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Sail the Cyclades

Charter your Own Boat and Get Away from the Crowd

The Cyclades offer the quintessential Greek island holiday, drawing thousands of tourists each season who take the ferry from Athens. This group comprises around 220 islands, each with countless places to explore by charter yacht, along with exceptional sailing between them. With so many stopover options available, it’s worth doing the research and seeking expert advice to make the most of your time in this beautiful region.

For sailing enthusiasts, the Cyclades is a dream destination. The freedom of traveling under sail across the sparkling Aegean Sea to the next idyllic Greek island is an experience that ferry passengers can only envy. Once you arrive, glide past the breakwater to your spot on the quay, tie up, relax, explore, and wait for the evening to bring the island to life. Another perfect day of charter boat vacationing in Greece.

The most well-known islands in the Cyclades include Mykonos, Paros, Syros, and Santorini. This compact group lies to the east of Athens in the Aegean Sea, making it one of the most popular sailing destinations in Greece.

The journey to and from the Cyclades is an adventure in itself, offering fantastic sailing as part of the experience. And with so many island options to explore upon arrival, each day offers the flexibility to sail as much or as little as you wish.
 
 
 
 
 

Our client reviews about charter sailing in Greece

Rating: 5 / 5
Boat had plenty of space for the 7 of us. The sleeping cabins were well appointed and clean as were the communal areas.

The skipper Socarates took us to pristine beaches and bays that were not overrun with other boats. Loved being able to sail during the day and then visit the local towns at night. The skipper always gave us recommendations and asked what we would like to do each day. Crew were totally there to make our trip comfortable and to experience the beautiful Greek islands

The booking experience with Sail Connection was good would recommend to friends wanting to charter a boat. Anna, Australia, Oct 2nd, 2024
Rating: 5 / 5
Boat was fantastic - was it's first charter so perfect condition. We sailed around Ithica and Kefalonia - both islands were beautiful. Sail connections was easy to deal with. Kurt, Australia, Jul 12th, 2024
Rating: 5 / 5
(The boat was) perfect for our family of four. Only slight negative is that the helm position has a fairly large blind spot and there is no shade.
Favourite spot ... Sarakiniko Beach, Ithaka. This beautiful spot offered good anchorage, a local taverna and easy access over the hill to Vathy.
(Your service was) excellent. Dimitri in particular was very accommodating and nothing seemed to be a problem.
Stephen, Australia, Jul 8th, 2024
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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