Original
Sailing
Sail Greece: Mykonos to Santorini
4.9
Excellent
circle159 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 £1,092(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 Jun 30, 2026
Tuesday Jul 07, 2026
Trip size max: 11 - Sold Out
Saturday Jul 04, 2026
Saturday Jul 11, 2026
Trip size max: 11 - Sold Out
Tuesday Jul 14, 2026
Tuesday Jul 21, 2026
Trip size max: 11 - 2 spaces left
£1,267
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Saturday Jul 18, 2026
Saturday Jul 25, 2026
Trip size max: 11 - 4 spaces left
£1,471£1,196
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Tuesday Jul 28, 2026
Tuesday Aug 04, 2026
Trip size max: 11 - 4 spaces left
£1,267£1,092
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Saturday Aug 01, 2026
Saturday Aug 08, 2026
Trip size max: 11 - 6 spaces left
£1,471£1,127
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Tuesday Aug 11, 2026
Tuesday Aug 18, 2026
Trip size max: 11 - 1 space left
£1,581
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Saturday Aug 15, 2026
Saturday Aug 22, 2026
Trip size max: 11 - 4 spaces left
£1,509£1,297
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Tuesday Aug 25, 2026
Tuesday Sep 01, 2026
Trip size max: 11 - 2 spaces left
£1,581£1,581
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Saturday Aug 29, 2026
Saturday Sep 05, 2026
Trip size max: 11 - 5 spaces left
£1,482£1,135
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Tuesday Sep 08, 2026
Tuesday Sep 15, 2026
Trip size max: 11 - 2 spaces left
£1,597
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Saturday Sep 12, 2026
Saturday Sep 19, 2026
Trip size max: 11 - 3 spaces left
£1,603
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Tuesday Sep 22, 2026
Tuesday Sep 29, 2026
Trip size max: 11 - 1 space left
£1,603
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Saturday Sep 26, 2026
Saturday Oct 03, 2026
Trip size max: 11 - 9 spaces left
£1,553£1,116
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Tuesday Oct 06, 2026
Tuesday Oct 13, 2026
Trip size max: 11 - 5 spaces left
£1,553
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Important notes
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START TIME:
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The trip commences on day 1 in Mykonos at 4pm.
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ACCOMMODATION ON BOARD THE YACHT
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This trip is accommodated entirely on board a yacht of between 54ft to 56ft. The yacht can accommodate up to 11 traveller’s in the following cabin types:
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double bed cabins (x2)
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twin bunk bed cabins (x2)
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triple bunk bed cabin (x1)
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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. Everyone including the skipper shares the bathrooms on board.
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Solo customers can choose to book either a twin bunk bed cabin or a triple bunk bed cabin and will be matched up with other solo customers of the same gender. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge when booking either a twin or double cabin.
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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. If you are booking a bunk bed cabin you must be willing to sleep on the top bunk.
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Double bed cabins can only be booked by 2 people travelling together or a solo customer who pays for a single supplement.
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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.
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HOT WEATHER:
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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.
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PASSPORT DETAILS:
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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.
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ADDITIONAL ACCOMMODATION:
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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.
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TRIP KITTY:
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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 (152)
5 stars
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4 stars
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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!!!
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Richard
Jun 13, 2026
The sailing trip from Mykonos to Santorini was an amazing experience. I have done lots of travel, including adventure travel, but I can honestly say this was up there with the best travel experiences I have had. The azure, nearly indigo waters of the Aegean Sea, golden sandy beaches, burnt dry hills, and interesting architecture and incredible food all made the trip an unforgettable experience. Our guide, Nikolas, was informative, humorous, and an extremely good sailor, which all made for a very enjoyable trip. I will definitely be back for another Intrepid trip as soon as the opportunity arises.
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Doni
Jun 13, 2026
Thoroughly enjoyed my Intrepid sailing trip through the Greek Cyclades and every day exceeded my expectations. I’ve been to some pretty amazing places and thanks to Intrepid and Captain Nikolas, Greek Cyclades ranks as one of the best, most memorable trips I’ve taken. The food, culture, sites people, and all hospitalities of Intrepid were first class
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Michaela
Jun 10, 2026
I greatly enjoyed my trip from Mykonos to Santorini! The islands we visited were stunning with a perfect mix of busy towns and quiet beaches. There were lots of swimming opportunities when I went in June. The skipper, Ilias, was fantastic - he gave us thorough recommendations of things to do on the islands and was always willing to answer the many questions we had about sailing and life in Greece!
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Rosalind
Jun 02, 2026
I would highly recommend this sailing trip. Lukas was an excellent skipper and looked after us well. He made great recommendations for local restaurants. It was a good introduction to the Greek islands, including bigger and smaller ones. Had a great time. The cabins are clean but small.
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Liam
May 30, 2026
Trip was fantastic, highly recommend. Ilias was an amazing captain/leader, and his knowledge and experience made the trip what it was!
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Zenta
May 30, 2026
Well mesured sayling swimming sightseeing food tasting experience you just take it in with open heart! Thanks to George's charismatic leadership we enjoyed beautiful places and tasted amazing food listening to his stories about each island .And Stelios - new skiper was also very helpful and kind! We were able to participate to put up the sail and helm the boat.As being responsible - we made u turn once to pick up plastic bottle for what we were awarded by Poseidon to see the delphins 3 times!
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Johh
May 21, 2026
The Mykonos to Santorini sailing trip exceeded my expectations . It is the ideal way of visiting the islands in a relaxed way and allowing access to otherwise inaccessible beaches and places . Fortunately the skipper was able to bring together a multinational group of tour members to enhance the experience and his local knowledge of both places of interest and eating options on each island was brilliant. Bearing in mind this was a sailing trip don't think the experience could be beaten
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STEPHANE
May 20, 2026
Excellent experience: sailing à wonderful yacht under the leadership of an Excellent skipper in stunning places in the compagny of wonderful people.
Weather and winds were fine.
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Paul
Oct 06, 2025
Our Greek islands sail was the highlight of our Europe trip. George our skipper made the trip fantastic.