Difficulty Level

SailingswimmingArchaeological sitescultureChurches-monasterieseco-friendly

Cyclades islands Sailing Adventure

Surrender to your dreams of sailing the renowned Greek islands on this superb sailing adventure to the Cyclades islands! Sail on Mediterranean waters, swim in turquoise seas, explore ancient sites and traditional Cycladic villages and soak up the sun, fresh Greek food and culture. From laidback, non-touristy islands like Kythnos and Serifos to the cosmopolitan islands of Mykonos and Paros, experience the utmost of Greek island hopping on this eight-day sailing odyssey.
Explore the whitewashed villages and sapphire waters of Greece, sail across the Aegean Sea, visit some of the picture-postcard Cyclades islands, enjoy swimming in secluded beaches, inaccessible by car and bliss out on board with your fellow sailing buddies!
Whether you are a couple, group of friends or family, this is the perfect holiday for you if you like sailing and you wish to explore the utmost of the Cyclades islands!

Tours Highlights

  • Sail across the Aegean sea and explore the renowned Cyclades islands
  • Hike to the Castle of Orias on Kythnos island and to Vryokastro, the island’s ancient capital
  • Visit Syros island, the Duchess of the Aegean
  • Enjoy the vibrant nightlife of Mykonos & stroll around the little Venice of Greece
  • Visit the UNESCO protected island of Delos, one of the most important archaeological sites in Greece
  • Swim in secluded beaches and turquoise crystal clear waters
  • Enjoy water sports or other outdoor activities on Paros island
  • Walk up the trail to Serifos town and enjoy the panoramic views it offers
  • Delight yourself in the delicious local cuisine

*This is a semi-private sailing holiday, operated in small groups of 8-10 guests. Guests have their own cabins, but you might share the WC with your co-travelers, as well as common areas on the yacht (living room, kitchen, deck etc). In case you wish to enjoy a 100% exclusive experience, having the entire yacht available just for you, your family and friends, we welcome you to book a private sailing holiday and enjoy the utmost of the Greek islands in an intimate way!

You can find more info about our private sailing experiences here.

Additional information

Tour paceModerate
Suitable forAll travelers, Couples, Families
Comfort levelStandard



Day 1: Athens – Kythnos island

Welcome aboard! On our first day, you will embark our boat, which will be your vacation home for the next week. You will take a boat tour with all the necessary instructions you need to know and you can settle in your cabins. We will then sail to our first destination, Kythnos Island, one of the less touristic and most authentic islands of the Cyclades (≈ 32nm, ≈ 4.5 hrs sailing).
First port of call will be Loutra, which is translated into baths, because of the hot springs there. Do not miss the chance to enjoy an evening revitalizing swim at the hot springs!
You can also enjoy dinner in one of the seaside restaurants and taste the local cuisine. Tip: sfougata (like cheese bites with local cheese) is a must!

meals Welcome snacks & drinks          accommodation Cabin on board the sailing yacht


Day 2: Hiking Kythnos - Syros island

After enjoying breakfast on board, we’ll head on a hike on Kythnos island. Starting right from the port, we will hike up hill to the northernmost tip of the island and visit the Castle of Oria, overlooking the Aegean Sea. This fortified acropolis was the capital of the island during the Byzantine times and the Latin occupation; but it seems that it had already been inhabited since prehistoric times. 100 chapels flourished there during the Venetian Rule, of which only two still stand today. After enjoying the panoramic views we’ll follow the same path down to return to the boat (Hike ≈ 2 ½ hours, easy to moderate difficulty level).
Alternatively, you may choose to hike from Loutra to Chora, the island’s capital and visit the beautiful small town, walk through its narrow alleys and enjoy an iced drink in one of the cute cafes.
In the afternoon, we’ll set sail to Syros island, having a stop for a swim en route (≈ 32nm, ≈ 4 hrs sailing). Once we reach the port, you cannot help but admire the beautiful, aristocratic town of Ermoupoli which is also the capital of the Cyclades islands. The Duchess of the Aegean blends perfectly the Cycladic minimalism with the medieval charm, the Orthodox with the Catholic worlds, and is waiting for you to explore it! Wonder around its winding alleys and see with your own eyes her impressive architecture, cultural wealth and irresistible combination of the Cycladic and Western influences unfold in front of your eyes!

meals Breakfast, Lunch                 accommodation Cabin on board the sailing yacht


Day 3: Syros – Mykonos island (optional visit of Delos archaeological site)

