres.

Mérikha Marina, Kithnos

This tiny marina can accommodate about 30 yachts up to 60 meters long and has a water depth of 8 meters. Local hotels, restaurants, and lively nightlife areas in the immediate vicinity.

Ermoupolis Marina, Siros

Yachts up to 60 metres long can moor in the main marina of the tiny island of Siros. The water depth here is 9 metres. There are plenty of services available, including boat service and refuelling. Syros sailing, Syros yacht charter

Naxos Marina, Naxos

Yachts up to 20 metres in length and a number of 70 may berth in this marina. The maximum dive is 5 metres. In addition to the boat service, you can find the usual basic services in the marinas here. Naxos sailing, boat rental Naxos

Paroikia Marina, Paros

The most popular marina is in Paros. It can accommodate yachts up to 60 metres. They also offer refuelling, boat service and electricity. The city’s sights, the best hotels and apartments, as well as great taverns and bars, await visitors near the marina. The depth of the marina is 3.5 metres. Paros sailing, boat hire Paros, catamaran charter Paros, rent a motorboat Paros, rent a luxury yacht Paros, sailing charter Paros

Katapola port (Amorgos)

Katapola is the main port of Amorgos, located on the southeastern coast of the island.It is a natural bay with a picturesque setting, surrounded by hills and traditional white-washed buildings. Ferries and boats arrive and depart from Katapola, connecting Amorgos to other islands in the Cyclades, as well as the mainland of Greece. Amorgos sailing, boat rental Amorgos

Aegiali (Ormos)

Aegiali is the second-largest port on Amorgos, situated on the northern coast of the island. This port is closer to the village of Aegiali and is a key transportation hub for the northern part of Amorgos. Ferries operate from Aegiali, connecting Amorgos with other islands and the mainland.

Both ports in Amorgos are well-equipped to accommodate ferry traffic, and they provide essential services for visitors arriving by sea.

Tinos Marina, Tinos

This medium-sized marina locates in Tinos, a city of the same name as the island. The marina, which is 5.5 metres deep, can be moored by yachts up to 60 metres long, for which it offers many services. From here you can easily reach all the sights and beaches of the island.

Mykonos Marina, Mykonos

On the island of Mykonos, in the marina of the city with the same name as the island yachts up to 40 metres long can berth. Here 30 yachts can anchor at the same time. The water depth is 4.5 metres. In addition to restaurants, hotels, car rentals, and other services, there is also a boat service. Mykonos sailing,rent a boat Mykonos, bareboat charter Mykonos, luxury yacht charter Mykonos, catamaran rental Mykonos

Apollonia Marina, Naxos

It is a larger marina on the northeast coast of Naxos, in the town of the same name. It can accommodate boats up to 60 metres in length and a draft of 4 metres. The marina offers basic services. There are also some restaurants and bars. Naxos sailing, boat rental Naxos

Karavostasi Marina, Ios

It is a medium-sized marina on the island of Ios. It can accommodate boats up to 60 metres in length. The depth of the seabed is 4 metres. There are many services available such as a water tank refill, and you can find restaurants nearby.

Adamas Marina, Milos

The Adamas Marina can accommodate 50 boats up to 50 metres in length. The depth of the seabed is 5 metres. The offered services include bars, restaurants, boat maintenance service, and water tank refills. Milos sailing tour, Milos boat rental

Athinios Port

Santorini’s largest port is Athinios, located on the western side of the island. Locals also refer to it as New Port or Thira Port. It can accommodate hundreds of yachts. It is very well-equipped. There are drinking water, electricity and a refuelling station. The port is very busy, especially in the high season.

Skala Port

This is the old port, located near the town of Fira, the tourist centre of Santorini. It is small in size, so larger boats cannot berth here. The passengers of such boats are transported to the mainland by water taxi. You can reach the town by climbing 600 steps of stairs. You can go on foot, with a cable car or on the back of a donkey. If you get hungry, there are restaurants and taverns in the port. You can buy souvenirs and local delicacies in the smaller shops.

Ammoudi Port

The picturesque Ammoudi is on the northwestern coast of Santorini, next to Oia. It is only 13 km from Firas. The small port can accommodate yachts up to 20 metres in length. There are traditional fish taverns on the beach where you can try fresh seafood dishes and local delicacies as well.

Vlychada Port

Opened in 2008, Vlychada is Santorini’s most sheltered port. It can accommodate boats up to 25 metres in length. The depth of the seabed is 4 metres. There are drinking water, electricity and a refuelling station. In addition, there are bars and restaurants along the coast. Santorini sailing, yacht rental Santorini, rent a luxury yacht Santorini, catamaran rental Santorini

Sail in the Cyclades! The Cyclades sailing holidays

2-weeks The Cyclades sailing plan

We are going to provide you with a 2-week-long round trip. You can plan your trip flexibly, as the islands are located close to one another. You are going to leave from the marina of Lavrion in Athens and sail around the most important islands of the Cyclades in a clockwise direction.

