Original
Greece Sailing Adventure: Cyclades Islands
4.9
Excellent
173 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 £1,737(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)
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. 
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 (171)
5 stars
161
4 stars
7
3 stars
2
2 stars
1
Timothy
Sep 13, 2025
Great trip - Fotis our skipper was passionate about sailing and the environment- he gave us detailed information about each island and the history. Oh and he’s got a great sense of humour which always helps !!
Katie
Sep 10, 2025
Nikolas is an excellent skipper, and any sailing trip with him will not only be safe, but fun and informative! This is definitely the best way to see the Cyclades - no hassle with carrying your luggage everywhere, and sailing the Aegean is so much fun! The trade off is the lack of space, but that’s easy enough to get over after a day or two. If you like swimming and exploring the Cycladic islands, you’ll love this trip!
Elliot
Sep 09, 2025
This trip was truly amazing. The captain was fantastic and explained everything. The sites we visited were unbelievable. I highly recommend this trip
Russell
Aug 25, 2025
We had a fabulous time on our Intrepid Greek Islands boat trip in the Cyclades, met fabulous group of people and our Captain Orestis Vellis was fantastic.
Colin
Aug 25, 2025
I couldn’t recommend this trip highly enough. The scenery was breathtaking, the boat comfortable, the size of the group just right. It was such a wonderful experience to be out sailing in the open sea, under the guidance of our very skillful skipper Fotis. Lots of time to look out and ponder the majesty of it all, time for good conversation. And time to explore the islands, their history, food and culture. I have returned home renewed, refreshed and recharged!
Lisa
Aug 24, 2025
I can highly recommend the 10 day sailing experience in Greece cruising through the islands. This is magical and I don’t think there would be any better way of experiencing this gorgeous part of the world
Ruchard
Aug 21, 2025
Caroline
Aug 20, 2025
The Cyclades sailing tour was life changing. I used to think my home country of New Zealand was the most beautiful country in the world but I have been proven wrong. Our tour was lead by the most capable, knowledgeable, and friendly skipper ever- George really turned our group of strangers into a bonded group of friends and I will never forget this trip as long as I live.
Emile
Aug 15, 2025
This might have been my favourite trip yet. Did not expect to be as blown away as I was (by day 2!) Our skipper, Fotis, was an absolute legend too. Intrepid, you've done it again.
patrick
Aug 14, 2025
Great introduction to sailing for those that have never sailed. Beautiful place to sail for those that have never sailed before or those that have. Greek food was very good. Greek coffee was even better. Now that was an unexpected surprise but I guess a surprise is unexpected. Best ice cream I have ever had. Best ice cream I have ever had. Indeed that needed to be said twice. Lovely swimming spots in beautifully clear azure blue and turquoise waters. Plenty of history and Gods for those interested which included me.
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