Original
Greece Sailing Adventure: Cyclades Islands
10 days • 4.9
5
Excellent
153 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 £1,351(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. 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.
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.
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.
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)
Optional activities
Syros - Dinner at local family home (min 5 customers required) - EUR25
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. 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.
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. 
SNORKELLING
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.
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 yourself or fellow travellers) The kitty will be collected when you arrive at the welcome meeting or in stages throughout your trip.
Reviews (152)
5 stars
139
4 stars
10
3 stars
2
2 stars
1
Meghan
Jun 13, 2025
This trip was amazing! I think this is the perfect way to see the Greek islands! It was fun, relaxing, and an absolutely beautiful! Space might be a bit tight with a full boat, but go in with a sense of adventure and an open mind! Our skipper Jorg was so amazing and made this a trip of a lifetime!
Lou
Jun 12, 2025
I loved being moored in the heart of the marinas as much as I loved exploring authentic and small Cycladic Islands. Skipper George made our trip. Thank you. It was all amazing.
Stephanie
Jun 11, 2025
What an amazing trip! Our Skipper Jorgos was nothing short of awesome! He had so much knowledge of all the islands and gave us so many good recommendations. Look forward to another trip in the future
Daniel
Jun 10, 2025
This trip was a dream come true. Sailing 9 islands in 10 days in the beautiful Cyclades was so memorable. The entire trip went so smoothly and far exceed any expectations we had. We had the best Skipper, Fotis. He made our trip such a wonderful experience through his passion for sailing and Greek culture. Fotis helped plan our schedule based on the wind which provided perfect sailing conditions and weather the entire trip. He has a real enthusiasm for Greek food and emphasized local products, something our group really embraced and made each island that much more unique. Fotis gave fantastic recommendations at each island for historical sites, restaurants, beaches and activities. This made each island easy to navigate and helped us have an authentic experience and make the most of our time in each location. He showed us how to make authentic Greek Salad which we loved and even made ourselves for him later in the trip! He took us to various swim spots including snorkeling spots that had a World War 2 German Hydro Plane. He went spear fishing, caught fish and brought it to a taverna for them to grill for us. We shared music from each of our countries and Fotis even showed us some Greek reggae which we loved. He was a very effective communicator. He ran the boat so well and smoothly and emphasized being a responsible tourist. He's also very funny! We couldn't have asked for a better Skipper, he truly made the trip special. I highly recommend this trip to anyone.
Gareth
Jun 05, 2025
Great trip. Learned a lot and the guides passion for all things sailing and Greek was infectious. I highly recommend and we valued the extra few days the 10 day version provided.
Kieron
May 22, 2025
This trip suits anyone who is active and enjoys others company.You work together to make the trip enjoyable to be taken to the most beautiful spots in the Greek Islands with a Captain at the helm with knowledge ,responsibility and caring.I highly recommend this trip
Nina
May 20, 2025
Really enjoyed, was well worth it
Amy
May 12, 2025
Jeff
Oct 21, 2024
An excellent way for sailors & non-sailors to experience the Greek Islands in a small group. Each island selected by Fotis had a unique offering. The experience was very well organised & even though I have done much sailing, I would not have enjoyed navigating the Greek Islands without the weather, port & island peculiarities knowledge Fotis had which made for a most enjoyable trip
Leah
Oct 20, 2024
Skipper Fotis was knowledgeable, passionate, and had a focus on safety. Due to winds our itinerary changed, only adding to the adventure. He gave excellent recommendations on food, things to do, with a desire for us to experience Greece as authentically as tourists can. Boat living isn’t for everyone but for the right people it is a hard trip to beat.
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