Original
Sailing
Greece Sailing Adventure: Cyclades Islands
4.9
Excellent
196 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 £1,919(10 days)
Trip Informations
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
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.
Inclusions
Transport
Boat
Accommodation
Overnight boat (9 nights)
Dates and availability
Starting
Ending
Remaining
Prices From
















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.
Reviews (187)
5 stars
175
4 stars
9
3 stars
2
2 stars
1
Mike
Oct 24, 2025
I would fully recommend this trip our Captain was excellent and made us feel.special trip of a lifetime
Pieter
Oct 24, 2025
Lovey trip, even if the weather at the end of October was unexpected. Our skipper did a great job navigating around it to make sure we still had a fantastic adventure.
Stacey
Oct 24, 2025
We really enjoyed our Sailing Trip with Jorg, he is an excellent skipper! We had some rough weather but always felt safe. He knew all of the best swim spots! Highly recommend but look out for those sardines jumping through the cabin window 🤣 thanks Jorg and Intrepid.
Tim
Oct 09, 2025
Wow what a trip. George was our skipper and he is a brilliant yachtsman and a great leader with the best sense of humour. He guided us round the Cyclades like a master. Made some great friends as well. Just do this trip and you won’t regret it
Yasmin
Oct 06, 2025
I had the experience of a lifetime. I booked this trip knowing it was something out of my comfort zone and loved it. I feel it was an accomplishment for me.
Michael
Oct 06, 2025
It was a great way to see a number of Greek islands and the small towns from a local's perspective. It was also a very comfortable way to travel between the islands versus the ferries. The sailing was everything from motoring to very fast sailing in a good wind. The skipper (Fotis) was very knowledge and competent. Fotis was delightful. He had lots of information to share about all of the areas that we sailed in and Greece in general, including the history, culture and food. He was clear in all communications, very agreeable and fun to spend time with. We had a very enjoyable trip in no small part because of Fotis.
Khoa
Oct 03, 2025
Fotis was a fantastic skipper and provided us with great insights into the history and culture of Greece while providing local favourites among each island. The food, sight seeing and swimming locations recommended by Fotis were always great and provided an authentic Greek experience.
Fiona
Oct 03, 2025
I cannot recommend this trip enough. I genuinely cannot remember feeling this happy and content with the world for a very long time. It has been immensely good for the soul. Treat yourself and book up asap.
Tracy
Oct 01, 2025
Nikos you were an absolute champion of a skipper for our Cyclades sailing trip and we enjoyed every minute . The drone photos were a bonus for all the beautiful swimming stops. Would recommend this trip in a heartbeat.
Cheryl
Sep 29, 2025
Just got back from an unforgettable sailing trip through the Aegean Sea with Intrepid — and it was incredible! Our skipper, Fotis, was fantastic: experienced, friendly, and full of local knowledge. We visited beautiful islands, swam in crystal-clear waters, and enjoyed quiet coves and authentic seaside villages. The boat was comfortable, and the whole trip was the perfect mix of adventure and relaxation. If you're looking for a unique way to explore Greece, I highly recommend this trip!
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