Original
Sailing
Sail Greece: Santorini to Mykonos
4.8
Excellent
circle139 reviews
location_on 8 days
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Start
Santorini, Greece
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Finish
Mykonos, Greece
tour
Trip Code
ZSRR
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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 £1,162(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
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Spend your days island-hopping in the Cyclades, swimming in the clear waters of the Aegean Sea and sleeping aboard a private yacht.
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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.
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Break bread with locals in the sleepy fishing villages of the Small Cyclades islands, away from the typical tourist trail.
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Taste rural life on the large island of Naxos – a great mix of historic neighbourhoods, gorgeous views and tasty Kitron liqueur.
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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?
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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.
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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.
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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 sunscreen 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 the Greek Islands between Santorini and Mykonos
- DAY 1Day 1 • Santorini – Ios
- DAY 2Day 2 • Amorgos
- DAY 3Day 3-4 • Small Cyclades
- DAY 4Day 5 • Naxos
- DAY 5Day 6 • Syros
- DAY 6Day 7 • Mykonos
- DAY 7Day 8 • Mykonos
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 Jul 21, 2026
Tuesday Jul 28, 2026
Trip size max: 11 - Sold Out
Saturday Jul 25, 2026
Saturday Aug 01, 2026
Trip size max: 11 - 2 spaces left
£1,372
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Tuesday Aug 04, 2026
Tuesday Aug 11, 2026
Trip size max: 11 - 1 space left
£1,372
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Saturday Aug 08, 2026
Saturday Aug 15, 2026
Trip size max: 11 - 1 space left
£1,438£1,304
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Tuesday Aug 18, 2026
Tuesday Aug 25, 2026
Trip size max: 11 - 4 spaces left
£1,438£1,169
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Saturday Aug 22, 2026
Saturday Aug 29, 2026
Trip size max: 11 - 5 spaces left
£1,372£1,180
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Tuesday Sep 01, 2026
Tuesday Sep 08, 2026
Trip size max: 11 - 6 spaces left
£1,619£1,162
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Saturday Sep 05, 2026
Saturday Sep 12, 2026
Trip size max: 11 - 6 spaces left
£1,702£1,300
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Tuesday Sep 15, 2026
Tuesday Sep 22, 2026
Trip size max: 11 - 4 spaces left
£1,520£1,307
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Saturday Sep 19, 2026
Saturday Sep 26, 2026
Trip size max: 11 - 3 spaces left
£1,520
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Tuesday Sep 29, 2026
Tuesday Oct 06, 2026
Trip size max: 11 - 7 spaces left
£1,520£1,164
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Saturday Oct 03, 2026
Saturday Oct 10, 2026
Trip size max: 11 - 10 spaces left
£1,520£1,164
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Saturday May 01, 2027
Saturday May 08, 2027
Trip size max: 11 - 11 spaces left
£1,542
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Tuesday May 11, 2027
Tuesday May 18, 2027
Trip size max: 11 - 11 spaces left
£1,542
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Saturday May 15, 2027
Saturday May 22, 2027
Trip size max: 11 - 11 spaces left
£1,542
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Important notes
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START TIME
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This trip starts on Day 1 in Santorini at 1pm.
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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 Essential Trip Information for joining and finishing points.
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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 (137)
5 stars
124
4 stars
8
3 stars
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1 star
3
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David
Jul 04, 2026
Wonderful experience sailing around the Cyclades with Captain Nikos. Enjoyed the experience of being part of a small group on a well equipped sailing boat. Had strong winds to no winds and everything in between. Nikos taught us a lot about Greece, its culture and history and its people. It’s a nice outdoors tour with swim stops everyday and sailing each morning and visiting islands in the late afternoon and evenings. Made a new set of great friends that we shared the travel and swimming and dining with. Great fun.
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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!
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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.
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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.
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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!
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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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Autumn
Jun 02, 2026
Sailing around the islands was a great way to experience Greece. Being in a small group, there was no feeling like cattle the way large tours feel. We saw lots of spots bigger cruise ships would never get to and were our favorite sights. It is a sail boat so rooms are tight but if you're prepared for that, you'll have a great time!
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Ian
Jun 01, 2026
Outstanding experience of sailing the Greek Islands in a spacious and comfortable yacht, led by a highly experienced and professional skipper, This was none of my favourite and most memorable holidays.
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Jochen
May 28, 2026
Loukas is the best skipper you could imagine. Thoughtful, competent, funny, compassionate. We felt safe and learned a lot about Greece, its people ... and sailing.
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Karen
May 26, 2026
What an amazing trip this was. It was wonderful sailing to the various islands and visiting smaller villages, historical sites and experiencing the wonderful food. The trip was well organised and our skipper, Stylianos, amazing!