Original
Sail Greece: Santorini to Mykonos
4.8
Excellent
115 reviews
8 days
Start
Santorini, Greece
Finish
Mykonos, Greece
Trip Code
ZSRR
Min Age
15
Trip Size
1 - 11
Physical Rating
Transport
Boat
Accommodation
Overnight boat (7 nights)
From £1,304(8 days)
Trip Informations
Why you’ll love this trip
Spend your days island-hopping in the Cyclades, swimming in the clear waters of the Aegean Sea and sleeping aboard a private yacht.
See Santorini, where the blue and white villages cling to the rim of an ancient volcano – don't worry, the only fire you’ll see is in the island’s magnificent sunsets.
Break bread with locals in the sleepy fishing villages of the Small Cyclades islands, away from the typical tourist trail.
Taste rural life on the large island of Naxos – a great mix of historic neighbourhoods, gorgeous views and tasty Kitron liqueur.
Explore a place where Europe’s chic and beautiful come to play – consider staying a few extra days after your trip to soak up the beauty, charm and sunsets of Mykonos.
Is this trip right for you?
The majority of this trip takes place on a sailing boat and need to feel comfortable moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others – it's recommended that you bring sea sickness medication just in case.
Our yachts have a small Zodiac on board, 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 ‘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 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)
The majority of this trip takes place on a sailing boat and need to feel comfortable moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others – it's recommended that you bring sea sickness medication just in case.
Our yachts have a small Zodiac on board, 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 ‘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 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 the Greek Islands between Santorini and Mykonos
Dreaming of crystal-clear waters, whitewashed villages, historical ruins, lively Greek culture and deliciously fresh cuisine straight from the sea? Then sail from Santorini to Mykonos on this eight-day boat trip in Greece. Spend blissed-out days under sun drenched skies enjoying the best of the Greek Islands, including Santorini, Ios, Amorgos, the Small Cyclades, Naxos and Mykonos. Watch the sunset, explore olive groves, feast on fresh food and wine and fall asleep to the gentle rocking of your yacht every 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
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 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 Essential Trip Information for joining and finishing points.
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 (124)
5 stars
112
4 stars
8
3 stars
1
1 star
3
Tim
Sep 13, 2025
I just had the best vacation of my life on the boat with Jiorgos as skipper. Our group was also amazing and a perfect blend of personalities with strong positivity. Jiorgos gives you just enough information at each stop to go and investigate for yourself and have amazing surprises along the way. You can’t beat this! Bring a great attitude and you will have a great time on the boat.
Donna
Sep 10, 2025
This was a pinch me trip. Our captain Fotis was knowledgeable about each island. He provided us with tips and recommendations of where to eat, swim and what activities to do. We swam at the most beautiful locations. As a group we got on really well. We have made friends for life.
Hayley
Sep 10, 2025
The sail Greece was a once in a lifetime experience. Our skipper Fotis made our trip run so smoothly and he provided lots of insight about each island and always happy to help organise tours and experiences for the group. I highly recommend going on this trip, the islands were breath taking and the swimming spots felt like a dream.
Kevin
Sep 10, 2025
Intrepid is very organized. Nice mix of scheduled activities and time to yourself. Wonderful guides.
Hannah
Sep 03, 2025
Overall a great trip, and was a great way to destress and enjoy a beautiful location. Be aware there is a very real chance of itinerary changes due to weather, and that you may not sail every day or see every island. This was fine by me though, as there is plenty to enjoy and wherever you end up!
Abi
Aug 28, 2025
Lovely trip in a beautiful area of the world. Sailing the ‘wine dark sea’ is exciting and dramatic. Recommend.
Chloe
Aug 17, 2025
I highly recommend this trip, it was amazing. This is the best way to see the Greek Islands. Our guide Jiorgos was very knowledgeable and made the trip very special.
Nathan
Aug 17, 2025
Highly recommend to anyone who loves adventure, culture, and being part of a crew! The best holiday I've been on. Book it now
SASHA MARIE
Aug 17, 2025
We had an incredible journey sailing with our skipper Jiorgos. He was absolutely incredible!!!
Amy
Aug 17, 2025
My sister and I did the sailing trip around the Greek islands and we couldn’t recommend it more! Met the most amazing people and created such special memories on all of the islands we visited. Our guide Jiorgos couldn’t have been more helpful, taking us to the nicest restaurants, making us all feel safe and welcomed on the boat, and giving great recommendations on each island. Loved it! Would definitely recommend
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