header cover
logo

Log in

Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

cover image
avatar image

4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

July - August

Starting from

€1,450

Per person

cover image
avatar image

4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

cover image
avatar image

4.9

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

cover image
avatar image

5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

cover image
avatar image

5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

cover image
avatar image

4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

June - September

Starting from

€1,080

Per person

cover image
avatar image

4.9

Super!

From Samos to Kos Dodecanese North on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

cover image
avatar image

4.9

Super!

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

cover image
avatar image

5.0

Super!

10-Day Cruise to the Sporades & Nature Park

Greece: Sporades

10 days - 10 nights

One departure available

August

€1,250

Per person

cover image
avatar image

5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

cover image
avatar image

4.8

Super!

Luxury catamaran cruises in the Greek islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

12 departures available

June - November

Starting from

€1,000

Per person

cover image
avatar image

5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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

Reviews - Yacht sailing holidays & skippered tours in Greece

1924 reviews

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

06/22/2026

Michela B.

-

IT

A beautiful experience shared with unknown but amiable and sociable people. We were lucky. Gianfranco, the skipper is very good and this makes navigation safe and relaxed. The Sporades are beautiful, very green and with a crystal clear sea. Super recommended.
avatar image

Catamaran with chef in the magical sea of the Ionian Islands

06/21/2026

Lorenzo G.

-

GB

We had an amazing catamaran holiday in Greece. The places we visited were absolutely stunning, with crystal-clear waters, beautiful beaches, and unforgettable scenery. The catamaran was fantastic, comfortable, well-maintained, and perfect for exploring the Greek islands. A special thank you to our skipper and hostess, who made the entire experience exceptional. Their professionalism, kindness, and attention to detail created a relaxed and enjoyable atmosphere throughout the trip. The food was delicious, and every meal was prepared with great care. Another highlight was sharing this adventure with such a wonderful international group of fellow travellers. It was a pleasure meeting people from different countries and creating great memories together. Thank you to our skipper and hostess for the excellent sailing, the wonderful cuisine, and for making this such a memorable holiday. We would highly recommend this experience and would gladly do it again.

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

06/16/2026

Liubov S.

A wonderful experience! Highly recommended!
avatar image

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

06/16/2026

Tomas F.

-

GB

No No No !!!! :(. I want more. This 7 days with Allesandro ( Skipper) and Carlo (Host) was Amazing. They will take you to the best places around Corfu. Paxos and Antipaxos are paradise. Fantastic food during sailing, healthy and everyday different. We even catch big fish during sailing, and next day bee served for lunch by Fantastic Carlo. I could write review for 100 pages, but you have to explore this wonderful trip. Greetings also for Chiara, Catarina and Luca.

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964