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 £1,742(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 (197)
5 stars
186
4 stars
10
3 stars
1
Claudia
Aug 14, 2026
This trip was a trip of a lifetime and I will never forget it! A special mention to our skipper Dimitris, he was so attentive to every person on board and made sure we all had the best time and sailed smoothly. He also took us to swim spots that are only accessible by boat. His knowledge of the Greek islands was also amazing, including what to do at each island and the best local food options, I have never eaten Greek food this nice before. Thank you Dimitris!
Zara
Aug 13, 2026
I had a really great time on this trip. It was well organised and had a relaxed feel. We were well looked after by our skipper Dimitris, who did an excellent job. Highlights of the trip for me would be the friends I made, swimming spots we went to and dinners we shared.
Gavin
Aug 10, 2026
An unforgettable way to experience Greece. Exploring the Cyclades by boat gave us the chance to discover some incredible places while enjoying the freedom and adventure of life at sea. Fotis was a fantastic skipper and made the whole experience feel effortless and safe, plus his love of Greek food definitely rubbed off on us!
Kirra
Aug 09, 2026
I had the most amazing 10 days sailing around the Greek Islands with Intrepid! The whole trip was incredible, and having such an amazing skipper made it even more special. He was so funny, kind and made everyone feel completely at ease. Couldn’t recommend him highly enough! An unforgettable trip from start to finish.
Ange
Aug 09, 2026
Stelios was absolutely amazing !!!and made our trip truly unforgettable. He was incredibly knowledgeable, kind and attentive, and went above and beyond to make sure everyone felt comfortable and looked after. He taught us so much about sailing and the beautiful islands we visited, while making every day fun, relaxed and memorable. We couldn’t have asked for a better skipper — thank you, with all our hearts Stelio!🙏🏽⛵️🇬🇷💙
Kelly
Aug 09, 2026
This was the most amazing tour. Even with changes in the itinerary due to weather conditions, every alternative Island was amazing. Our skipper Stylios was absolutely the best and we felt so included in our sailing experience. I will recommend this trip to all!
Carol
Aug 09, 2026
Highly recommend for people who love adventure. It is a great way to see the islands. Our skipper was wonderful and every destination he picked was amazing.
Michelle
Aug 04, 2026
An incredible way to travel around the islands of Greece . Stelios was an accomplished sailor and l got to experience some memorable sailing. Stelios was always happy to help, he even rowed us to shore, cooked dinner and went out of his way to make arrangements to visit Naxos by ferry. I would do it all again.
Amy
Aug 02, 2026
A once-in-a-lifetime experience I’d recommend to anyone! Sailing was so exciting and a perfect opportunity to explore multiple different islands in the Cyclades, trying local cuisines and exploring different historical sites.
Robert
Jul 21, 2026
A great trip. Fotis our skipper was funny, intelligent, had excellent seamanship, and extensive knowledge of all the islands we visited. And swimming everyday in the clear waters of the Aegean was awesome! (Pack sensibly, storage space in your cabin is limited: luckily I didn't have to share my cabin.)
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