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Sailing in the Cyclades isles of Greece

Port of departure: Mykonos, Greece
1,040€ Per personFull boat
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1,040€ 6,355€
Per person
Full boat
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Contact the skipper to arrange an outing.
The coordinator: Iwona
3 reviews
Explore the Cyclades in the most amazing way possible, hopping from island to island by sailboat. Take in the views, swim and enjoy the local food. One island after the other will be your new favorite as you travel with new friends and make new memories.
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Activity dedicated to
  • Vacation on the water
There are two possible itineraries for this trip. You may book two weeks in a row to experience both, but they are equally incredible trips!

Departure from Mykonos on Saturday


Mykonos: This unique and traditional island is one of the most popular islands in the Aegean Sea. It is truly paradise with its beautiful beach, delicious food, fun shopping and great nightlife.

Naxos: The largest of the islands, Naxos will fascinate you with its culture. Stroll down the winding back streets and be sure to visit some of the artisan boutiques and, if you’re a foodie, don’t miss the great family run restaurants here.

Koufonisi: Koufonisi is the smallest island in the Cyclades and has absolutely breathtaking natural beauty. Go for a dip in the crystal clear waters and take in your surroundings.

Santorini: One of the most well known and photographed places in the Mediterranean Sea, Santorini is a must-see destination. Sail through the caldera and enjoy our time to relax in Santorini.

Ios: Here you will find an exciting alternative scene and no shortage of backpackers. Ios is also known for its water sports beaches and being the supposed location of the tomb of Homer! Explore and little and enjoy the different atmosphere that Ios has to offer.

Paros: This charming spot on the north of the island might just be our favorite. Relax at one of the many bars and look out over the beautiful fishing harbor as the sun goes down.


Mykonos: A hub for arrivals and departures, you can never get enough of Mykonos. With its incredible photo opportunities, awesome nightlife and beautiful beaches, you won’t want to move on to the next port!

Paros: Our stop here will likely be in Parakia, south-west of Mykonos. If you love history and exploring, find yourself at the Church of 100 doors, the meeting point of Christianity and Greek mythology.

Schinoussa: Also known as the Island of the Sun, Schinoussa is a tiny but wonderful island to stop for a night. Go on one of the beautiful hiking trails and take advantage of the delicious local cuisine.

Santorini: This iconic island still has an active volcano! Travel up to the town of Thera and find yourself right on the edge of the caldera. Don’t miss out of the locally grown vegetables in the restaurants - they are truly amazing.

Folegandros: Enjoy a moment on this relaxing island where you can enjoy some peace and quiet. See an unbelievable view of the Aegean if you’re willing to take a trip up to Chora.

Piso Livadhi: This small harbor and town, located on Paro, is incredible charming and pleasant to explore. Sit back at one of the little restaurants and enjoy a glass of ouzo with your locally-caught dish.
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Included in the price
  • Insurance
  • Final cleaning
  • Costs of mooring and anchoring
  • Professional skipper
  • Bed linens
  • Gas
  • Paddle Surf
  • Tender
  • Tourism taxes
Not included in the price
  • Food and drink on land
  • Airport transfer
  • Flights
Additional information
The plan shown above is indicative of the islands you will likely visit on this holiday. On this holiday, you will be accompanied by a professional skipper and 1st mate who want to make your holiday as perfect as possible. The true itinerary and order of stops is up to the skipper and may change due to weather. The crew will keep you informed for the plan each day.

Each cabin is shared between two people. The price per person may be different depending on the cabin you purchase. The other prices per person are below:
A spot in a private double or twin cabin with ensuite shower/ WC is 1040€ (2 weeks is 1885€)
A spot in a private twin cabin with shared ensuite shower/ WC is 994€ (2 weeks is 1765€)

Required single supplement for solo travelers: 650€ (2 weeks is 1195€)

A continental buffet breakfast and light lunch is included daily, as well as most other expenses (including gas, moorings, insurance), but other snacks and meals eaten ashore are not included.

There are two yachts sailing for each date shown, each with 4 cabins.

You will be sailing on either a Ocean Star 51.1 or a Sun Odyssey 52.2.
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Mykonos, Greece
Greek Islands
Meet Iwona, the coordinator
3 reviews
Iwona has not yet written their biography
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3 reviews
  • Sailing in the Cyclades isles of Greece
    David Faries
    March 2019
    Can’t speak highly enough of them.
    We’ve just booked our 9th flotilla with them. Our first was back in 2012 when our children were young.
    The customer service focus of all staff is evident from the start, from the booking/admin (special mention for Suzie, Senior Consultant!) through to the sailing experience on the holiday.
    One of the directors even joined one of our flotillas for a couple of days (a newish route with the complications of going through customs) and sought the views and comments of the customers. Recent tweaks to routes and itineraries shows that feedback is acted upon.
    Their Skippers and First Mates are excellent. Experienced, knowledgeable and friendly, decisive and supportive when they need to be (if/when conditions become challenging), nothing is too much trouble (special mentions for Wendy, Simon, Sam and George! I could go on!)
    The flotillas provide a great mix of locations, structured but flexible routes, with a day or two free sailing if you want to explore on your own. Whether you’re a couple on a small boat, a family with children or a group of friends on a large boat, all needs are catered for.
    I would have not hesitation in recommending them. We wouldn’t use anyone else!
  • Sailing holiday for a week in the Ionian Islands
    Sarah Kendall
    March 2019
    Have sailed seven times with them to some wonderful places, always good value, nice boats and enthusiastic leaders (except one who was a miserable oddity). We were very nervous on our first trip with a 40 foot boat but the leader put us at ease and since then we have always returned to sail with them.
  • Sailing in the Cyclades isles of Greece
    Adrian Bucos
    May 2018
    A perfect week. Excellent boat ,accommodation and training conditions, the best trainer I ever had and a very competent flotilla management. Nice country, nice places, nice people, nice memories to keep. Quite an experience.
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