Original
Sailing
Sail Greece: Santorini to Mykonos
4.8
Excellent
143 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 £1,162(8 days)
Trip Informations
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.
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.
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 the Greek Islands between Santorini and Mykonos
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 (141)
5 stars
128
4 stars
8
3 stars
2
1 star
3
Lynda
Jul 18, 2026
What a fantastic and adventurous trip! Actually you need to make sure that you are able to be flexible for this trip. Stelios is a gold class skipper!!
Jess
Jul 18, 2026
Amy
Jul 18, 2026
Sailing around the Greek islands…absolute paradise! The best and unique way to experience the islands. We had a great trip and it was a good group! Age range from 21-65 from the UK and Aus. We ate out together lots of the nights but there was plenty of time for alone time if you preferred. Our skipper Stellios was fantastic, super skilled, amazing knowledge of the islands and really good fun. He came out with us to host some dinners and showed us the best beach spots too including a hidden cove. I would point out, if you book, be mindful that their may be variables with the trip Itinerary due to sailing conditions. This happened on our trip but it didn’t matter having to stay again in a beautiful harbour.
Minija
Jul 18, 2026
Absolutely loved it! Our skipper Stellios made the trip! If it wasn’t for him I think the trip would have been much less enjoyable. The only issue I had is the lack of advertisement that the itinerary is less of an itinerary and more of a very rough guide - we didn’t follow it at all due to winds which is something none of us had really considered due to lack of sailing experience (didn’t really understand the extent of how the winds impacted our movements). Definitely be prepared to go with the flow! Thanks again Stellios!
SALVATORE
Jul 14, 2026
It was a fantastic experience sailing and visiting Greece Islands
John
Jun 26, 2026
Sailing with Captain Nikos in the Greek Islands was enjoyable in many ways. Scenic Islands, excellent food, and everyone on board got along well. Not an intensive hands-on cruise like Mahina or Pangaea but still fun to sail thru the often brisk winds and waves that the Cyclades offers. You're in good hands with Nikos and Intrepid!
Sophie
Jun 25, 2026
Our Greece sailing trip was exceptional thanks to Nikos. His local knowledge, organization, and focus on safety made every stop seamless. We trusted his recommendations completely and experienced the authentic culture of each island. Intrepid was incredibly well-organized throughout. Tip: bring extra cash for smaller islands and local businesses.
Christopher
Jun 24, 2026
An excellent trip and an outstanding skipper / group leader. It is an authentic sailing experience, not a cruise ship. That is what makes it great. Sailing is dependent on weather and sea conditions. The skipper made sure we had an excellent experience given the winds and sea conditions. This trip has everything: sailing, history, snorkeling, culture, great food, and so much more. Another Intrepid trip of a lifetime.
Carolyn
Jun 21, 2026
An amazing holiday - I have wanted to do something like this for a long time and it didn’t disappoint. Lovely group, everyone got on very well. Ilias was brilliant - friendly, knowledgeable about the islands, and such an experienced sailor. We felt in very good hands. You have to be prepared for the itinerary to change a bit depending on the weather conditions, but Ilias explained everything well and we were all happy. The cabins are small, but it very clearly says that on the trip notes, and actually i was pleasantly surprised by the en suite bathroom! A fabulous 8 nights, and I’d definitely do it again!
Beth
Jun 20, 2026
Our tour of the Cyclades was a once in a lifetime trip. I can’t imagine a better guide than Nikolas for this sailing adventure. Each island had a unique feel and the Aegean Sea was beautiful.
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