Best Greek Islands to Charter a Sailboat

If there’s one European country that must be a part of every person’s travel bucket list, it should be Greece. With dozens of heritage sites, rich history, abundant culture, Greece welcomes hundreds of thousands of tourists every year. One of the reasons why people flock to Greece is its pristine waters and stunning islands. Some may visit these islands using commercial boats or good ol’ planes. However, only a few people know that the best way to roam around these scenic wonders is by sailboat.

If sailing in Greece is something that you want to try, this article is for you. We have compiled a list of the best islands to charter a sailboat in Greece.


Your visit to Greece will never be complete without dropping by the island of Santorini. Considered to be the most popular spot in the country, Santorini showcases a spectacular scene of colorful houses, restaurants, and ancient site draping in the sides of the mountain. To appreciate the beauty of this majestic place, it is best to sail about across the crystal clear waters of the Aegean Sea. From the sea, you will be able to witness this natural wonder believed to have been formed from the eruption of several volcanoes in the area.

Sailing in Santorini will create a lot of memories that you will never forget. There are shipping companies that offer a guided sailboat while enjoying sumptuous Greek cuisine. To top it all off, you have the amazing view as your backdrop. Can anything be more romantic than that?


If you are looking for an island with the perfect fusion of beach, nightlife, and Cycladic villages, Sifnos is the best island for you. Just a few hours of travel from the Greek capital, this island is home to a rich culture with picturesque sceneries that most tourists are dying to witness. Of course, the best part of discovering this island is by cruising along the Bay of Kamares. Here, you get to appreciate the postcard-perfect view of the Sifnos village draping along the side of the mountains. Its pristine waters and powdery sand gives the perfect ambiance for people who wanted to have sun-kissed skin.

Once your sailing is done, grab a bite from the restaurants nearby and discover why Sifnos is considered as the island of flavors. You may also take advantage of the chance to visit over 200 churches and unique traditional villages located on this stunning island.

If you are sailing around Sifnos, consider making a detour to visit the nearby Milos. This wonderful island is often overlooked by tourists, all the better for those who do wander there. The island has some of the best selections of beaches of all Greek islands, plus amazing seafood and a significant place in archaeology – it is the place of discovery of both the famed Venus de Milo as well as Asclepius of Milos. Since Milos is not as popular, you can explore it in relative solitude compared to the likes of Santorini and Sifnos.

The Dodecanese Islands

If the first two islands are not enough for you, why not explore the historic Dodecanese Islands. As the name suggests, it is made of 12 larger islands with 150 smaller islands all lying in the Aegean Sea. This unique collection of islands is best reached by chartering a sailboat. Best done during summer, sailing is more fun in Dodecanese Island where you get to enjoy the dramatic scenery of this historic island from the sea.

Its largest island, Rhodes, has small villages along the coast of its beach resorts that adds up to the beauty of the place. The rocky hills and bluish waters add to the exquisiteness of the island. Hence, it is not surprising that it is part of every sailor’s dream destination. Finally, you may also want to explore the island of Kos that takes pride in its long strips of white sand beaches, scenic landscapes, and ancient ruins.

Greece has a lot of secrets that need to be discovered. Moreover, its beauty its beauty is best seen from its cam and pristine waters. So what are you waiting for? Cruise along Greece and discover its grandeur like you’ve never seen before.

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