Hidden Cyclades Sailing Adventure

10 Day Sailing Adventure from Athens to Athens with Intrepid

Book online and enjoy exclusive savings on Intrepid's 10 Day Hidden Cyclades Sailing Adventure. 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...read more

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$ 1,505
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$ 1,023
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Sailing Yacht
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Scenic / Cultural
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1 Athens - Kythnos
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.
2 Kythnos - Serifos
Enjoy a relaxed morning swimming, stand-up paddleboarding and exploring Kythnos' gorgeous beach. 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.
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.
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?
5 Polyaigos
Spend a day sailing around Milos and exploring its coastline. Milos is one of the bigger islands in the area and your first stop is 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 turquois waters of the sea. This is THE spot to get that holiday happy snap and make your friends back home unbelievably jealous. Continue sailing around the island 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 unihabited 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.
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.
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, mucking around on stand-up paddleboards 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?
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 and time for you to really work on those stand-up paddleboard skills. Maybe combine it with a bit of yoga practice and flip into a nautical headstand, because hey, the worst case scenario is falling into the warm embrace of the glittering water. Continue sailing to Loutra, a small port at the northern end of Kythnos where you can grab dinner and some drinks in a local taverna.
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.
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.

Intrepid Inclusions

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Sightseeing Highlights
  • 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 eight people on this trip, you'll be able to cram into the traditional tavernas lining the ports for an authentic culinary experience.
  • Overnight boat
Included Meals
    No meals are included on this tour
Read Trip Notes
  • Trip Notes outline what's included, visa information, important notes, how to get to your accommodation, packing checklist, optional activities, travel insurance requirements - pretty much everything you need to know about this adventure and more. Please take time to have a read through, and contact us if you have any questions. View Trip Notes

Prices & Dates

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Trip Starts Trip Ends Status Offer Save Now Our Price  
Saturday 20 Jul 2019 Monday 29 Jul 2019 1,014per person 1,568per person Enquire
Tuesday 30 Jul 2019 Thursday 08 Aug 2019 1,015per person 1,614per person Enquire
Friday 09 Aug 2019 Sunday 18 Aug 2019 1,015per person 1,614per person Enquire
Monday 19 Aug 2019 Wednesday 28 Aug 2019 976per person 1,558per person Enquire
Thursday 29 Aug 2019 Saturday 07 Sep 2019 1,023per person 1,626per person Sold Out
Sunday 08 Sep 2019 Tuesday 17 Sep 2019 939per person 1,505per person Enquire
Wednesday 18 Sep 2019 Friday 27 Sep 2019 939per person 1,505per person Enquire
Saturday 28 Sep 2019 Monday 07 Oct 2019 939per person 1,505per person Enquire
Saturday 09 May 2020 Monday 18 May 2020 51per person 2,518per person Enquire
Tuesday 19 May 2020 Thursday 28 May 2020 51per person 2,518per person Enquire
Friday 29 May 2020 Sunday 07 Jun 2020 51per person 2,518per person Enquire
Monday 08 Jun 2020 Wednesday 17 Jun 2020 51per person 2,518per person Enquire
Thursday 18 Jun 2020 Saturday 27 Jun 2020 53per person 2,611per person Enquire
Sunday 28 Jun 2020 Tuesday 07 Jul 2020 53per person 2,611per person Enquire
Wednesday 08 Jul 2020 Friday 17 Jul 2020 55per person 2,704per person Enquire
Saturday 18 Jul 2020 Monday 27 Jul 2020 55per person 2,704per person Enquire
Tuesday 28 Jul 2020 Thursday 06 Aug 2020 55per person 2,704per person Enquire
Friday 07 Aug 2020 Sunday 16 Aug 2020 55per person 2,704per person Enquire
Monday 17 Aug 2020 Wednesday 26 Aug 2020 53per person 2,611per person Enquire
Thursday 27 Aug 2020 Saturday 05 Sep 2020 53per person 2,611per person Enquire
Sunday 06 Sep 2020 Tuesday 15 Sep 2020 51per person 2,518per person Enquire
Wednesday 16 Sep 2020 Friday 25 Sep 2020 51per person 2,518per person Enquire
Saturday 26 Sep 2020 Monday 05 Oct 2020 51per person 2,518per person Enquire
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Note: Your Global Journeys Travel Advisor will check the availability of your departure date when you enquire. Additional savings may apply. We guarantee the lowest price in Australia. T&C’s apply.

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Trip Notes
Trip prices are per person, and reflect applicable discounts. Discounts are subject to availability, exclusive to Global Journeys and may be withdrawn at any time without notice. Trip prices are correct at the time of the products going live, however are subject to confirmation at the time of booking. All trip information is correct at time of trips going live, however are subject to change by Intrepid. Full terms & conditions are available here.