78 Sailboats to Rent in Cyclades

Sailboat charter in Cyclades

3 Reasons to charter a Sailboat in the Cyclades Islands

Breathtaking Scenery

Greece is a country of gorgeous sandy coastlines, volcanic rock, mountains, valleys and lush greenery, and a sailing holiday in the Cyclades is a great way to see a bit of everything. When you charter a sailboat in Santorini, you will have the chance to visit the incredible caldera, where you can learn about the island’s volcanic history and you will be met with awe-inspiring views! If you navigate the waters of Folegandros, moor your boat and head to Chora, the capital, a town located atop a 200m high cliff. Or stop off at Kynthos to visit Kolona Beach, where a beautiful strip of fine golden sand stretches between the main island and Agios Loukas islet, so you can sunbathe with the sea on either side of you!

Captivating History

Ancient archaeological sites, medieval towns, world-renowned remains… the Cyclades have it all and are a great spot for any historian. The archipelago is home to the famous island of Delos, which is one of most important mythological, historical and archeological sites in Greece, known as being the birthplace of both Apollo and Artemis. If you begin your sailboat charter in Naxos, pay a visit to the ‘Portara’ before setting sail; otherwise known as the ‘great door’, this is the only remaining part of a temple which dates back to 530 B.C. Or drop anchor at Santorini, and head to the Ancient Thera, where you will not only be inspired by its fascinating history, also by the enchanting panoramic views of the azure ocean which surrounds you.

Seductive Santorini

Santorini is arguably the best-known island of the Cyclades; famed for its white, sugar-cube buildings which cloak the hillsides, and blue-domed churches, it’s a picturesque vision of Greek island life! Sumptuous cuisine, luxury resorts, pristine beaches and postcard-worthy sunsets are just a few things which give Santorini its reputation as a romantic haven. But the island also has other wonders worth exploring if it’s a potential anchorage during your sailboat charter; visit the breathtaking Red Beach, where sheer red and black volcanic rocks tower over a thin strip of sand. Or if you’re looking for nature or active ways of discovering the island, you can climb Profitias Ilias mountain, or hike a 3-hour route from Fira to Oia, through charming little hillside villages, and with impressive views of the caldera.

Sailing Conditions

The Cyclades are a fantastic destination for a sailboat charter if you’ve got a few years of experience behind you, as due to the force of the Meltemi winds, navigation has the potential to be a little less predictable as winds and waves can be stronger; a fun challenge for some but not for the inexperienced! But this by no means should stop any beginners from venturing here for a cruise, just perhaps opt for a skippered rather than bareboat charter.