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Private yacht sailing holidays with skipper in Greece

Greece is one of the best sailing holiday destinations in the world! Over 16,000 km of beautiful coastline offers countless exciting itineraries. A whole boat reservation allows groups of family or friends the freedom to - with your skipper - craft a personalised holiday with activities and routes that tailored to your specific holiday style and wishes.

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€1,300

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

3 departures available

October

€570

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€570

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

Starting from

€950

€570

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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4.5

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€890

Per person

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4.2

Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

2 departures available

October

Starting from

€829

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

Per person

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4.7

Luxury catamaran cruises in the Greek islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

October - November

€1,000

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

September - November

Starting from

€700

€665

Per person

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4.2

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

Why book a holiday with Sailsquare?

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Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Private yacht sailing holidays with skipper in Greece

481 reviews

Corfu between bays, taverns and myths.

09/26/2026

Kevin E.

-

US

What a great week. Boat was perfect. Captain / crew were spot on. The friends we made sharing the boat were incredible. Itinerary was just right.
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Corfù Paxos Antipaxos

09/26/2026

Mirella S.

We had an incredible week sailing around Corfu, Paxos, and Antipaxos with Giovanni and Stefania, and we couldn’t recommend this experience more. From the very first moment, the crew made us feel completely comfortable, safe, and taken care of. They were attentive to every little detail while also making everything feel effortless and relaxed. Over the course of the week, they went from being our crew to feeling like a second family. It was the perfect combination of beautiful destinations, unforgettable days at sea, lots of laughs, and so many special moments that we know we’ll remember forever. Everything was absolutely perfect from beginning to end. Giovanni and Stefi, thank you for giving us such an incredible week and memories that will stay with us forever. We’re already thinking about where our next adventure with you will be! ❤️⛵️
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Luxury catamaran cruise in the Cyclades

09/25/2026

Anne-Sophie T.

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GB

We had an amazing time on this catamaran cruise! Originally we were booked to sail to the Cyclades, but the weather didn't cooperate, so the itinerary switched to the Saronic Islands instead. Honestly, it turned out to be a fantastic backup plan — the islands were stunning and we didn't feel like we missed out at all. Bertrand, our skipper, made the whole trip. He was friendly, easygoing, and so accommodating with the change in plans, and he clearly knew the area well because he took us to some incredible spots we wouldn't have found on our own. He made sure everyone was comfortable and having a good time throughout the trip. Even with the last-minute change of course, this ended up being one of the highlights of our vacation. Highly recommend it if you're looking for a relaxed, well-run sailing trip around the Greek islands!

Sailing course in the Cyclades

09/24/2026

ruggero r.

-

IT

Amazing experience!! The skipper followed me step by step, teaching me the basics of sailing with great professionalism and patience. We sailed with a perfect wind to have fun and learn and the nights spent in the roadstead were all in coves of fantastic islets. Highly recommended.

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6 reasons to choose a whole boat reservation in Greece for your next sailing holidays:

  • Experience the beauty of one of the world’s best sailing destinations.
  • Explore your choice of the thousands of Greek islands.
  • Find holidays throughout the Ionian islands, the Cyclades, the Dodecanese, the Saronic islands and the Athens area.
  • Travel with maximum freedom, working with your skipper to construct a holiday perfect for your friends and family.
  • Discover Greece at your pace.
  • Embrace quality family or friend time with an original holiday and create unforgettable holiday memories.

Travelling in Greece in a whole boat with a skipper

What a whole boat sailing holiday offers

Sailing holidays are a brilliant opportunity for groups of family and friends to come together and create special holiday memories. Booking a whole boat allows you some luxuries you may not find when sharing the boat with travellers. One particular luxury that could make a great different to your holiday structure is the freedom of your itinerary - which may be especially relevant when travelling in Greece where there is such an abundance of special islands and destinations to visit. Reserving a whole boat then allows you to work with your skipper to tweak and tune the holiday to suit you and your friends and family.

Locations in Greece for a whole boat sailing holiday

Across the Ionian islands, the Cyclades, the Dodecanese, the Saronic islands and the Athens area you can find holiday listings with whole boat booking availability. If you come across an experience either isn’t or doesn't explicitly appear as a whole boat listing, you can reach out to the organising skipper through the “contact the skipper” button present on each holiday listing to understand their upcoming availability.

Tips to help you to better plan for your next sailing holidays in Greece:

All you need to know about your next cruise in Greece aboard a sailboat.

When to go to Greece for a sailing holiday & how long should I visit?

The Greek climate is pleasant and generally suitable for sailing holidays throughout the year. Travellers might want to consider a sailing holiday in Greece during the slightly quieter months of May, June, September, or October when weather conditions are still generally warm. Depending on the style of sailing experience you are looking for, each group of islands has their unique personality, and each island it’s special charm. Travelling with a local, experienced skipper means that you are able to travel to the popular destinations as well as lesser known spots, tucked away from mainstream tourism. Again, depending on the set of islands you are visiting, the recommended duration will differ. We recommend a minimum of two weeks to discover the Cyclades and the Dodecanese. If you have less time, we recommend looking at holidays in the Ionian, Saronic, Sporades and Crete.

Transport options to and from your holiday in Greece & sailing with a family

Greece is home to a number of international airports, including Athens, Corfu, Kos, and Kefalonia. Prices will vary substantially depending on the month, you may find cheaper alternatives in the months before and after the peak months of July and August. There is a highly developed network of ferries that are a main form of transport, and maybe necessary to reach your skipper. Your skipper will be best placed to give you advice on transport options according to the specific embarkment, disembarkment and season of travel. Greece is a location that is particularly family sailing holiday friendly, this as there is generally a warm climate, plenty of mooring options, and many facilities for activities such as water sports.

Greece: the best travel ideas

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