In the morning, we will depart from Syros with destination the worldwide renowned island of Mykonos (≈ 19nm, ≈ 2.5 hrs sailing). We will aim at having you there early, so you can have enough time to explore Greece’s most cosmopolitan island, a whitewashed paradise in the heart of the Cyclades. Set out on an exploration to discover a fascinating destination where glamour meets the Cycladic simplicity!
You will have the rest of the day free to experience Mykonos the way you wish. We, however, strongly recommend you to take a guided tour to Delos island, a UNESCO protected site and one of the most significant archaeological sites in Greece. Rates start from 50€ per person to join guided tours (including 20€ pp boat service to/from Delos, entrance fees & archaeological guide), but depending on the number of people interested in your group, we could also arrange a private tour.
We can also offer a guided walking tour of Mykonos (approx. 3 hrs duration), so you can visit the major highlights of Chora and learn more about its history by a local!
If you love gastronomy and you want to learn more about the Greek cuisine, then we would recommend you to take a cooking class at a traditional Myconian house and find out some of the secrets of the Mediterranean cuisine! Enjoy afterwards your dinner escorted with wine and soft drinks and get free small bag of local products as a souvenir at the end.

meals Breakfast                   accommodation Cabin on board the sailing yacht


Day 4: Mykonos – Rinia island – Paros island

Right opposite Delos lies the tiny uninhabited island of Rinia, a secluded paradise with turquoise crystal clear waters. This will be our first stop for today. You will have plenty of time to enjoy swimming, snorkeling, dives from the boat or simply relax on the deck and sip the sun.

We will then set sails for Paros island and in particular the small quaint fishing town of Naousa (≈ 25nm, ≈ 3 – 3.5 hrs sailing). On our way there we can make another stop for a swim at the beach of Kolimbithres with its unique rock formations.

Once in Naoussa, you can walk through its narrow alleys, visit the old port and the Venetian fortress. There are several optional activities that we can organize for you, such as horse riding, wine tour & tasting, hiking or  sea kayak! It only depends on your preferences and mood and you can consult your tour guide for any of these activities you could enjoy while on the island.

meals Breakfast, Lunch                     accommodation Cabin on board the sailing yacht


Day 5: Paros - Antiparos - Serifos island

Today, after breakfast we’ll sail to Antiparos island, just a few miles away. You can enjoy swimming and snorkeling in one of the island’s secluded beaches, before we set sails to the unspoiled and charming island of Serifos (≈ 25nm, ≈ 3 – 3.5 hrs sailing).
Once we reach the port, we welcome you to walk with us uphill all the way to Chora, the main town of the island. It is a steep, yet short walk up and the views, especially from the Venetian fortress will captivate your senses! Stroll through the narrow streets and get lost in Chora! Enjoy your dinner in one of the traditional tavernas and why not, some drinks afterwards in one of the fancy bars.

meals Breakfast                          accommodation Cabin on board the sailing yacht


Day 6: Serifos - Kythnos island (different port)

After breakfast, we’ll set sail back to Kythnos island, however this time we will dock at the main port, Merichas (≈ 23nm, ≈ 3 hrs sailing).
Upon arrival in Merichas, you can join us on a hiking trail through the island’s ancient history! Starting right from Merichas, we’ll hike towards Vryokastro, the island’s ancient capital and then to the probably most stunning beach of the island, Kolona! A short hike up will take us to the hill of Vryokastro, a currently abandoned archaeological site and one of the most important prehistoric settlements in the Aegean. Archaeological research has brought to light findings dating back to the Mesolithic Age.
Afterwards, we’ll descend to the white sandy beach of Apokrousi, where we’ll make a stop to relax and swim. Next comes one of the island’s highlights, the unique beach of Kolona. It is actually a strip of sand joining Kythnos with the islet of Agios Loukas, creating a landscape of unparallel beauty! Once there, you can enjoy swimming and snorkeling, as well as lunch at the only tavern on the beach (if open) or snack lunch. You will later be transferred back to the port. (Total Hike Duration: 3 hours / 4-5 hours incl. stops | Total Distance: ≈ 5.5 – 6.5 km).
You can enjoy your dinner in one of the local tavernas in Merichas or grab a taxi and head to the picturesque Chora, the capital of the island.

meals Breakfast                               accommodation Cabin on board the sailing yacht


Day 7: Kythnos - Athens

After breakfast, we’ll set on our sailing trip back to Lavrio marina, in Athens (≈ 32nm, ≈ 4.5 hrs sailing). We will make a stop en route for swimming (probably near Cape Sounio, gazing at the spectacular Temple of Poseidon) and lunch on board prepared by our crew, before we reach Athens.

meals Breakfast, Lunch                           accommodation Cabin on board the sailing yacht


