Sail Greece with an expert

Make the most of your sailing charter holidays in Greece

Sailing Holidays in Greece

Extraordinary team. Unforgettable experiences.

SailwithGeorge has been offering -carefully crafted- skippered sailing holidays in Greece since 2010, on a private or shared departure basis. Sailing in Greece, one of the finest sailing arenas in the planet, we provide unparalleled comfort aboard 56-ft or 51-ft sailing yachts and luxury catamarans.

Our heart-driven local crew delivers a highly personalized service, ensuring a full range of uncompromised sailing holidays in Greece that go beyond expectations.

Our main base is on Syros island in Cyclades and also depart from Paros, Mykonos, Santorini, Lavrio (close to Athens) and Corfu or Kefalonia in Ionian sea. Charter your sailing yacht or catamaran, starting from the heart of the action with direct access to fun from day one.

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Skippered Sailing beyond the expected

Hand picked local skippers

Our team of professional skippers is a big part of our success with a constant five star feedback since 2010. Heart-driven, with a positive mindset, friendly and approachable, with deep local knowledge and vast sailing experience you will always feel safe and relaxed with.

Meticulously prepared yachts

It is all about you feeling at home. Uncompromised comfort and safety on all our boats is a result of endless amount of love and care invested for upkeeping or preventive checks. And that applies to all six company-owned monohulls and the hand picked catamarans on which we operate.

Private & Shared Experiences

Others travel with family or friends as a private group wishing an entire boat for themselves and others are solo travelers, small groups of friends or couples that prefer to share it with like-minded people. Exploring ‘Ways to Sail’ with us and you will find your perfect match.

Direct access to fun

While you enjoy your extra night in Athens or a seafront lunch on one of the islands we work hard to get your boat ready and at the right place on the map. This means that you get to your first swim stop avoiding the crowds in busy marinas, waiting in boring places or long sailing hours.

One price for everything

We will always include all the costs related to the sailing experience in our quotation. So you will know from the start how much it will all cost. Without any hidden expenses or surprises you will be always sure that you stay in budget and for private groups it’s easy to share the bill.

Experience-rich routes

Offering the perfect blend between exploring, sailing, swimming, being active, just enjoying a beautiful dinner ashore or a drink on board requires local knowledge and experience. The stunning Greek islands is our back yard so you can be assured that you will get the most out of it.

Shared Sailing Experiences

Scheduled departures guaranteed to run. Ideal for solo travellers, couples and small group of friends.

Share & Sail

ex-Syros, Relaxing Sailing Holidays, 7 days

Join as a solo, couple or small group of friends and leave with many good friends. Swim, enjoy the Greek sun on deck, relax, taste the amazing local cuisine, explore the hidden gems of the Greek fishing villages

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Share & Sail

ex-Athens, Relaxing Sailing Holidays, 6 days

Designed for active explorers that appreciate peaceful moments. A perfect blend of water time and exploration ashore. Scheduled departures from March until November.

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Downwind Blast

A One-way Cycladic Adventure, Lavrio to Santorini 10 days

Embark on an exhilarating one-way sailing adventure from Athens to Santorini. This carefully designed downwind route takes full advantage of the prevailing north-to-south winds of the Greek summer, ensuring an exciting, wind-powered journey across the Aegean.

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Private Sailing Experiences

Exclusive departures for your private group. Ideal for families or larger group of friends (4 persons or more)

Catamaran Week

Catamaran Sailing beyond the expected ex-Lavrio or ex-Paros

The luxury Catamaran sailing week in Greece, downwind Lavrio to Paros or circular Paros to Paros is a high-end experience beyond expectations that clearly exceeds the standards of the charter market. Ideal for private groups of 4-11 persons who appreciate the extra space, the extra service and would like to sail Greece in their own pace and in an uncompromised way.

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Family Week

Happy kids, Happy parents, ex-Paros

The Absolute Family Adventures are private departures, tailor-made to be ideal to families with young yachties, of any age. Apart from sailors we are also parents ourselves so we know what it takes for an unforgettable family holiday that everyone in the family will truly equally enjoy. Our approachable skippers, our family-friendly route and the optional activities onboard or on land always do the trick.

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Tailor-made Experiences

Any route & duration handcrafted by SailwithGeorge

Private departures with maximum flexibility (in route, duration and boat type) that will match any private group of friends or family and any back to back travel arrangement. Ideal for private groups of 4-11 persons

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