Original
Sailing
Sail Greece: Mykonos to Santorini
4.9
Excellent
155 reviews
8 days
Start
Mykonos, Greece
Finish
Santorini, Greece
Trip Code
ZSRP
Min Age
15
Trip Size
1 - 11
Physical Rating
Transport
Boat
Accommodation
Overnight boat (7 nights)
From £1,469(8 days)
Trip Informations
Why you’ll love this trip
Hop between paradise islands in the iconic Cyclades by yacht – is there any better way? Swim in the Aegean Sea off the side of the boat and let the waves rock you to sleep each night.
Visit the chic waterfront bars that line the beaches of Mykonos, serving authentic Greek food and cocktails as the sun goes down. This is a great place to eat well and relax!
Explore the 11th-century monastery of Moni Hozoviotissis, wedged between the dramatic cliffs of Amorgos.
Watch the sunset from the coast or the deck every night and if you’re game, get up early for sunrise – where better to seize the day than on the sea?
Head away from the tourist trail to the remote Small Cyclades islands, chock-full of tavernas serving fresh seafood and small villages to explore.
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. Your friendly crew will be able to help with the effects of sea sickness if needed.
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 sun screen and a hat, and drink plenty of water to keep hydrated. See ‘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 night life.
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
Sail from Mykonos to Santorini on this Greek Island adventure
Move between the boat, the beach and inviting Greek villages on this relaxing eight-day sailing adventure between Mykonos and Santorini. Spend your days swimming in turquoise waters, lazing on white-sand beaches, sampling mouth-watering local cuisine and exploring coastal villages steeped in history, mythology and beauty. Visit the beautiful islands of Amorgos, Naxos, Small Cyclades and Ios, watch a host of spectacular sunsets and enjoy Greek hospitality before returning to the boat to be rocked gently to sleep at night.
Inclusions
Transport
Boat
Accommodation
Overnight boat (7 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:
The trip commences on day 1 in Mykonos at 4pm.
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 degrees Celsius, 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 'Joining Point Description' in the Essential Trip Information for details. 
TRIP KITTY:
This trip has a compulsory group kitty of EUR100 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. The kitty amount should be used as a guide. More than likely, you will not spend the full amount recommended however it's advisable to budget for this amount.
Reviews (148)
5 stars
138
4 stars
8
2 stars
2
Peigi
Oct 04, 2025
Highly recommend the trip to Greece! Jiorgos(George) was fantastic and informative, the boat was also good!
Lisa
Oct 04, 2025
Highly recommend Intrepid and sailing the Cyclades. Your experience, comfort, and respect for the environment is number one. We witnessed a few competitive brands that behaved in port badly and would not go elsewhere
Jaclyn
Sep 30, 2025
Touring the Greek Islands via sailing is a special experience . You will see the country in a different way and get to some of the smaller islands. Our skipper Foti was wonderful.
Claudia
Sep 30, 2025
We really enjoyed our trip and were in excellent hands with our skipper Fotis. Would widely recommend!!
Bashkim
Sep 20, 2025
Patricia
Sep 17, 2025
Sailing in the Aegean was so rewarding and more than met my expectations. Care and consideration underlined everything from the first emailed information to the final farewell. I am keen to return!
Nikolina
Sep 16, 2025
Morgan
Sep 16, 2025
This is the best way to get an amazing experience of Greek Island culture. Visiting busy and tranquil islands, ports, villages and major touristy hubs made this a trip diverse in experience. I’d do it again in a heartbeat! Already looking at the next intrepid adventure.
Miguel
Sep 10, 2025
The trip is well thought out, with enough time to get a snapshot of the islands. Nico the skipper did a brilliant job of managing the process and conveying passion for the sea, nature and sailing. The islands are fantastic for hikes/runs with elevation/views and open water swimming
Sydney
Aug 26, 2025
I loved this trip– it was truly a once in a lifetime experience to live on a boat for a week. I had time to recharge and relax while learning more about Greek culture and sailing. Our group had Fotis as our skipper, and he was both a lovely person as well as a highly knowledgeable and diligent guide. I spent my days swimming in the sea, enjoying quiet mornings on the boat, exploring the islands, spending time with new friends, eating delicious food, and going out to enjoy delicious drinks at night. This trip was exactly what I needed!
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