Day 1: Athen (Lavrion Olympic Marina) – Kea

27.68 km (17.20 nm)
Sailing around the island of Makronisos from the south and from there a little northeast, you will arrive at the island of Kea. In addition to its sandy beaches, this place glories in many attractions. You will also find a medieval castle, churches, and watermills here. Fans of Greek mythologies and legends will also be amazed by this island. The ancient temples of Athens and Apollo, the holy sites of Demeter and Askiplios, and the famous Holy Theatre are also here.

Day 2: Kea – Kithnos

37.99 km (23.60 nm)
Kithnos is a typical Cycladic island, known to many tourists for its healing springs. If you love caves, you should check out the Katafiki, which operated as an iron mine until 1939. You can see beautiful stalactites and stalagmites as well as interesting rock formations here. If you are interested in the island’s past, you will also find a museum of local folklore and the Byzantine church museum in Dryopida. There are also many Cycladic-style churches on the island, the most popular of which is Panagia Kanala, the patron saint of the island.

Day 3: Kithnos – Sifnos

61.77 km (38.38 nm)
With the help of the Meltemi, you can get to the island of Sifnos in the southeast direction relatively quickly. On the way, you will pass west of the island of Serifos and then you will arrive in Sifnos. Here you can admire beautiful olive trees and almond fields. The symbol of the island is the Church of the Seven Martyrs, seen on a tiny peninsula-like extension of the east coast. Its beautiful whitewashed walls, sky-blue dome, and Cycladic architectural style are worth a look. In addition to the iconic church, the island hides many monasteries and museums. The most significant of these is the monastery of Chrissopighi.

Day 4.: Sifnos – Milos

43.65 km (27.12 nm)
Sailing southwest, you will reach the island of Milos. It is not too popular among tourists yet. On this beautiful volcanic island, you can enjoy nature and the atmosphere of ancient monuments, away from the crowds. In Adamas, the Agia Triada Church has a museum. The Mining Museum showcases minerals and the mining past of the island. The most important landmarks are the early Christian catacombs from the time of the Roman Empire. There is an ancient theatre nearby, where locals still hold events and theatre performances to this day. Read more about what to do in Milos

Day 5: Milos – Ios

86,09 km (53,49 nm)
Sailing east of Milos, you will arrive in Ios. It is a bustling island full of life. In summer, there are parties and festivals in the capital. If you want to get away from the city, discover the Tomb of Homer! If you want to see an archaeological excavation, visit the ruins of Skarkos!

Day 6: Ios – Thira (Santorini) – Kamari (Santorini)

68.56 km (42.60 nm)
The next destination is the island of Santorini. Your first stop is the port of Thira, south of Fira. You can go to the town on foot, in a cable car or on donkey back. In Fira, you will find yourself in front of the local archaeological museum where you can discover several ancient artefacts. The Gyzi Megaron Museum is at the northern end of the town. Here you can see the photographs taken before and after the 1956 earthquake. We recommend local restaurants. The town is famous for its wines and delicious gyros.

Your next stop is the town of Kamari on the eastern coast of the island. You can find several shops, pubs and restaurants in the streets close to the coast. There are cinemas on the island, one of them is an open-air cinema, surrounded by trees. Be sure to visit the beach that has Blue Flag Certification! You can go diving or try some exciting water sports. If you are interested in the ancient history of the island, visit the ruins of Thera on Mount Mesa Vouno in the south part of the island. Read more about what to do in Santorini

Day 7: Kamari (Santorini) – Iraklia

55.29 km (34.35 nm)
The island of Iraklia is among the most popular members of the Small Cyclades. Enjoy the natural beauty of this place! You can see monk seals and sea turtles on the shores! There are two villages on the island. One of them is Agios Georgios, moor your boat here. The capital of the island is Irakleia, located in the heart of the island

Day 8: Iraklia – Katapola (Amorgos)

36.86 km (22.90 nm)
Your next stop should be the elongated island of Amorgos to the south. The island has two main marinas. We recommend Katapola. There are many shops and bars in the streets near the marina. A walking path leads to the ruins of the ancient Minoan settlement at the nearby hill. From here, you will have a wonderful view of the bay. Read more about what to do in Amorgos, Amorgos sailing, or boat hire in Amorgos

Day 9: Katapola (Amorgos) – Apollonia (Naxos) – Naxos

70.08 km (43.54 nm)
After leaving Amorgos, take the time to explore the east coast of Naxos. The city of Apollonia is a perfect starting point. There are many restaurants and bars next to the marina, and you can visit some gorgeous beaches. After that, visit the city of Naxos. If you have time to discover the city, visit the castle in Naxos, which has a great view of the sea! If you are craving something delicious, try one of the local restaurants. We recommend the potato specialities. The potatoes grown here are famous all over Greece. If you want to go on a hike, many trails are waiting for you. They all lead to an interesting landmark. Read more about what to do in Naxos, Naxos sailing, or boat hire in Naxos

Day 10: Naxos (Naxos ) – Parikia (Paros)

28.45 km (17.68 nm)
The next destination should be Paros, the closest neighbour of Naxos from the west. The bay of Parikia is very well protected against both Meltemi and Sirocco; its disadvantage is its difficult accessibility. Even as an experienced sailor, it is not easy to moor here: in the west, some cliffs make it difficult to set in. The island itself is famous for its beautiful snow-white marble architecture. You should see the Frankish castle built-in 1260, which has now become part of the city of Parikia. If you are curious about the origins of the abundance of marble, be sure to check out the marble quarries that have been in operation for thousands of years.

