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!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - October

€750

€713

Per person

cover image
avatar image

4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

7 departures available

August - October

€600

Per person

cover image
avatar image

4.9

Super!

Cyclades from Paros to Milos on magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

cover image
avatar image

4.8

Super!

Croisières en catamaran de luxe dans les îles grecques

Greece: Saronic Islands and Athens area

7 days - 7 nights

17 departures available

June - November

Starting from

€1,000

Per person

cover image
avatar image
Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

5 departures available

July - October

Starting from

€779

€701

Per person

cover image
avatar image

4.9

Super!

The North Dodecanese from Samos on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

June - July

€1,000

Per person - min 2 pax

cover image
avatar image

4.9

Super!

From Milos to Zakynthos: the Peloponnese on a magnificent 15-meter boat

Greece: Peloponnese

10 days - 10 nights

One departure available

September

€900

Per person - min 2 pax

cover image
avatar image

4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

cover image
avatar image

5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

3 departures available

June - October

Starting from

€950

€760

Per person

cover image
avatar image

4.8

Super!

Catamaran with Chef in the magical sea of the Ionian Islands - Holiday for SINGLES

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,450

Per person

cover image
avatar image

4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

18 departures available

June - November

Starting from

€1,000

Per person

cover image
avatar image

4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

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

1914 reviews

Cast off for a week at sea, a thousand ways to experience it!

06/2/2026

Fabienne H.

-

BE

An unforgettable week on a sailboat! It was my very first sailing experience and I couldn't have asked for anything better. From the beginning, Alex, our skipper, has listened to our desires, expectations and needs, while adapting to our pace. Her enthusiasm, sense of adventure and good humour made this week particularly enjoyable. He knows how to share his passion with simplicity: we even had the opportunity to learn some navigation techniques and participate in the maneuvers, which made the experience even more fun. Sailing with the wind provides an incredible feeling of freedom, far from everyday life. Between the beautiful landscapes, the moments of relaxation and the small adventures at sea, each day was unique. I leave with a head full of memories and the desire to do it again. I recommend this experience 100% to anyone who dreams of discovering sailing, whether for the first time or for sailing enthusiasts. Roxane

Sailing in the Aegean, the sea of the Gods!

06/1/2026

Viviana C.

A tour full of adventure! Andrea is very professional and with his experience he made us discover these wonderful islands, in all their beauty.

Sailing in the Aegean, the sea of the Gods!

05/31/2026

James W.

-

IT

Everything about this experience was 5 star! Andrea is an incredible professional who knows how to curate the perfect tour. If given the chance, we would absolutely sail with him again!
avatar image

Sailing in the Aegean, the sea of the Gods!

05/25/2026

Massimo O.

-

IT

Andrea is exquisite and knows how to put you at ease. He is prepared and able to solve the various unforeseen events typical of life at sea. The variable weather prevented us from making the most of the experience at sea but the alternative proposals for shore excursions proposed by Andrea were equally exhaustive.

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