Difficulty Level

SailingswimmingArchaeological sitescultureChurches-monasterieseco-friendly

Cyclades Islands Luxury Sailing Adventure (Catamaran)

Surrender to your dreams of sailing through the renowned enchanting Greek islands on this superb Sailing Adventure to the Cyclades Islands! Immerse yourself in the beauty of the Mediterranean, as you cruise on turquoise waters, exploring the magic of ancient sites and the charm of traditional Cycladic villages. Bask in the warm sun, taste fresh Greek food and absorb the rich culture that permeates these iconic islands. This eight-day sailing adventure, promises an unparalleled Greek island-hopping experience, unveiling the diverse character of each destination.

From laidback, non-touristy islands like Kythnos, Serifos and Kimolos to the aristocratic island of Sifnos and the volcanic island of Milos, renowned worldwide for its breathtaking beaches, your adventure encompasses the best of the Cyclades archipelago. Navigate through the crystal clear Aegean Sea, discovering the postcard-perfect, whitewashed villages and sapphire waters of Greece. Enjoy swimming in secluded beaches, inaccessible by car and bliss out on board with your fellow sailing buddies!

Whether you are a couple seeking a romantic gateway or a group of friends or family looking for quality time together, while sailing and exploring the Cyclades Islands, this is the perfect holiday for you.

Tour Highlights:

  • Sail across the Aegean sea and explore the hidden gems of the Cyclades islands on a catamaran yacht.
  • Walk up the trail to Serifos Town and enjoy the panoramic views it offers.
  • Enjoy the tranquility of the non-touristic and genuinely authentic Kimolos island.
  • Explore the volcanic island of Milos, one of the most impressive islands in Greece, where Venus de Milo was discovered.
  • Sail to the worldwide famous coves of Kleftiko and witness with your own eyes the striking rock formations, its emerald green waters and caves eroded by the sea.
  • Swim in secluded beaches and turquoise crystal clear waters at the uninhabited island of Polyegos, accessible only by private yacht.
  • Walk around the traditional settlement of Kastro in Sifnos island and enjoy the breathtaking views over the Aegean Sea.
  • Delight yourself in the delicious local cuisine and hospitality of the locals.

*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! Contact us to enquire more info about our private sailing experiences.

Additional information

Tour paceLeisure
Suitable forAll travelers, Couples, Families
Comfort levelSuperior



Day 1: Athens – Cape Sounio / Kythnos island

Welcome aboard! On our first day, you will embark our boat, which will serve as your vacation home for the next week (check in around 15:30 – 17:00pm). Upon arrival, you will participate in a boat tour, receiving all the necessary instructions, meet your fellow sailing companions and settle in your cabins. We will then sail towards Cape Sounio, where we will drop anchor and spend the night gazing at the impressive Temple of Poseidon, situated at the southernmost tip of the Attica peninsula (≈ 23nm, ≈ 3.5 hrs sailing).

If we start our journey from Lavrio port instead of Alimos marina, we can even make it to Kythnos island on day 1 (≈ 32nm, ≈ 4.5 hrs sailing). If this case, the first port of call will be Loutra, translated as “baths” due to the presence of hot springs. Don’t miss the opportunity to enjoy a revitalizing evening swim at the warm waters! At night, you can enjoy dinner at one of the seaside restaurants and savor the local cuisine.
Tip: Sfougata (similar to cheese bites with local cheese) is a must-try!

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


Day 2: Cape Sounio/ Kythnos island - Serifos island

What could be better than a morning dive from the boat, beneath the imposing temple of Poseidon, even before enjoying breakfast? Following breakfast on board, we will set our compasses towards the enchanting island of Serifos, inviting you to immerse yourself in the sought-after Cycladic simplicity that defines this destination.

If our starting point is Kythnos, consider joining us on a morning hike before we set sail to the unspoiled and charming island of Serifos (≈ 44nm, ≈ 6 hrs sailing).

Upon reaching the port, we invite to accompany us to an uphill walk all the way to Chora, the main town of the island. It is a steep, yet short ascent, and the views, especially from the Venetian Fortress, will captivate your senses! Wander through the narrow streets and lose yourself in the charm of Chora! Enjoy your dinner in one of the traditional tavernas and perhaps indulge in some drinks afterwards at one of the many stylish bars.

meals Breakfast, Lunch                 accommodation Cabin on board the sailing yacht


Day 3: Serifos - Kimolos island

Today’s journey unfolds as we sail towards one of the least touristic and possibly most authentic islands of the Cyclades, Kimolos (≈ 21nm, ≈ 3hrs sailing). Kimolos, a volcanic island, derives its name from the greek word “kimolia”, meaning chalk. This secluded haven is ideal for those looking to escape the crowds and enjoy peacefulness and tranquility, amidst stunning white sandy beaches and tiny villages.

We will spend the day anchored at one of its pristine beaches, chosen based on weather conditions. Later, before reaching the port, you will have time to take a walk to Chora, the main town, and explore its narrow, cobbled streets and locally run restaurants and bars.

meals Breakfast                   accommodation Cabin on board the sailing yacht


Day 4: Kimolos – Polyegos island – Milos island

Right opposite Kimolos lies the small uninhabited island of Polyegos, a secluded paradise with captivating turquoise crystal-clear waters. This will serve as our first swimming stop for today, offering you a chance to enjoy swimming, snorkeling, boat dives, or simply unwind on the deck and back in the sun.

