Difficulty Level

SailingswimmingArchaeological sitescultureChurches-monasterieseco-friendly

Cyclades islands Luxury Sailing Adventure (Catamaran)

Surrender to your dreams of sailing the renowned Greek islands on this superb sailing adventure to the Cyclades islands! Sail on a catamaran yacht in 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,  Serifos and Kimolos to the aristocratic island of Sifnos and the volcanic island of Milos, renown worldwide for its spectacular beaches, 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!

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 Kimolos island, whose name derives from the Greek word for chalk
  • 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 boat
  • Walk around the traditional settlement of Kastro in Sifnos island and enjoy the magnificent 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 be your vacation home for the next week (check in around 15:30-17:00pm). You will take a boat tour with all the necessary instructions you need to know, meet your fellow sailing companions and settle in your cabins. We will then sail towards Cape Sounio, where we will throw our anchor and spend the night gazing at the stars and the impressive Temple of Poseidon, located at the southernmost tip of the Attica peninsula (≈ 23 nm, ≈ 3 – 3.5 hrs sailing).

In case we start from Lavrio port, instead of Alimos marina, we can even make it to Kythnos island on day 1 (≈ 32nm, ≈ 4.5 hrs sailing). If so, 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: Cape Sounio/ Kythnos island - Serifos island

What better than a morning dive from the boat, under the imposing temple of Poseidon, before even taking breakfast?! After breakfast on board, we will set our compasses with direction the island of Serifos, where you can find the Cycladic simplicity you might be looking for.

In case we are in Kythnos, we can take you on a morning hike, before setting sails to the unspoiled and charming island of Serifos (≈ 44nm, ≈ 6 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, Lunch                 accommodation Cabin on board the sailing yacht


Day 3: Serifos - Kimolos island

Today we will sail towards one of the least touristic and most authentic Cycladic islands, Kimolos (≈ 21nm, ≈ 3 hrs sailing). Kimolos is another volcanic island, whose name derives from the Greek word “kimolia”, which is translated into chank. The island is the perfect getaway for those looking to escape the crowds and enjoy peacefulness and tranquility, among some spectacular white sandy beaches and tiny villages.

We will spend the day anchored at one of its pristine beaches (depending on the weather), before reaching the port, from where you can walk to Chora, the main town, 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 turquoise crystal clear waters that will definitely captivate your senses. This will be our first swimming stop for today. You will have time to enjoy swimming, snorkeling, dives from the boat or simply relax on the deck and sip the sun.

We will then sail along the south coastline of Milos to reach the spectacular coves of Kleftiko, probably the most photographed beach of Milos and for a reason! Kleftiko is a former pirates’ hideout with imposing volcanic rock formations, countless caves and turquoise crystal clear waters, accessible only by boat or on foot via a hiking trail.

There will be time for swimming, exploring the numerous caves and enjoying lunch on board, before sailing towards the port of Milos, where we will spend the night.

meals Breakfast, Lunch                     accommodation Cabin on board the sailing yacht


Day 5: Milos - Sifnos island

After breakfast on board, we can take you on a morning tour around the island and show you some more of Milos’ highlights, such as the moonscape-like Sarakiniko beach, the 2nd most well-known landmark after Kleftiko, the catacombs, the place 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).

We can then say goodbye to Milos and set sails to our next destination, the charming and aristocratic island of Sifnos (≈ 20 – 24 nm, ≈ 3 – 4 hrs sailing). The exact spot/marina where we will spend this evening depends on the weather conditions.

Once in Sifnos, do not miss the chance to visit the traditional and historic settlement of Kastro, a lovely cliff-top village, which literally means Castle. Kastro is built on top of the ruins of the ancient capital of the island, it has a strong medieval character and it offers spectacular 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 sails  to Kythnos island, another hidden gem of the Cyclades that has managed to maintain its authentic character (≈ 38nm, ≈ 5 – 5.5 hrs sailing).

You cannot visit Kythnos, without going to the unique beach of Kolona, one of the island’s landmarks! Kolona 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. We also invite you to walk with us all the way up on top of Agios Loukas islet and enjoy the panoramic views it offers.

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

meals Breakfast                               accommodation Cabin on board the sailing yacht


Day 7: Kythnos - Athens

After breakfast, we’ll set on our sailing trip back to Athens (≈ 50nm, ≈ 6.5 – 7 hrs sailing). We will make a stop en route to enjoy a last swim, as well as lunch on board prepared by our crew, before we reach Athens. Tonight you will spend your evening in the marina in Athens, which gives you the chance to explore a bit the south suburbs of the city, go for a seaside walk and have dinner 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, 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

*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 program
Snorkeling equipment (not 100% sure, depends on covid-19 restrictions)
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

Security deposit 200 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 2023:

Departs on Price / person +Own Cabin
27 May ’23 1.950 € 900 €
17 June ’23 2.050 € 1.000 €
01 July ’23 2.050 € 1.000 €
02 Sept ’23 2.050 € 1.000 €
23 September ’23 1.950 € 900 €

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

Prices for private groups 2023:

Prices per person
Number of guests Period A Period B Period C Period D
4 guests 2.340 € 2.420 € 2.610 € 2.740 €
5 guests 2.010 € 2.040 € 2.220 € 2.260 €
6-7 guests 1.720 € 1.750 € 1.900 € 1.980 €
8 guests 1.440 € 1.540 € 1.700 € 1.830 €
Own cabin 800 € 900 € 1.000 € 1.150 €
Period A before 20/05 & after 7/10
Period B 20/05-17/06 & 16/09-7/10
Period C 17/06-29/07 & 02/09 -16/09
Period D 29/07 – 02/09

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!

Leave a Review