Original
Sailing
Sail Greece: Mykonos to Santorini
4.8
Excellent
circle168 reviews
location_on 8 days
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Start
Mykonos, Greece
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Finish
Santorini, Greece
tour
Trip Code
ZSRP
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Min Age
15
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Trip Size
1 - 11
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Physical Rating
airport_shuttle
Transport
Boat
bed
Accommodation
Overnight boat (7 nights)
From £1,205(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
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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.
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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!
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Explore the 11th-century monastery of Moni Hozoviotissis, wedged between the dramatic cliffs of Amorgos.
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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?
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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?
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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.
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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.
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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.
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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.
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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.
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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.
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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
- DAY 1Day 1 • Mykonos
- DAY 2Day 2 • Syros
- DAY 3Day 3 • Naxos
- DAY 4Day 4-5 • Small Cyclades
- DAY 5Day 6 • Amorgos
- DAY 6Day 7 • Ios
- DAY 7Day 8 • Santorini
Inclusions
airport_shuttle Transport
Boat
bed Accommodation
Overnight boat (7 nights)
museum Optional activities
circleSyros - Dinner at local family home (min 5 customers required) - EUR25
Dates and availability
Starting
Ending
Remaining
Prices From
Tuesday Aug 11, 2026
Tuesday Aug 18, 2026
Trip size max: 11 - Sold Out
Saturday Aug 15, 2026
Saturday Aug 22, 2026
Trip size max: 11 - Sold Out
Tuesday Aug 25, 2026
Tuesday Sep 01, 2026
Trip size max: 11 - 2 spaces left
£1,581
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Saturday Aug 29, 2026
Saturday Sep 05, 2026
Trip size max: 11 - 5 spaces left
£1,482£1,205
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Tuesday Sep 08, 2026
Tuesday Sep 15, 2026
Trip size max: 11 - 4 spaces left
£1,597£1,372
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Saturday Sep 12, 2026
Saturday Sep 19, 2026
Trip size max: 11 - 4 spaces left
£1,603£1,377
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Tuesday Sep 22, 2026
Tuesday Sep 29, 2026
Trip size max: 11 - 2 spaces left
£1,603
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Saturday Sep 26, 2026
Saturday Oct 03, 2026
Trip size max: 11 - 4 spaces left
£1,553£1,335
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Tuesday Oct 06, 2026
Tuesday Oct 13, 2026
Trip size max: 11 - 5 spaces left
£1,553£1,335
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Tuesday May 04, 2027
Tuesday May 11, 2027
Trip size max: 11 - 11 spaces left
£1,581
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Saturday May 08, 2027
Saturday May 15, 2027
Trip size max: 11 - 9 spaces left
£1,581
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Tuesday May 18, 2027
Tuesday May 25, 2027
Trip size max: 11 - 11 spaces left
£1,581
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Saturday May 22, 2027
Saturday May 29, 2027
Trip size max: 11 - 11 spaces left
£1,581
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Tuesday Jun 01, 2027
Tuesday Jun 08, 2027
Trip size max: 11 - 11 spaces left
£1,636
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Saturday Jun 05, 2027
Saturday Jun 12, 2027
Trip size max: 11 - 11 spaces left
£1,636
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Important notes
Reviews (164)
5 stars
150
4 stars
8
3 stars
2
2 stars
3
1 star
1
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Oscar
Jul 25, 2026
An incredible way to see the Greek islands, we got to see beautiful parts of the Cyclades that most people don’t experience. Our guide Lukas was a big part of why this trip was so good. He made sure we were safe and had a great experience.
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Kate
Jul 25, 2026
Such an incredible trip! The skipper Lukas made it an unbelievable experience taking us to so many hidden gems and teaching us about Greece’s history. The variety of islands we visited both popular and not so well known was the perfect balance! Trip of a lifetime!
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Lachlan
Jul 25, 2026
Lukas is the best! Great guy and skipper + took us to some great destinations. I highly recommend this tour.
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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!
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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
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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! ⭐⭐⭐⭐⭐
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James
Jun 29, 2026
Nikolas has great local knowledge and was an amazing skipper
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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!
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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.
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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!!!