Next, we will sail along the southern coastline of Milos to reach the spectacular coves of Kleftiko – arguably the most photographed beach on Milos, and for a rightfully so! Kleftiko, a former pirates’ hideout, boasts impressive volcanic rock formations, countless caves and turquoise crystal-clear waters, accessible solely by boat or on foot via a hiking trail.

There will be ample time for swimming, exploring the numerous caves and enjoying lunch on board before we sail towards the port of Milos, where we will anchor for the night (total distance for today ≈ 33nm, ≈ 4.5 – 5 hrs sailing).

meals Breakfast, Lunch                     accommodation Cabin on board the sailing yacht


Day 5: Milos - Sifnos island

Following breakfast on board, we invite you to join a morning tour exploring more of Milos’ highlights, including the moonscape-like Sarakiniko beach, the 2nd most well-known landmark after Kleftiko, the catacombs, the site where Venus de Milo was discovered, the ancient theatre and the picturesque fishing village of Klima with its colorful postcard –like houses (tour duration approx. 3hrs, at an extra cost).

Bid farewell to Milos as we hoist the sails toward our next destination, the charming and aristocratic island of Sifnos (≈ 20 – 24 nm, ≈ 3 – 4 hrs sailing). The exact marina or spot where we will spend this evening will depend on the weather conditions.

Once in Sifnos, seize the opportunity to visit the traditional and historic settlement of Kastro, a captivating cliff-top village that literally means Castle. Built atop the ruins of the island’s ancient capital, Kastro exudes a strong medieval character and offers breathtaking panoramic views over the Aegean sea!

meals Breakfast                          accommodation Cabin on board the sailing yacht


Day 6: Sifnos - Kythnos island

After breakfast, we’ll set sail for Kythnos island, another hidden gem of the Cyclades that has preserved its authentic character (≈ 38nm, ≈ 5 – 5.5 hrs sailing).

A visit to Kythnos is incomplete without going to the unique beach of Kolona, one of the island’s landmarks! Kolona is a sand strip connecting Kythnos with the islet of Agios Loukas, creating a landscape of unparalleled beauty! Once there, you can enjoy swimming, snorkeling, and a delightful lunch at the only tavern on the beach. We also invite you join us for a walk to the summit of Agios Loukas islet and enjoy the panoramic views of the surroundings.

Later, we will head to Merichas, the main port of Kythnos, where we will spend the evening. Alternatively, if you prefer, we can spend the final night before returning to Athens anchored at a secluded beach, gazing at the stars and savoring all the tranquility our sailing yacht can offer.

meals Breakfast                               accommodation Cabin on board the sailing yacht


Day 7: Kythnos - Athens

After breakfast, we will begin our sailing trip back to Athens (≈ 50nm, ≈ 6.5 – 7 hrs sailing). En route, we will make a stop to enjoy a final swim, accompanied by lunch prepared by our crew on board, before reaching Athens. Tonight, you will spend your evening in the marina in Athens, which offers you the opportunity to explore the south suburbs of the city, take a seaside stroll, and dine in one of the seaside restaurants.

meals Breakfast, Lunch                           accommodation Cabin on board the sailing yacht


Day 8: Departures - Check out

In the morning, by 9:00am, it’s time to check out from the boat. You can arrange a transfer to the airport if you need to catch your flight, or continue your holidays in Greece! If needed, we can assist in arranging transfers for your convenience.

meals On your own                                accommodation On your own

*Skipper & crew reserve the right to modify the itinerary based on the weather and wind conditions at their discretion.

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).
All walks and hikes, as indicated in the tour itinerary.
Port taxes, petrol, all electricity and water port costs
1 set of Bed linen and towels per person.
Cleaning fee.
VAT, Yacht and Liability insurance.

What is not included :

International airfares.

Travel insurance.

Any meals not included above.

Optional activities that are not included in the day-to-day itinerary.

Security deposit 300 euro per person (cash during check in), fully refundable upon disembarkation

Transfer to/from the marina and hotel/airport transfers

Other expenses of personal nature and tips

Scheduled departures 2024:

Departs on Price / person +Own Cabin
22 June ‘24 2,450 € 1,350 €
6 July ‘24 2,450 € 1,350 €
7 September ‘24 2,450 € 1,350 €
21 September ‘24 2,300 € 1,200 €

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

Prices for private groups 2024:

Prices per person
Number of guests Period A Period B Period C Period D Period E
4 guests 2,300 € 2,560 € 2,800 € 2,930 € 3,080 €
5 guests 2,050 € 2,320 € 2,420 € 2,680 € 2,850 €
6-7 guests 1,770 € 1,970 € 2,060 € 2,280 € 2,470 €
8 guests 1,580 € 1,670 € 1,800 € 1,980 € 2,190 €
Period A before 27/04 & after 19/10
Period B 27/04-25/05 & 28/09-19/10
Period C 25/05-15/06 & 14/09 -28/09
Period D 15/06-27/07 & 24/08-14/09
Period E 27/07-24/08

Please read carefully our booking terms & conditions.

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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