Original
Sailing
Sail Greece: Mykonos to Santorini
4.9
Excellent
143 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 £1,508(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.
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 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)
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.
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 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. 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 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 (141)
5 stars
131
4 stars
8
2 stars
2
Elizabeth
Aug 11, 2025
Our trip was spectacular! From stunning swim spots only accessible by boat to exploring towns and beaches, our itinerary struck the perfect balance between smaller, quieter islands with fewer tourists and larger, more popular destinations. Our skipper Nikolas was amazing and provided us with fantastics recommendations at each stop. Truly the best way to experience Greece!
Patrick
Aug 10, 2025
Sailing in Greece was literally the best trip of my life. Couldn’t be happier with the whole experience. We couldn’t have asked for a better skipper. Nikos was extremely proficient in sailing and overall boat handling. He made a tough job look easy, which in turn made our experience relaxed but still exciting. Once in port, his knowledge of the local area at each destination enhanced our experience with great recommendations. Would 100% do it again if not for all the other trips Intrepid offers!
Emily
Aug 06, 2025
I could not recommend this higher, I wish I could keep it a secret but that would be a disservice. Our Captain Fotis was phenomenal and made the trip a dream. Everything could not have been more perfect from the boat, accomodation, local experiences, sailing experience, the swim stops, I could go on. Don't think twice!
laila
Aug 06, 2025
Travelled as a family with our 15yr old son. Fotis our skipper made this such a memorable trip for everyone (7 in the group), the perfect way to visit the islands in this area and a brilliant experience for our son to aid his travelling in future.
Arthur
Aug 05, 2025
Fotis , what a skipper he was such an amazing guy and we had such an amazing group. If you get him as your skipper you will definitely ‘ENJOY’ your trip. I will never forget Fotis , whenever i think of Greece Fotis will always come to mind. (Fotis 1.0 is the best)
Darrin
Jul 28, 2025
Our skipper, Jiorgos was excellent!!!! This is the main reason for a 10/10. Review. The trip details were clear about the details and what might be the contingencies, if required. The sailing boat was as described and in good condition and clean and the amenity was as expected. The group dynamics of 6 passengers and skipper was excellent. Any more passengers would have affected my rating for the trip, but not for Jiorgos. Trip of a lifetime!!! Ticked my "Bucket List" expectations very well. Just do it, you'll love it.
Bryce
Jul 27, 2025
What an amazing trip. I was blown away by how much I enjoyed being on a boat and what we saw. Our skipper jiorgos went above and beyond and such a beautiful human that made our trip truly unforgettable with a smile on his face alway. If you're thinking of booking. Just book it you won't be disappointed !!!
Perri
Jul 26, 2025
In short. Book this trip!!! My husband and I were apprehensive about a sail, due to our lack of experience sailing and about the prospect of sea sickness. But boy am I glad we booked it. We had the most phenomenal guide Jiorgos, who made our trip something we will remember for the rest of our lives. From sailing, dolphin watching and swimming in some of the most divine coves and secluded beaches, you cannot go wrong on this trip. We were fortunate enough to have been staying with another two lovely couples who also completed our trip. A full house may have been very overwhelming, but we were lucky enough to have only had 7 on board. If you’re wondering whether or not to book this trip, just do it! You won’t regret it. So many new experiences and such a great way to see Greece! It was a great mix of busy islands and some more relaxed and ‘less touristy’ options. 10/10 can’t fault a thing! Thank you Jiorgos and our new friends for an unforgettable week!
Hannah
Jul 22, 2025
This trip is incredible. If you love the sea, the sun, and a slower pace, this is the perfect trip. You will spend a lot of time on the boat and in the water which is the main theme, the islands are just a bonus! I loved the islands we visited, a real mix of quiet, calm and authenticity and some more lively islands like Naxos and Ios. The food, the people, everything is wonderful! Highly recommend
Stefanie
Jul 21, 2025
A one of a kind experience with excellent skippers. If you get a great group, you’re in for the best 8 days of your life!
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