Hidden Cyclades Sailing Adventure
10 days from Saronic Gulf to Saronic Gulf
From $ 1505
Duration10 days

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.

This tour is operated by

  • Duration: 10 days
    Service level: Standard
  • Starts in: Saronic Gulf
    Physical Grading: Average
  • Ends in: Saronic Gulf
    Ages: 15+
Hidden Cyclades Sailing Adventure - Tour Map


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Day 1: Athens - Kythnos

Start place: Saronic Gulf

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. 
Day 2: Kythnos - Serifos
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.
Day 3: Serifos - Vathi
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.
Day 4: Kimolos
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?
Day 5: Polyaigos
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.
Day 6: Sifnos - Platys Gialos
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. 
Day 7: Serifos - Koutalas Bay
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?
Day 8: Kythnos - Agios Ioannis
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.
Day 9: Kea
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.
Day 10: Athens
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.

End place: Saronic Gulf



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    Overnight boat

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