One of the most famous archipelagos in the world, the Cyclades of Greece have way more to offer than pristine beaches, crystal clear waters and amazing sailing experiences. They are the cradle of over ten millennia of rich history, boast extreme geographical diversity, abundant marine wildlife and feature the best of traditional Aegean architecture and Mediterranean cuisine.

This sailing adventure goes far beyond mere island hopping, giving you a chance to explore way beyond each island’s marina, as well as immerse in local culture, savor the local flavors and learn a thing or two about the history of this immensely beautiful part of the world.

And did we mention that it provides you with the opportunity to actively engage yourself in sailing? Whether you have done it before or not, The Aegean archipelago, with its clear deep blue waters is the ideal place to get acquainted with the basics of sailing and our skippers are always happy to show you the ropes!

For sport enthusiasts we also advice an other active tour you may like:  Northwestern Greece Multi-Activity Adventure


2022/2023 pricing, please contact us for an estimate anytime

2020 Land Cost Per Person (double occupancy)

Price Per Person:

$ 2,220 ( based on a group of four)

  • Immerse in the rich culture, delicious cuisine and millennia spanning history of Athens, Greece
  • Explore over a dozen different beautiful sailing destinations, visiting six islands in the process
  • Swim then hike to the Temple of Poseidon at Cape Sounion
  • Enjoy the laid back atmosphere on the quiet island of Kythnos
  • Relax in a hot spring while looking at the Milky Way at the tiny fishing village of Loutra
  • Savor amazing Aegean seafood on the island of Sifnos
  • See unique geological formations and swim in turquoise waters on the volcanic island of Milos
  • Swim in turquoise waters by the uninhabited tiny island of Polyaigos and, if you’re lucky, spot a Mediterranean seal hunting for fish
  • Hike to the main town of Serifos and experience the “iron island’s” coffee culture

Price Includes:

  • Lodging accommodation
  • Air conditioned vehicle
  • English speaking guide service
  • Meals as mentioned
  • 1 bottle of water (0.5lt) per person per day
  • Transfers from/to airport
  • Additional hotel stays before and after the trip can be booked with us
  • Experienced English-speaking guide

Price Does Not Include:

  • Airline tickets
  • Personal expenses
  • Travel insurance
  • Entrance fees to archaeological sites to be paid on spot
  • Gratuities to your guides (if earned)

Day 1: Athens – Cape Sounion-Kythnos

Your day starts with a short stroll around the historic center of Athens, before you head to the marina and board the sailing boat that is going to be our home for the next week. Our skipper and guide will check you in your cabins and introduce you to the itinerary, after a short orientation. Late afternoon we leave the marina, enjoying views of the southern suburbs of Athens. We head east, towards one of the most iconic landmarks or both the ancient and the modern world. The Temple of Poseidon, built high on a cliff over the dark blue waters at Cape Sounion, is the place where the Aegean archipelagos gets its name from. Our destination for the night is the island of Kythnos. Gateway to the archipelago Kythnos boasts a lively main town, a world famous beach as well as postcard perfect views of the Aegean from the numerous chapels built high up in the cliffs. We’ll drop anchor in Kolona beach, a natural double bay separated by a strip of sand and spend the night there.

Overnight: Cabin aboard the sailing boat

Day 2: Kythnos – Serifos

Early in the morning, after breakfast and a swim, we hunt for fresh sea urchins in the cliffs on the southern side of Kolona beach. If you’re up for it, there’s a short, easy hike up to a white washed chappell, overlooking the Aegean. The centuries old structure’s courtyard is nowadays home to a small herd of wild goats and photo opportunities are abundant. Late morning we leave Kythnos behind us and sail south towards the island of Serifos. Well before the island’s marina, we stop for a swim in one of the various tiny bays that dot the island’s eastern side. Early evening we dock at the marina and head out to explore the island’s main town, up the mountain. With its tiny alleyways, numerous chappells and windmills, vibrant coffee culture and some insane views of the archipelago to the south Serifos is as iconic of Greece as anything. And if savoring deliciously fresh seafood right on the beach is your thing, this is the place to do so.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast

Day 3: Serifos – Milos

In the morning you have time for a quick swim, while we prepare the sailing boat for yet another amazing sailing experience. This time our destination is the cosmopolitan island of Milos, a volcanic island boasting unique geological formations. Some incredible sunset views without the crowds of Santorini is reason enough to visit Milos. Add in lunar like landscapes, a vibrant nightlife and incredible local food and you’ll get why the island is by far our favorite destination for our guests. If you’re a meat eater we’ll take you to THE place on the island to try lamb or goat stew and if you prefer seafood, the tiny fishing village of Apollonia is home to numerous family run tavernas serving fresh fish right on the water. In the evening we’ll take the local bus to the main town up in the cliffs. The town, with its traditional cycladic architecture is busy with travellers and locals alike, with boutique cafes, bistros, restaurants and shopping opportunities everywhere. If enjoying a cocktail on a balcony overlooking the Aegean is your thing, Milos delivers.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast

