After the ultimate in relaxation? Look no further than a sailing trip through the Hidden Cyclades.

Sail through the Cyclades exploring the hidden islands so often overlooked by tourists. Forget paradise lost, it's waiting to be found on small islands like Serifos, Sifnos, Kythnos and Milos, where the blue and white buildings lean more towards authentic than aesthetic. Explore the white, lunar-like landscape of the Moon Beach, Sarakiniko, and dine on fresh seafood in the small, local tavernas, washed down with a glass of ouzo. Whether it's by boat, swimming or snorkelling, the Aegean is waiting to wrap you in its warm, salty embrace, as are the hardy locals who call these islands home.

Athens, Greece
Athens, Greece
Physical rating
Min 15
Group size
Min 1, Max 11

Why you'll love this trip

  • The Aegean is one of the best places in the world to explore by boat, with small villages, deserted beaches, incredible food and crystal-clear, unbelievably blue water.

  • Spend your days hopping between the small islands of the Cyclades.

  • Visit the ruins of Karthaia and see temples dedicated to Athena and Apollo, as well as the ancient theatre, just up the hill from a beautiful beach.

  • With a maximum of eleven people on this trip, you'll be able to cram into the traditional tavernas lining the ports for an authentic culinary experience.

Is this trip right for you?

  • As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. Your friendly crew will be able to help with the effects of sea sickness if needed.

  • A zodiac is used to transport passengers from the boat to the mainland, with landings taking place at piers (dry landings) as well as on beaches (wet landings). Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and can-do attitude is all you need.

  • This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.

  • Time on the water also means time in the sun. Remember to pack sun protection, such as sun screen and a hat, and drink plenty of water to keep hydrated. See the 'Packing' section of the Essential Trip Information below for a full packing list.

  • Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if the weather becomes unfavourable. If any changes are made, you can trust in your knowledgeable skipper to choose an alternative route or activity.

  • Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travellers. If you’re planning to have a late night, it’s a good idea to head into town and experience the local night life.


