Sailing the Cyclades is a unique way of exploring the most beautiful islands in Greece. Whether you are a sailing enthusiast or this is your first time on a sailboat, the Cyclades islands offer an idyllic and diverse sailing experience. The 1-week sailing in the Cyclades itinerary below will take you to some of the most beautiful and secluded spots around these Greek islands.
The Cyclades are a group of islands in the Aegean Sea which home some of the most important Greek ruins, such as Akrotiri in Santorini or the Temple of Apollo in Naxos. The islands are famous for their stunning beaches and are a popular destination for sun seekers. The Cyclades have roughed terrain but also some of the most beautiful Greek villages, with white houses and churches with blue domes overlooking the sea.
With crystal-clear waters, snow-white beaches, and charming villages, this route is sure to leave you with memories of a lifetime. So grab your sailing jacket and sunglasses, and let’s set sail!
Sailing The Cyclades: The Best 7 Day Itinerary
This 1 week sailing the Cyclades guide includes some of the most popular and well-known tourist destinations, along with some hidden gems that are only easily reached by sailboat.
During the summer months, from around June to September, you should be aware of the Meltemi winds. These winds blow from the north and can reach up to 50knts. They will often blow from a week at a time.
They are well forecasted so make sure you download the best sailing apps for the area before you arrive. This itinerary is designed to take these winds into account.
Day 1: Santorini
Start your sailing adventure on the beautiful island of Santorini. There are several reasons why Santorini is the best place to hire your charter boat from.
The first and obvious reason is that Santorini has a major airport so it is easily reached at any time of the year. It is also well connected by sea, with regular ferries from a number of islands and from the mainland.
The second reason is that Santorini is a must-visit island in the Cyclades, but it isn’t well set up for sailors. There are very few anchorages and the marinas get booked up months in advance. By starting your trip here you will have a chance to explore before leaving the harbour and again when returning, without any of the hassles of booking a space or trying to find a well-protected anchorage.
Finally we would advise starting your trip here is down to the predominant winds. With the Meltemi blowing from the north it’s better to begin your journey beating into the wind, so that you can be sure of a pleasant downwind sail back even if the Meltemi starts to blow.
Where to Visit in Santorini
– Explore the beautiful capital of Fira, with its famous white buildings and blue domed churches.
– Visit Oia for stunning sunset views and picturesque streets lined with shops and cafes.
– Take a dip in the hot springs at Palea Kameni or explore the volcanic island by boat.
– Sample delicious local wines at one of Santorini’s many vineyards.
– Enjoy the local Santorini food which uses ingredients grown on the island such as tomatoes and white aubergines.
– For more things to do in Santorini, check out my itinerary for the island, by clicking here.
Day 2: Ios
After a night in Santorini, set sail for the nearby island of Ios. This small island may not be as well known as its neighbours, but it has some hidden gems waiting to be discovered. Paralia Bay on the south of the island is a great anchorage to shelter in from northerly winds, and the sandy beach there is beautiful.
If you’re looking for night life and seafood restaurants then head to the port of Ios on the west side of the island instead and enjoy a night out in this vibrant town.
Where to Visit in Ios
– Hike up to the viewpoint at Skarkos for panoramic views over the island.
– Visit the tomb of Homer, believed by many to be the final resting place of the famous poet.
– Explore Chora, the charming main town of Ios with its winding cobbled streets and traditional Greek architecture.
– Spend a day lounging on Mylopotos beach or sail to other nearby beaches like Manganari or Kalamos.
Day 3: Schoinousa
After Ios, continue sailing east to the small and peaceful island of Schoinousa. The island’s several anchorages offer perfect shelter from all winds, with crystal-clear water for swimming and snorkelling.
Some people call Schoinousa the undiscovered Santorini, and it certainly has that feel about it. With its pretty little backstreets and white-washed houses you could spend all afternoon sitting in a taverna here and watching the world go by (slowly!) Without all the crowds you will feel as though you’re one of the locals.
Where to Visit in Schoinousa
– Explore the charming main village of Chora and sample some delicious local food at one of the tavernas.
– Hike to a deserted beach on the south coast or sail around the island to visit other secluded beaches like Kato Koufonisi or Psili Ammos.
– Take a dip in the natural spring at Agia Anna or visit the church nearby for panoramic views over the island.
Day 4: Naxos
From Schoinousa, sail northeast to the largest island in the Cyclades, Naxos. It’s well-protected ports make it a great choice for sailors, and with its ancient sites and beautiful beaches there is plenty to see and do here.
On the western side of the island lies Naxos Town which is a great place to base yourself. There is also a well equipped marina here if you’re out of water! Here you can spend a day wandering through marble-paved streets and exploring Ancient ruins like Portara, the giant marble gate left behind by 6th century BC builders.
Where to Visit in Naxos
– Take a hike up Mount Zas, the highest peak in the Cyclades islands at 1004m, for breathtaking views over Naxos and neighbouring islands on a clear day.
– Visit the ancient site of Apollon Temple in Flerio, believed to be one of the largest temples in Greece.
– Relax on a beach such as Agios Prokopios or Plaka, where you can also find watersports and activities like windsurfing and stand up paddle boarding.
Day 5: Paros
On day 5 sail the short hop west to the beautiful island of Paros. This is a bustling island with plenty going on, but it’s well worth visiting for its stunning beaches and iconic villages like Naousa with its Venetian harbour.
You can anchor right outside Naousa alongside the super yachts and vintage sailboats. The bay has protection from almost every wind angle depending on where you set hook in the large anchorage.
Where to Visit in Paros
– Visit Marpissa village for stunning traditional architecture and a taste of local life on the island.
– Relax on one of Paros’ many beaches such as Golden Beach or Pounda beach where you can also try out watersports like kitesurfing.
– Dine on the harbourfront and sample the freshly caught fish.
Day 6: Delos & Lefkes
On day 6 take a day trip from Paros to the nearby island of Delos, a UNESCO World Heritage site and one of the most important mythological, historical, and archaeological sites in Greece. The birthplace of Apollo and Artemis, it was once a bustling port before being abandoned in the 7th century AD.
In the afternoon you can start your sail back down south. Stop at the well-protected Tsoukalia Beach and spend the evening exploring the pretty ancient town of Lefkes.
Day 7: Return to Santorini
After a jam-packed week of sailing the Cyclades it’s time to head back to Santorini and return your charter boat. Hopefully you will have the winds on your side on this leg of the sail, and you should make excellent time.
Top Tips For Sailing The Cyclades
- As mentioned earlier, the predominant summer winds blow from the north. During the shoulder season and winter months keep an eye out for storms and high winds from the south.
- Most of the anchorages here have sandy bottoms. Make sure your sailboat has one of the best anchors for sand, and that it’s dug in well (especially when the Meltemi winds are forecast!)
- During the summer the Cyclades are hot, but because of the windier days the evenings can feel a little chilly. Bring a few warm layers for cooler nights on board.
- Greek food is delicious, so try to eat out at a local taverna at least once. Gyros, saganaki, Greek salads, and freshly caught seafood are some of the most popular choices.
Conclusion: Sailing The Cyclades
The Cyclades is one of Greece’s most challenging cruising grounds, but also one of its most rewarding. In exchange for some high winds, you will be greeted with the friendliest of people, the bluest waters, and the prettiest towns and villages. This is the sailing adventure of a lifetime in one of the best cruising grounds in the world.
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The Cyclades look like a dream! I’ve never been to Greece, but this is added to my itinerary when I get there! Saving for later.
Your pictures look great and this is a great itinerary. My parents were just there about a month ago and said it was amazing! I now need to put it on my list of places to visit.