Sail the Cyclades

Charter your Own Boat and Get Away from the Crowd

The Cyclades offer the quintessential Greek island holiday, and tourists by the thousands take the ferry from Athens each season. The group comprises some 220 islands with countless places to explore from a charter yacht and great sailing between. With so many stopover options to choose from in the Cyclades, it pays to do the research and get the best advice you can.

If sailing is your passion, the Cyclades is your place. Enjoying the freedom of travelling under sail across the sparkling Aegean to the next wonderful Greek island, is an experience that visitors by ferry can only imagine. Once there, glide past the breakwater for your place on the quay. Tie up, relax, explore and wait for the evening to come alive. Another great day of charter boat vacationing in Greece.

The best-known islands in the Cyclades group include Mykonos, Paros, Syros and Santorini. This is a compact group in the area of the Aegean Sea to the east of Athens, making these the most popular of Greek island sailing waters.

The voyage to and from Cyclades waters provides great sailing, as much a part of the adventure as the island-hopping itself. And with so many options to consider on arrival, each day you can do as much or as little sailing as you wish. 

Our client reviews about charter sailing in Greece

Rating: 5 / 5
The Lagoon 46 was the best catamaran we have chartered. There was plenty of deck and seating space and all the bedrooms/ensuites were a good size.

Preveza was a great starting point and we enjoyed travelling south to Ithaki and north to Paxi. Kalamos was a highlight we tied up to a pier next to a taverna for the night and it was a lovely spot.

We had very good service from Robert and Sue at Yachting Holidays and dealing with an NZ company gave us peace of mind. The service from Fyly in Greece was also excellent. We really appreciated being able to board the boat early and our skipper was also very friendly and easy to get along with.

Our skipper Adrian Dimitru was keen to get away on Saturday afternoon so we headed south and got a day ahead which was great. .he cruise was excellent and Adrian got us to some of his favourite spots so we were very lucky.

Ithaki not to be missed. Craig, New Zealand, Oct 18th, 2023
Rating: 5 / 5
Dear Sue, we would like to thank you and Robert for all the work you put in to make our charter run so smoothly from your end. We absolutely loved the Greek Islands, they were everything we had ever imagined. Jill and Pip, New Zealand , Oct 9th, 2019
Good breezes that provided just the right level of challenge. Not super crowded - no troubles berthing / mooring / eating / etc. Fairly chilled - at least compared to Croatia. Patmos was very good. John, Australia, Aug 17th, 2019
Had a great time. The wind was terrific - good fun, but nothing too hairy - exactly what we were looking for to take it up a notch or two from Croatia last year. And the Dodecanese were really good - nice ports, not too crowded (esp compared to Croatia) - just felt a bit more out of the way. DYC were fine - a little bit more on the 'smell of an oily rag' end of things compared to the very efficient German-run scene at Trogir, but it all worked and no real issues. Excellent recommendation Robert - boat and destination - you nailed it!

John, Australia, Jul 31st, 2019
The Lucky Clover was fantastic. We travelled around the Saronic Islands which were beautiful. A new adventure every day. One day we hired scooters and explored the islands. Great service thank you. 10 out of 10, a trip of a lifetime! Deborah, New Zealand, Aug 1st, 2017
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