Welcome to Greece! Meet your group at 11 am on Athens' southern coastline and board your boat for a safety briefing before sailing out towards Kythnos, an island in the Western Cyclades. Feel the spray of salt and the wind in your hair during a six-hour sail while getting to know your group, and spend the evening anchored offshore, waking up the following morning next to a beautiful beach. 
Meals Included
There are no meals included on this day.
Enjoy a relaxed morning swimming or exploring Kythnos' gorgeous beaches. Eat lunch on board before heaving up anchor sailing towards Serifos, stopping in Livadi Bay. Serifos was a place of exile during Roman times but the only exile these days is willingly self-imposed. With small blue and white houses built into the hill, countless beaches and a strong presence in Greek mythology, Serifos is a destination that'll lodge itself deep in your heart. Or maybe it won't, but it's still a phenomenal place to spend an evening. Anchor in the bay and take a dinghy to shore to eat at one of the traditional tavernas at Livadi's harbour and enjoy the sunset, then pick up supplies and an ice-cream before returning to the boat.
Meals Included
There are no meals included on this day.
Take an optional morning walk (approx. one hour) to the hora (town) of Serifos, for beautiful views of the island and the Aegean Sea. Enjoy a coffee in the town square before making your way back down the Livadi's harbour and taking the dinghy back to the boat where you'll have lunch. After lunch, sail the town of Vathi, on Sifnos, and arrive in time for an early evening swim. Don't worry, it doesn't matter what time you swim in these waters, it's always warm. Take a dinghy to shore and eat at a beautiful, beachfront taverna, perhaps with raising a glass of ouzo with the group, then spend another night anchored offshore in the bay.
Meals Included
There are no meals included on this day.
Spend the day sailing south to Kimolos and swimming in the ridiculously clear water until evening. Kick back on deck with a good book, or a bad one, and get to know the people in your group with some quality bonding time soaking up the sun. Fun fact: Kimolos may be small, but approximately eighty churches have been built by the townsfolk and once you visit the island, you'll find yourself worshipping its very existence. Visit the main village for dinner and enjoy fresh seafood and, of course, some more ice cream because you are on holiday, right?
Meals Included
There are no meals included on this day.
Set sail from Kimolos to Polyaigos with a swim stop on the way. Lots of options including Sarakiniko, known as Moon Beach thanks to its lunar-like landscape. The dazzling white rock formations are twisted into incredible shapes as a result of erosion from the wind and sun, juxtaposed with the deep turquoise waters of the sea. This is THE spot to get that holiday happy snap and make your friends back home unbelievably jealous. If time and weather allows and you’re up for a longer sail, we can sail the south side of the island and to Kleftiko, a crazy-beautiful cove accessible only by boat. Revel in the rock formations and caves that are purported to hide pirate treasure, then sail to Polyaigos where you'll spend the evening. Polyaigos is an uninhabited island, unless you count the goats on land and the rare Mediterranean monk seals that call the sea caves home. Tonight, you'll be protected by Polyaigos' cliffs with dinner prepared by the group, so enjoy an evening together under the stars.
Meals Included
There are no meals included on this day.
Sail to the Platis Gialos Marina on the southern end of Sifnos and spend the day relaxing and swimming at its sandy beach. Here, you'll have lunch (maybe a cold Mythos beer too) and pick up supplies for the rest of the journey. In the evening, take a bus up to the village of Artemonas then enjoy a short stroll to Apollonia, where the group will have dinner. There's also an option to take a short taxi to Kastro, the ancient capital of the island. Apollonia is the modern capital of Sifnos and the centre of the island's nightlife, which resembles an earlier version of Mykonos – think unpretentious bars and restaurants found in paved, winding alleyways. Return later in the evening to the marina and overnight on the boat. 
Meals Included
There are no meals included on this day.
Prepare for a super relaxed day. Sail to Koutalas Bay or north to the far side of Serifos to Psili Ammos, which was voted Europe's Best Beach in 2003 by the Sunday Times. It translates as 'soft fine sand', and nothing much has really changed in the past 15 or so years – it's still a stellar stretch of sand. Wherever the boats end up, you'll enjoy swimming and taking dinghy rides to explore the coastline. The boat will remain anchored in the evening and the group will prepare dinner as the sun sets. It's not a hard life, is it?
Meals Included
There are no meals included on this day.
Today you'll return to the island of Kythnos, north of Serifos. But before you arrive, there's a swim stop at Agios Ioannis Beach. A quieter beach than its neighbour Psili Ammos, it's the perfect place for a mid-morning swim, a visit to the small church of Agios Ioannis or to find a quiet place on the beach to practice a few yoga moves. Continue sailing to Loutra, a small port at the northern end of Kythnos where you can explore the unexpected hot spring, grab dinner and some drinks in a local taverna.
Meals Included
There are no meals included on this day.
Wake up to another day in paradise, this time sailing north to the island of Kea. Hit the beach at Mikres Poles on Kea's southside and check out the ancient Karthaia ruins. Karthaia was one of the four ancient cities of Kea, and these days you can see the remnants of two temples, dedicated to Athena and Apollo, as well as the theatre. Continue up to Vourkari, a small village with a buzzing atmosphere thanks to its proximity to Athens and popularity with travellers, both Greek and foreign. Enjoy a farewell dinner at a beautiful taverna in town and, if you haven't already, raise a glass of ouzo to your new nautical friends.
Meals Included
There are no meals included on this day.
Depart early from Kea on your final morning, at around 7 am. Sail back to your starting point, a marina on Athen's southern coastline, approximately six hours from Kea. Arrive and disembark the boat around 1 pm, at which point this sailing adventure comes to an end.
Meals Included
There are no meals included on this day.
Special Information
If you are flying out of Athens today, please do not book flights to depart prior to 4pm.


No meals are included on this tour




overnight boat (9 nights)

Dates & availability

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Important notes

This trip commences at 11 am at Alimos Marina, which is a suburb of Athens. The boat will set sail shortly after so all travellers should be at the marina promptly at 11 am. If you are delayed we can assit you with making arrangements to our first stop Kythnos but this will be at your own expense.

Summer temperatures can reach up to 40 degrees Celsius, which can be uncomfortable for those not used to the heat. Please consider the time of the year you wish to travel and your suitability to that season.

The minimum age on this trip is 15. 

Please provide full passport details at time of booking including exact name as per passport, date of birth, nationality, issue and expiry dates as these are essential for booking services on this trip.

Dietary requirements are required at the time of booking so that any included meals can be properly catered for.

Please note that the majority of our sailing trips start and/or finish at a marina or port. If you have pre-booked any additional accommodation through us, you will need to make your own way to the joining point on Day 1 and from the finish point on the final day.
We do not provide transfers between hotels and the port/marina. Please check the 'Joining point instructions' and 'Finishing point' section in the Essential Trip Information for details.

Essential trip information

Want an in-depth insight into this trip? Essential Trip Information provides a detailed itinerary, visa info, how to get to your hotel, what's included - pretty much everything you need to know about this adventure and more.

View Essential Trip Information