Cyclades Yacht Charters | Sail Greece's Iconic Islands

The Cyclades – Greece's Iconic Island Sailing Adventure

The Cyclades are the quintessential Greek island sailing destination, where whitewashed villages, crystal-clear waters and dramatic landscapes combine to create one of the Mediterranean's most memorable yacht charter experiences. Travelling by yacht allows you to experience these famous islands at your own pace, escaping the ferry crowds and discovering secluded bays, traditional harbours and hidden beaches that many visitors never see.

Scattered across the sparkling Aegean Sea to the southeast of Athens, the Cyclades comprise more than 200 islands and islets, each with its own distinctive character. From cosmopolitan Mykonos and spectacular Santorini to the charming harbours of Paros and Syros, every island offers something different. With so many cruising options available, careful itinerary planning is worthwhile, allowing you to balance enjoyable sailing passages with time ashore exploring villages, beaches and local tavernas.

For keen sailors, the Cyclades offer some of the finest sailing in Greece. Reliable summer winds, open-water passages and rewarding island-to-island cruising make this a region best suited to crews with reasonable sailing experience or those choosing a professional skipper. Every day's voyage is part of the adventure as you sail across the deep blue Aegean towards another beautiful island waiting to be explored.

Approaching an island harbour under sail is an experience few ferry passengers ever enjoy. Ease into a traditional waterfront port, secure the yacht on the town quay, then spend the afternoon wandering narrow laneways, discovering local cafés and soaking up the relaxed rhythm of island life. As evening falls, waterfront tavernas come alive, offering fresh seafood, regional wines and the warm hospitality for which the Greek Islands are renowned.

Many charters begin from Athens, making the journey to and from the Cyclades an integral part of the sailing adventure. Alternatively, you can embark from one of the regional island charter bases and immediately immerse yourself in the heart of the archipelago. With countless islands, anchorages and cruising routes to choose from, the Cyclades offer the flexibility to sail as much or as little as you wish, creating a yacht charter tailored entirely to your crew and your style of holiday.

For sailors seeking classic Greek island cruising, few destinations compare with the Cyclades. Combining world-famous islands, exceptional sailing conditions, spectacular scenery and authentic Mediterranean culture, this remarkable archipelago remains one of the world's premier yacht charter destinations.

The map below has been produced using internet tools and pin placements may not be exact. It is intended as a rough a guide. For further research and preparing itineraries, we suggest you refer to quality on-line maps and charts.

Our client reviews about charter sailing in Greece

Rating: ★★★★★
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: ★★★★★
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: ★★★★★
(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: ★★★★★
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: ★★★★★
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