Sail Greece with an expert

Personal service since 2010

SailwithGeorge offers carefully crafted skippered sailing holidays for private groups. Operating in Cyclades, Argosaronic and Ionian sea with weekly departures. Unparalleled comfort on company-owned  large 56ft sailing yachts. A very personal service by George and his heart driven crew, made in Greece by Greeks, a very different uncompromised sailing holiday experience for everyone.

More than 2300 people have sailed with George

98% of our client base are 5-star happy with our service
Read what they say about us

Quality time onboard

It is about you and making the most out of your sailing holidays! That early morning swim in the perfect secluded bay, that sunset relaxing walk on the greek ancient trails, the perfect timing for the most delicious Greek dinner, the best use of the day for endless swimming time.

The result is an uncompromised sailing holiday which is what keeps our community growing and people keep coming back.

Whether you are travelling solo or with your partner on one of our shared departures or with family and friends on our private trips, we are committed to make the extra step, treat you as our only customer and make sure you get back home with unforgettable memories from your summer in Greece.

Our Fleet & Skippers

Private or shared?

Private Tailor Made

Everyone, Private 
Tailor made routes & dates
Optional activities
Max group size: 11persons
Book a whole boat

Booking a whole boat

Plan your own skippered sailing holidays on your dates, route and style. We  will make it happen, coming up with lots of recommendations to make the most out of it. One-way charters, remote deliveries of crew with motorboat and custom-made activities. Inquire now

Check-in/out place flexible


To be quoted as per your inquiry

Happy Family, 7days

Any family, Private 
Suitable for any family with children
Max group size: 11 persons
Book a whole boat

Booking a whole boat

Happy children means happy parents. And children to be happy during holidays they need to play, try new stuff, explore. This is a child-friendly sailing week around the breath-taking Greek islands, which will leave unforgettable memories for all the family. Inquire now

Departs Athens or Cyclades, from 


To be quoted as per your inquiry

Share & Sail, 7days

Everyone, Shared departure
Friends of all ages
Max group size: 11 persons
June-Oct, check available departures
Book a berth or a cabin

Booking a berth or cabin

Solo travellers, couples or small group of friends, on an unforgettable sailing week, full of swimming, relaxing, sailing and optional activities on land. Departures are guaranteed regardless of bookings. Such a great way to enjoy in the heart of Cyclades. Check dates

Departs Syros island, from 


per person, per week

SailwithGeorge in Greece

Get in contact

Our Fleet

The most versatile and seaworthy charter yacht ever built
3 available

Ocean Star 56

Our yachts are true sailing boats with uncompromised comfort for any group. Ample space in the very wide interior, unparalleled privacy in a unique layout of 5cabin/5WCs for 11 passengers+separate skipper cabin, combined with  a great hull design and generous sailplan. A real mile-eater with the power of the wind.  Read more

A top of the class commuter

1 available

Targa 25

A true legend in seaworthiness no matter the conditions. This is the support vessel to our sailboats that will take you safely and in full comfort from A to B if, when and where needed.