Day 8: Departures - Check out

In the morning, by 9:30am – 10:00am, you will have to check out from the boat. You can either arrange a transfer to the airport, if you need to catch your flight, or continue your holidays in Greece!

meals On your own                     accommodation On your own

What is included:
 Sailboat with skipper and tour leader
All meals as indicated on the trip notes (welcome snacks on day 1, 6 breakfasts, 3 lunches)
Hiking tours on Kythnos (day 1 & 6) and Serifos island (optional, for those who want to join)
 Snorkeling equipment
Port taxes, petrol, all electricity and water port costs
 Bed linen and towels
Cleaning fee
VAT, Yacht and Liability insurance

What is not included :

International airfares

Travel insurance

Optional activities that are not included in the day-to-day itinerary (guided tour in Delos, cooking class in Mykonos, optional activities in Paros etc)

Security deposit (TBA depending on the yacht)

Transfer to/from the marina and hotel/airport transfers

Other expenses of personal nature and tips

Scheduled departures 2021 & 2022

Departs on Price / person +Own Cabin
05 June ‘21 1,350 € 580 €
10 July ‘21 1,415 € 620 €
24 July ‘21 1,415 € 620 €
04 September ‘21 1,415 € 620 €
25 September ‘21 1,350 € 580 €
04 June ‘22 1,350 € 580 €
02 July ‘22 1,415 € 620 €
10 September ‘22 1,415 € 620 €
08 October ‘22 1,250 € 580 €

*There is a minimum of 5 participants for our scheduled sailing trips to depart

Prices for private groups 2021 – 2022:

Yacht class Price per group (up to 4 guests)
Period A Period B Period C Period D
Economy monohul 6,220 € 6,400 € 6,700 € 7,000 €
Prestige monohul 6,950 € 7,620 € 7,950 € 8,450 €
Economy Catamaran 7,200 € 7,920 € 8,220 € 8,950 €
Prestige Catamaran 7,700 € 8,550 € 9,000 € 9,850 €
 Yacht class Extra cost per person (5-8 guests)
Period A Period B Period C Period D
Economy monohul 500 € 500 € 520 € 520 €
Prestige monohul 600 € 650 € 700 € 750 €
Economy Catamaran 650 € 700 € 800 € 880 €
Prestige Catamaran 750 € 800 € 900 € 1,000 €
Period A before 22/5 & after 2/10
Period B 22/5-26/6 & 18/9-2/10
Period C 26/6-31/7 & 21/8-18/9
Period D 31/7 – 21/8

Please read carefully our Updated Flexible Terms & Conditions.

Travel safe – Learn more about our enhanced safety measures.

Tour Reviews

5/5 based on 1 review
June 26, 2019

AMAZING! Thanks Danae + Costas for an incredible week sailing the Cyclades
We just spent the most amazing week sailing the Cyclades Islands with Danae and Costas, and could not recommend it more. Danae was the most wonderful guide from beginning to end – quick and accommodating on email, she made the booking process easy, and then was fun, warm and knowledgeable during the trip itself. Costas was a wonderful skipper and we felt very safe and well-looked after between the two of them – we can’t wait to go on another trip with the two of them!

We were four friends on a private trip, which meant we had quite a lot of flexibility during the trip around where we went and what experiences we wanted. We were after small ports, long swimming sessions and cultural experiences, and Danae and Costas came up with a great itinerary that allowed us to spend a couple of nights outside of the ports, anchored in small, tranquil bays under the stars. We sailed when the wind made it possible and motored away when it was calm – you have to be aware of what the winds will let you do, but we were lucky to get a variety of windy days for sailing and quiet days that were perfect for swimming. Danae has such a varied knowledge of Greece that I’m sure she could come up with a great itinerary for any type of trip you wanted – and her English is impeccable, so you’ll find it easy to communicate exactly what you’re after,

The breakfasts and lunches were fresh and delicious, and we went to small tavernas on different islands each night we were in ports, and then bought food for our own dinners on the boat the nights we were outside of port.

Our route included:
Athens (Lavrio) – Kythnos (port) – Serifos (port) – via Poliegos (swim) – Kimolos (anchor) – via Poligeos (swim) – Sifnos (anchor) – Kythnos (port) – Athens Rafina (port)

We had some of the best swims of our life, in gorgeous blue water, alongside white cliffs and in caves and beside small churches. It was a dream and made all the better for Danae and Costas’ unwavering friendly, calm and professional attitudes. I could not recommend this trip more – if you’re trying to decide how long to go for, double what you’re thinking and book it right away!

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