As a sailor, the Skorpios Museum in Aliki is a must-see, where you can visit Benetos Skiadas ’wonderful collection of ship models. Be sure to check out the Valley of Butterflies, where you can see plenty of butterflies worthy of its name in a beautiful natural environment. Read more about what to do in Paros, Paros sailing, or Paros yacht charter

Day 11: Parikia (Paros) – Mykonos

47.04 km (29.23 nm)
Your next stop should be Mykonos, entertaining without limits! Do you want a real outdoor sea party? Don’t miss Super Paradise Beach, where guests are invited to party with loud music. If, on the other hand, you are looking for a quiet, peaceful stretch of beach, we recommend the lesser-known Panormos beach on the north side of the island. The family-friendly Platys Gialos beach with lots of hotels can be another excellent choice. Must-see attractions are the windmills found in several places on the island. Also be sure to visit the Little Venice district, where the buildings are located right next to the sea. Read more about what to do in Mykonos

Day 12: Mykonos – Tinos

17.30 km (10.75 nm)
Everywhere on the island of Tinos, you can see pigeonholes with a beautiful design similar to fortifications, a significant part of which is still in use today. In some small villages, even when houses were built, pigeonholes were patterned. You should visit the museum opened in his birthplace in memory of the sculptor Yannoulis Chalepas. Another important attraction is the Holy Trinity Monastery in Tinos.

Day 13: Tinos – Siros

22.55 km (14.01 nm)
The island of Siros is also a must-see sight! It has a buzzing nightlife, and one of the Greek casinos can also be found here. Mooring in Ermoupolis, you are already lost in the hustle and bustle of a relatively densely populated city. You can admire kaleidoscopic cottages, narrow alleys, and beautiful Orthodox churches during your stay. Read about what to do in Syros, Syros sailing or Syros yacht charter

Day 14: Siros – Makronisos – Athen (Lavrion-i Olympic Marina)

93.29 km (57.97 nm)
On the last day of your trip, you will make a longer trip towards the west and return to the marina of Lavrion. On your way, you can visit the long island of Makronisos. It was a prison island in the first part of the 20th century; today it is uninhabited. There are some quiet and peaceful beaches on the eastern coast. These are perfect for taking a nice break before the last section of your journey.

Finally, you return to Lavrion where you begin your adventure two weeks ago. If you are hungry, you can choose from a bunch of great restaurants near the marina. There are two interesting museums worth visiting in the little town: they exhibit minerals in one of them, while the other offers a remarkable collection of archaeological findings.

7 Days The Cyclades sailing tour

You will be navigating counter-clockwise during this trip, during which you can visit the central and southwestern parts of the Cyclades. Leave from Mykonos – known as a party capital – towards the west, and visit Milos on the way. You will then turn backwards and navigate to Paros, your final destination.
Day 1. Mykonos – Tinos 17.62 km (10.95 nm), Day 2. Tinos – Siros 22.05 km (13.70 nm), Day 3. Siros – Kithnos 67.88 km (42.18 nm), Day 4. Kithnos – Serifos 41.65 km (25.88 nm), Day 5. Serifos – Milos 50.59 km (31.43 nm), Day 6. Milos – Sifnos 42.31 km (26.29 nm), Day 7. Sifnos – Antiparos – Paros 65.97 km (40.99 nm)

Marine gas and boat gas stations in the Cyclades

• Olympic Marina, Athens: Depth: 10m, Working time: 0-24, GPS Coordinates: 37.6958441, 24.0583429
• Merihas, Kithnos: Depth: 8m, Working time: 0-24, GPS Coordinates: 37.389860, 24.397059
• Mikonos Marina, Mikonos: Depth: 4.5m, Working time: 0-24, GPS Coordinates: 37.4475266, 25.3275272
• Tinos, Tinos: Depth: 5.5m, Working time: 0-24, GPS Coordinates: 37.537555, 25.161119
• Parikia, Paros: Depth: 3.5m, Working time: 0-24, GPS Coordinates: 37.087424, 25.151587
• Naxos, Naxos: Depth: 5m, Working time: 0-24, GPS Coordinates: 37.106213, 25.372575
• Riva Tirasia, Santorini: Depth: 5m, Working time: 0-24, GPS Coordinates: 36.452705, 25.344247
• Thira New Port, Santorini: Depth: 4.5m, Working time: 0-24, GPS Coordinates: 36.386354, 25.428268
• Adamantas Milos, Milos: Depth: 5m, Working time: 0-24, GPS Coordinates: 36.721797, 24.444774

The Cyclades offer countless adventures and endless entertainment opportunities – each island is unique, so all of them are definitely worth visiting. As one single trip would not be enough for that accomplishment, we recommend that you spend several holidays in the area and explore something new each time!
Find more Cyclades sailing destinations, bareboat yacht charter Greece