Original
Sailing
Greece Sailing Adventure: Cyclades Islands
4.9
Excellent
202 reviews
10 days
Start
Santorini, Greece
Finish
Santorini, Greece
Trip Code
ZSRV
Min Age
15
Trip Size
1 - 11
Physical Rating
Transport
Boat
Accommodation
Overnight boat (9 nights)
From £1,514(10 days)
Trip Informations
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.
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.
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 – it's recommended that you bring sea sickness medication just in case.
Our yachts have a small Zodiac on board, which is used to transport travellers to shore if we need to anchor in the bay. However, we will most often overnight in the small marinas on each island we visit, so the Zodiacs aren’t used. Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and a can-do attitude are 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.
On your trip, the skipper will move the boat using the sails and motor; occasionally, they will need to use the motor for the whole trip. This choice is weather-dependent, so is unpredictable, but our expert skippers will keep you updated on any necessary itinerary changes. They love to sail and will raise the sails at every opportunity.
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.
If you’re travelling with your own group of friends or family and would like to book a private departure on this sailing trip, our Tailor-Made team will be happy to help: https://www.tuuur.com/tailor-made https://www.tuuur.com/tailor-made (https://www.tuuur.com/tailor-made)
Itinerary
Sunsets, seafood and seaside views on this sailing trip in the Mediterranean
Inclusions
Transport
Boat
Accommodation
Overnight boat (9 nights)
Dates and availability
Starting
Ending
Remaining
Prices From
















Important notes
Reviews (195)
5 stars
185
4 stars
8
3 stars
2
Amanda
Jul 18, 2026
Trip was fantastic. You need to adaptable to itinerary changes but the other places are not a disappointment. Yacht and skipper were fantastic. So much sea swimming, relaxing and off the beat places visited!
Rachael
Jul 11, 2026
A wonderful adventure and experience. Our skipper was great and set sail to beautiful breathtaking locations that were each unique. Great memories created.
Rick
Jul 11, 2026
We sailed through some of the Cyclade Islands. We enjoyed swimming, exploring, shopping, and dining. We made some new friends on the journey. All of this was made possible by our calm and collected Captain Dimitri. I know he always engages new groups but he made our experience feel fresh and new.
Lisa
Jul 11, 2026
Our Intrepid trip around the Cyclades, met all expectations, with regards to itinerary, sailing, people, food. I travelled with my two young adult daughters in a triple cabin and it was perfect, a memorable experience 😍
Jessica
Jul 11, 2026
Our second yacht trip with Intrepid. Always excellent skippers and like minded travellers. So much fun in stunning surroundings. An incredible way to explore the islands minus the crowds!
Anna
Jul 09, 2026
Our boat trip was awesome: our skipper Fotis made sure we felt home and welcomed on board, and gifted us with his amazing sailing skills and deep knowledge of Greek culture, habits and life. We followed the wind and we were very lucky, as we also managed to visit smaller islands, wilder and so authentic. As a huge lover of Greece, this trip was just fantastic. Unsolicited tip: sailing depends on the wind, just follow it and try to forget the programme — to me, it’s the best way to make the most of the trip! Bravo, Fotis!
Michelle
Jul 04, 2026
This trip was amazing. Our skipper was sensational and took us to more islands than we expected. It was fun too with plenty of swimming opportunities. Loved it
Kim
Jun 30, 2026
Just came back from a 10 day Greek island sailing trip with the most Jorgios, the most amazing skipper possible! We visited a different island every day, Jorgios really set the benchmark high, with his extensive knowledge, professionalism, personality, and extensive information which he gave us when we arrived at every island.. had such a great time,, I’m doing another one in two weeks.. very happy with Intrepid and our skipper I will continue every year doing another sailing trip with Intrepid
Nick
Jun 30, 2026
The Cyclades sailing trip was the trip of a lifetime. The skipper Jiorgos was friendly, engaging, highly competent and connected us with local knowledge. Swimming off the back of the boat and snorkelling were highlights. I highly recommend this trip and Jiorgos the skipper
Carrie
Jun 22, 2026
Sailing the Cyclades was the most incredible adventure I’ve ever experienced! It was an amazing way to see so many places and explore Greece in a much more intimate and informed way. I will never forget this trip and would highly recommend it to anyone.
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