Greece Sailing Adventure: Cyclades Islands

Sunsets, seafood and seaside views on this sailing trip in the Mediterranean

Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places.

Trip code: ZSRV

Start: Santorini, Greece

End: Santorini, Greece


Duration
10 days
Group size
1 to 11
Minimum age
15 years old
Style

Basix: Simple accommodation, local transport and lots of free time

Original: Tourist-class hotels, some meals included and a great mix of included activities and free time

Comfort: Comfortable accommodation, with a relaxed pace of travel and many included meals and activities

Premium: Our best accommodation, exclusive inclusions and our most experienced leaders

Original
Theme

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Sailing
Physical rating

Indicates how physically exerting a trip is, and how fit you will need to be to enjoy it. More info on physical ratings


From
EUR €1,845

Boats

Ocean Star 56 Boat
Ocean Star 56
PASSENGERS: 11
The Ocean Star 56  is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, the Ocean Star 56 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins, 2 twin cabins and 1 triple cabin,  the Ocean Star 56 is the perfect yacht for novices to learn the ‘ropes’.
Explore features

Why you'll love this trip

  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
  • Walk along the volcanic rim of Santorini, past white villages that cling to cliffs and watch as day turns to night during sunset at the caldera – this is a memory you’ll bring home!
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village.
  • Visit Mykonos for the quintessential Greek Islands experience. Embrace your hedonistic side with the boutique culture and nightlife or relax on one of the many beaches dotted along the coast.
This itinerary is valid for departures from 01 January 2026 to 31 December 2026.

View the itinerary for departures between 01 January 2025 - 31 December 2025

Itinerary

Map of Greece Sailing Adventure: Cyclades Islands including Greece

Inclusions and activities

Destinations
Greece
Transport

Boat

Accommodation

Overnight boat (9 nights)

This trip generates 15 kg of CO2-e per person per day

Learn more about our climate commitment.

When you travel with us, The Intrepid Foundation gives you more opportunities to support important causes in destinations you visit.

Before you book you should know

Dates and prices

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Important notes

START TIME
This trip starts on Day 1 in Santorini at 1pm

ACCOMMODATION ON BOARD THE YACHT
This trip is accommodated entirely on board a yacht of between 54ft to 56ft. The yacht can accommodate up to 11 traveller's in the following cabin types:
double bed cabins (x2)
twin bunk bed cabins (x2)
triple bunk bed cabin (x1)
There are 5 shared bathrooms. Our boats are real yachts, and this is a real sailing trip. Yachts are designed to keep sleeping areas to the absolute minimum of space, while maximising common areas as much as possible. Everyone including the skipper shares the bathrooms on board.
Solo customers can choose to book either a twin bunk bed cabin or a triple bunk bed cabin and will be matched up with other solo customers of the same gender. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge when booking either a twin or double cabin.
Rooms are allocated on arrival by our skipper according to group composition, which means it is not possible to reserve or guarantee any specific berth. If you are booking a bunk bed cabin you must be willing to sleep on the top bunk.
Double bed cabins can only be booked by 2 people travelling together or a solo customer who pays for a single supplement.
While not everyone may feel entirely comfortable living in such close quarters, those who are looking to revel in the adventure and exhilaration of an authentic sailing trip usually find any discomfort from cramped living conditions is more than made up for by the whole experience.

HOT WEATHER:
Summer temperatures can reach up to 40°C, 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.

PASSPORT DETAILS:
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.

ADDITIONAL ACCOMMODATION:
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 Essential Trip Information for details. 

TRIP KITTY:
On this trip it's compulsory to contribute to a kitty of EUR110 per person. The kitty is an on-ground payment put into a central fund managed by travellers. It helps fund for breakfast and lunch on the boat and other small items such as ice, water, snacks and drinks. Travellers are responsible for the preparation of these meals onboard and to shop at port where supermarkets are often very close to the mooring. Kitty amounts are subject to change to reflect local price increases. On day 1, the skipper will talk through the kitty and how it will be managed by the group. The kitty will be collected when you arrive at the welcome meeting or in stages throughout your trip.

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.

Reviews

4.9 . 183 reviews
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Jay
Traveled September 2025
Eugenie
Traveled September 2025
Timothy
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Elliot
Traveled August 2025
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Traveled August 2025
Greece Sailing Adventure: Cyclades Islands
From
EUR €1,845