Day 4: Milos – Kleftiko bay

Milos is a volcanic island, which is evident by the bizarre geological formations one sees around the island. After breakfast we get a chance to sail to two stunningly beautiful swimming spots, starting with the Kleftiko beach, in the southern tip of the island. Kleftiko used to be a pirate’s cove and a visit there is one of highlights to any trip to the Cyclades. Crystal clear waters, sea caverns and rocks pointing towards the sky, all contribute to an amazing, unique landscape. We will use the dinghy (the sailboat’s inflatable motorboat) to cruise through the caves, and you can easily spend a half a day here, swimming and snorkeling. Hopefully we’ll get a chance to spot some mediterranean dolphins here. Music attracts them so bring your playlists. In the evening, we’ll head back to the marina in Milos and you’ll have the evening to yourselves to explore the island some more. Our guide and skipper will be there for you, to suggest things to do, places to visit and of course direct you to the most authentic of restaurants on the island.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast

Day 5: Milos – Polyaigos – Sifnos

After breakfast we leave Milos behind us head northeast passing by the straights of Kimolos. A short sail away is Polyaigos, a tiny, barren, uninhabited island that is home to a dwindling population of Mediterranean seals, usually hunting for fish near the sea caverns they call home. The highlight of any visit to Polyaigos island, besides marine wildlife lucky viewings, is swimming. The island’s south side boasts some of Europe’s most terrific beaches, ideal for swimming and snorkelling. You can also hike on the island, frequently coming across wild goats grazing by the sea. In the evening we set sail north towards the island of Sifnos. Our head skipper’s favorite place in the world is the bay of Vathy on the southern part of the island. We always try to spend a night there, as there’s a great sandy beach and two family run tavernas serving what is considered by many of our guests as their best meal in Greece. Think of fresh vegetables and salads straight from the garden, goat or beef stews, grilled lobster or mullets fresh from the sea and you get the idea.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast

Day 6: Sifnos – Kythnos

After breakfast it’s time to leave Sifnos behind us, as the island of Kythnos awaits once again. This time we head to the island’s eastern side, after a stop for a midday swim in a remote bay on the southern part of the island. Our destination of the day is the tiny fishing village of Loutra. Once there our suggestion is to unwind in the hot springs or opt for an insanely relaxing spa treatment. For 6 euros a session it’s a steal! Early evening our guide will take you on a guided tour of the island’s main town, which is a ten minute drive away. The main town is stunningly beautiful, full of traditional whitewashed ancient houses, cobblestone streets and alleyways, and boasts some of the best meat based food in the archipelago. Think of grandmas observing passersby from their tiny, well kept courtyards, delicious homemade baklava and chocolate pies, friendly locals and the ever present sense that time here truly slows down, and you get the idea. After dark feel free to enjoy a bottle of cold, locally brewed beer right on the water, or put on a bathing suit and observe the Milky Way, while relaxing in the natural pools where the hot springs meet the sea.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast

Day 7: Kythnos – Temple of Poseidon – Athens

After a cup of traditionally brewed coffee in the fishing village of Loutra, we leave Kythnos behind us and set sails towards the mainland and Cape Sounion, home to the temple of Poseidon. We drop anchor in one of the numerous bays close to the cliffs where the temple is built on and use the dinghy to get to shore. Once there, we’ll hike to the temple and have a guided tour of one of the most important archaeological sites this side of the world. Late afternoon we’ll head back towards the marina in Athens, stopping along the way for a swim. Once at the marina your guide will be there to accompany you to the center of Athens for a proper farewell dinner in the historical center of Greece’s capital.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast

Day 8: Athens

Early in the morning we pack our bags and bid farewell to the sailing boat that’s been our home for the past week and our adventure ends.

Meals Included: Breakfast

Payment and Refund Policies

If you have any questions or you’d like to book this trip, please contact us.

Custom itineraries available to this or any of the destinations we travel to.

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SPECIAL AIRFARES: Kutrubes Travel can assist you with your flight reservations to your destination with all major carriers. We offer special rates through our various airline contracts. Please call us or email us with your proposed travel plans and we will be sure to accommodate you and respond quickly.

Kutrubes Travel also offers a variety of other tours throughout this region. Contact us for detailed itineraries and descriptions.