For 18 months, we sailed across the Mediterranean Sea. From the coast of Israel all the way to Spain, anchoring in Cyprus, Turkey, Greece, Italy and France. We sailed both winter and summer, enjoying the quiet shoulder seasons and the bustling sailboat charter high seasons. Each one of the places we have been lucky to visit is unique, but only a few places made our "Best sailing holiday destinations in the Mediterranean Sea" list.

Best Sailing Holiday Destinations in the Mediterranean Sea

Turquoise Coast, Turkey

We have to admit we were completely unaware of this coastline before we entered Turkey. But luckily many of you recommend this sailing route and what a pity it would have been if we would have missed this sailing destination. Located on the Teke Penisula between Marmaris and Antalya, this strip of land offers the best of Turkey. Small rocky bays, long sandy beaches and ancient ruins, all framed by jade water and forest-blanketed slopes.

Does this already sound perfect? We did not tell you the best part yet! The whole area is equipped perfectly for sailboats! Most small bays host a restaurant with a dock or mooring balls for the night. Every bigger city has well equipped marinas for winter moorings or troubleshooting during your sailing holiday. So whatever you like it cozy and small in a bay or loud and big in a city, this strip of land offers it all, while permitting you calm sailing days and a splash in turquoise waters.

Isola Asinara, Italy

This island it unique in so many ways. It's history, the "inhabitants", the landscape and more. It has a dark history of pain and illness, but today it features one of the biggest national parks. You are not allowed to anchor anywhere, but buoys have been placed along the coast and can be booked and rented cheaply online. The sleepy island will reward you with breathtaking nature, peaceful evenings and great snorkelling and diving spots. If you want to discover more about this unique island in the north of Sardinia, check out our Vlog.

Kalymnos, Greece

Are you looking for the right mixture of land and sea for your sailing holiday? Then don't look any further. The greek islands Kalymnos offers both magnificent bays for anchoring or marinas for safe mooring and steep cliffs to climb or mountains to hike. 

Only located a sailing day away from Kos Marina, where you can charter a sailboat, this Island will keep you busy all week long. Prefer a beautiful sailing day and a splash into the crystalline water? You find it here. Prefer a lazy stroll through narrow streets in the town. You will find it on this Island. Prefer hiking up the mountains or even climb the steep rocks falling into the sea? You will find plenty of possibilities here for a perfect sailing holiday.

Cala Macarella, Spain

Menorca is the least "famous" of the Balearic Islands, but it is our favourite. Followed closely by Formentera. However, while Formentera features a stunning beach strip, Menorca has the whole package for a sailing holiday. Cute little towns wedge between cliffs, Spanish food you will dream of long after you return home and picture-perfect bays.

Our favourite bay is definitely Cala Macarella. If you sail there during high season be prepared to share the bay with many other boats and beachgoers. The turquoise water and white beaches call to many, but this little bay also holds some epic free-diving spots. Caves and passages riddle the whole land structure of Menorca. We spent days exploring the cliffs and had our first and best cave freedive in Cala Macarella.

Gallipoli, Italy

This place has no steep cliffs like Kalymnos and no ancient ruins like the turquoise coast, but it is still our favorite place. Why? The incredible watercolor! You can literally find all shades from deep blue to turquoise to crystal clear by just rowing in your dinghy from your sailboat to shore. I simply have to admit that my words won't be able to describe this place and that also the pictures fail to transmit the beauty we were able to see there. So please, if you ever have the chance to sail there do and enjoy the spectacular views given by nature (and obviously the fantastic cuisine of the town :) ).