Original
Sailing
Sail Greece: Mykonos to Santorini
4.8
Excellent
168 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 £1,189(8 days)
Trip Informations
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.
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
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
Reviews (162)
5 stars
148
4 stars
8
3 stars
2
2 stars
3
1 star
1
Michael
Jul 16, 2026
We had a fantastic time on our Intrepid sailing trip. Ilias was an excellent captain—professional, friendly, and always helpful. We felt safe throughout the journey and appreciated his calm, confident leadership. He made the experience enjoyable and memorable. Highly recommend!
Leanne
Jul 11, 2026
If you are looking for some fun in the sun & the water this is the trip for you. Bring your enthusiasm, water shoes for the beach (game changer) & remember that while the rooms maybe small you'll be spending more time in the water & up top
Myles Jeffrey
Jul 11, 2026
An unforgettable adventure! Stunning islands, a fantastic group, and an exceptional captain who made us feel safe every day. The itinerary was perfectly organized, and every destination was breathtaking. I would recommend this trip to anyone wanting to experience the best of the Greek Islands by sail! ⭐⭐⭐⭐⭐
Sophie
Jun 29, 2026
I had the most amazing week sailing in Greece. Our skipper Nikos was awesome and made sure we all had a really great time. We got to see some really cool islands that were smaller and not just tourist traps. Overall an incredible experience!
James
Jun 29, 2026
Nikolas has great local knowledge and was an amazing skipper
Jonathan
Jun 28, 2026
A great trip hopping around the islands by sail boat, Nikolas our leader was amazing, he always made sure we had a good time and kept us safe.
Ralph
Jun 17, 2026
I strongly recommend the small sailing boat cruise through the Cyclades with Captain Nikolas and Intrepid. He was a master sailor, always navigating under sail whenever possible. He was great about teaching sailing technique and allowing guests who wished to help the ability to do so. He also knows all the best swim sites. restaurants, (and gelato places!) Super nice guy. And we made good friends with some interesting travelers from around the world. Would highly recommend!!!
Doni
Jun 13, 2026
Thoroughly enjoyed my Intrepid sailing trip through the Greek Cyclades and every day exceeded my expectations. I’ve been to some pretty amazing places and thanks to Intrepid and Captain Nikolas, Greek Cyclades ranks as one of the best, most memorable trips I’ve taken. The food, culture, sites people, and all hospitalities of Intrepid were first class
Richard
Jun 13, 2026
The sailing trip from Mykonos to Santorini was an amazing experience. I have done lots of travel, including adventure travel, but I can honestly say this was up there with the best travel experiences I have had. The azure, nearly indigo waters of the Aegean Sea, golden sandy beaches, burnt dry hills, and interesting architecture and incredible food all made the trip an unforgettable experience. Our guide, Nikolas, was informative, humorous, and an extremely good sailor, which all made for a very enjoyable trip. I will definitely be back for another Intrepid trip as soon as the opportunity arises.
Michaela
Jun 10, 2026
I greatly enjoyed my trip from Mykonos to Santorini! The islands we visited were stunning with a perfect mix of busy towns and quiet beaches. There were lots of swimming opportunities when I went in June. The skipper, Ilias, was fantastic - he gave us thorough recommendations of things to do on the islands and was always willing to answer the many questions we had about sailing and life in Greece!
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