Greece Sailing Adventure: Cyclades Islands

10 Days | Sunsets, seafood and seaside splendour in the Mediterranean

4.9 out of 5 based on 88 reviews submitted.
EUR €2,050
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Fulfil your dreams of sailing the Greek Islands on a ten-day seafaring adventure around the renowned Cyclades. Setting off from Santorini, 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 the Aegean’s turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places. Trust us – it’s all smooth sailing from here.

Trip overview

Map of Greece Sailing Adventure: Cyclades Islands including Greece
Santorini, Greece
Santorini, Greece
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
Min 15
Group size
Min 1 - Max 11
Trip code
This trip generates 16.3 kg of CO2-e per person per day.
We offset these emissions on your behalf. But we know that is not enough, so we also have a carbon reduction target.

Why you'll love this trip
  • A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
  • 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.
  • 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. This is island living, Greek style.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
  • No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

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. Most of our departures run in peak season, when the seas are calmer. The ship will experience some roll and pitch in choppy conditions, however all of our ships come equipped with stabilisers to minimise movement. There will be seasickness tablets on board and your crew will do all they can to minimise any discomfort.
  • 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 sunscreen and a hat, and drink plenty of water to keep hydrated. See 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 nightlife.


Ocean Star 56 Boat
Ocean Star 56
On this itinerary, you'll be travelling aboard the Ocean Star 56
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Map of Greece Sailing Adventure: Cyclades Islands including Greece





Overnight boat (9 nights)

Dates and availability

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Important notes

This trip starts on Day 1 in Santorini at 1pm

This trip is accommodated entirely on board a yacht of between 54ft to 56ft. A typical yacht for 11 travellers is equipped with a mixture of 2 x double cabins, 2 x twin cabins and 1 x triple cabin. 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.

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 or cabin. Single passengers will be paired up with another passenger of the same gender, this may mean sharing a double cabin with a double mattress. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge. Everyone including the skipper shares the bathrooms on board.

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.

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.

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 Essential Trip Information for details. 

There are many opportunities for snorkelling during this trip. Diving masks, snorkels and fins are provided onboard the yacht and are for use by all passengers. They are disinfected prior to use. Some customers may prefer to bring their own diving mask and snorkel from home and just use the fins available on board.

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.

Read Essential Trip Information


4.9 out of 5 based on 88 reviews submitted.
While we try our best to display all reviews, removal may be due to the following: privacy concerns, profanity/inappropriate content or it is unrelated to this trip. We welcome honest feedback and will directly respond to negative reviews.

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Julie · Traveled August 2023
Sailing the Greek Isles far exceeded my expectations. All of the places visited were stunning and it was a great way to tick off some of the smaller Greek Islands. George and Oreistis were amazing hosts and looked after the group very well.
Review submitted 03 Sep 2023

Paul · Traveled August 2023
A fantastic trip sailing around some of the many Greek islands, most days included a swim stop in the pristine waters, the skipper offers information at each stopover to further enhance the island experience.
Review submitted 04 Sep 2023

David · Traveled August 2023
I’m amazed by how wonderful this trip has been. The captain, the guests, the Cyclades isles themselves made this sailing trip wonderful and unforgettable!
Review submitted 24 Aug 2023

Pahnia · Traveled August 2023
My partner and I went on this trip together and had a wonderful time! The boat was lovely, we really enjoyed sailing time (it was very relaxing haha) and all of the beautiful swimming spots we got to stop at. Make sure you listen to the pre-warning that the itinerary is just a guide and your destinations are dependent on the wind & the availability of the marinas - just go with the flow and you’ll have a great time! Our skipper was Fotis and he did an all round fantastic job - but a particular highlight for us was that our group asked him to organise family style dinners for us almost every night (I think all but two nights), where Fotis chose the restaurant and ordered a selection of traditional Greek dishes for us all to share. It really added to our experience and got us to try things we normally wouldn’t have chosen ourselves. We really appreciated the extra effort he put in for us - thank you Fotis!
Review submitted 24 Aug 2023

Jennifer · Traveled August 2023
Let me say, I love Intrepid trips. This one just feel short of expectations. There are so many factors that will define your experience on the boat. Unfortunately, I had many adverse factors. 1) It was very hot. The cabins were too small to cool off and sleeping was near impossible. 2) The trip was full and the boat was not comfortable for sailing in the morning. Not all 11 people could sit outside in a shaded spot. Those in the shade had to sit shoulder to should with others on an uncomfortable bench. 3) Our group was ok. Our captain had a bit of a short fuse. He did, however, have stuff going on in his life and he left a few days into the trip. That may have been affecting him. You do not have much control over certain factors. However, this is one thing you need to be aware of. This trip was offered as a beach and cocktail party trip. This is not why I travel. Intrepid is usually awesome at giving people a cultural and historical experience. The captains (I had two) seemed baffled when I asked about going to archaeological sites on the islands. Our second captain did everything he could to meet our needs in this area but I feel our first captain didn't even know where to start. Usually, with Intrepid, the guide provides many options for touring the location. The guide usually arranges taxis or local guides. This did now happen on this trip nor did the guides seem prepared for such requests. Intrepid needs to provide the guides on these boat tours with more knowledge and resources. So, if this trip sounds good, especially if you want beaches and cocktails, go for it. If you want more of a cultural experience be prepared to do your research and arrangements. Just know what you are getting into.
Review submitted 16 Aug 2023
Greece Sailing Adventure: Cyclades Islands
EUR €2,050