Original
Sailing
Sail Greece: Santorini to Mykonos
4.9
Excellent
152 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 £1,093(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 (144)
5 stars
131
4 stars
9
3 stars
2
1 star
2
Elizabeth
Aug 05, 2026
This trip was the perfect combination of adventure and relaxation. We had plenty of time every day to explore a new island and eat at the local taverns. Our captain, Ilias, was very skilled and we had a great atmosphere on the boat. We loved swimming off the boat almost every day - the water was perfect.
Michael
Aug 05, 2026
Abigail
Aug 04, 2026
My 17 yr old son and I had the most fantastic trip, our Captain Ilias was superb, he is a brilliant sailor and we felt extremely safe. He also gave us lots of information about the islands and rerouted the trip so that we the best sailing experience. My son and I shared a bunk cabin which was brilliant, we had enough space, but yes the room was compact, but comfy and lots of fun. We swam at every island and had some great spots to swim on route. It was a really great trip, Greece is just stunning and to see the islands from a sail boat was the perfect holiday, highly recommend it
Murali
Aug 03, 2026
This trip was amazing! Ilias, the captain, was very friendly, knowledgeable, and professional. He taught my a little about each of the islands and was able to point me to things to see and do at each stop, as well as suggestions for places to eat, all of which were fantastic. The Greek islands are spectacular, and no words or photos can accurately capture their beauty. It was an amazing week, and truly a once-in-a-lifetime experience.
Bernard
Aug 03, 2026
Loukas was a fantastic captain—knowledgeable, approachable, and always helpful. When weather prevented sailing, he arranged great alternatives so we still enjoyed the trip. He made everyone feel welcome and greatly enhanced the experience.
Kay
Aug 02, 2026
Had an amazing holiday! We had a great group of fellow travellers, mix of ages and backgrounds. Ilias our skipper was very experienced, and although our itinerary was a bit different to the original one as a result of weather conditions, we still got to see a good mix of islands. Ilias always had recommendations for great places to eat, and things to see on the islands. Cabins are compact, so I was glad I followed the trip notes and packed light. Already planning my next sailing trip with Intrepid!
Cara
Aug 02, 2026
I highly, highly recommend this trip! I had a great adventure with a wonderful group of people and a super experienced and well organized captain. So worth it!
Will
Jul 22, 2026
This was truly the trip of a lifetime! Our skipper, Nikolas, was absolutely amazing. He even speared fresh fish for us to enjoy onboard and trolled for fish between the islands. We saw dolphins, jumping swordfish, and turtles, while every swim stop was breathtakingly beautiful. An unforgettable sailing adventure!
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!
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