Dodecanese Islands Yacht Charter Guide

The Dodecanese – Where Stunning Scenery & History Await

The Dodecanese Islands offer one of Greece's most rewarding yacht charter destinations. Scattered across the south-eastern Aegean Sea close to the Turkish coast, this fascinating island group combines spectacular scenery, rich history and authentic Greek island life. While destinations such as the Cyclades and Ionian Islands attract the largest crowds, the Dodecanese remains a little more off the beaten track, rewarding sailors with charming harbours, welcoming villages and a relaxed cruising atmosphere.

Most yacht charters begin from Kos, the region's principal charter base, although Rhodes is also an excellent departure point with convenient international flight connections. From either base, you'll enjoy a varied itinerary of short coastal passages and island hops, with each destination offering its own unique character and attractions.

The Dodecanese generally enjoys excellent sailing conditions. Although the Meltemi winds can still be fresh during the height of summer, the nearby Turkish mainland provides some protection compared with the more exposed Cyclades, making conditions enjoyable for both experienced sailors and many competent bareboat crews.

With more than twenty inhabited islands to explore, there is no shortage of memorable destinations. Wander through the colourful harbour of Symi, visit the medieval streets of Rhodes, discover the spiritual heritage of Patmos, or enjoy the peaceful anchorages of smaller islands such as Lipsi, Tilos and Chalki. Every stop offers a different blend of history, culture, local cuisine and natural beauty.

Given the close proximity of Turkey, some sailors consider combining both countries in a single charter. While this is possible with jurisdiction and operator approval, we generally recommend enjoying the Dodecanese as a destination in its own right. Greece and Turkey each offer distinct sailing experiences, and both deserve the time to be explored properly. If you'd like to discover both, a separate charter from the Turkish base of Fethiye can be an excellent complement to a future Greek sailing holiday.

Whether you're planning your first Greek yacht charter or returning to explore another corner of the Aegean, we can help you select the right yacht and design an itinerary that makes the most of your time in this remarkable cruising region.

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