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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!

experiences

4.7

Premium

One way Aegina - Naxos sailing adventure on a big 50ft boat

Greece: Cyclades

6 days - 7 nights

One departure available

July

€1,100

Per person

4.9

A week in the flotilla in the Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,050

Per person

5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

July - October

Starting from

€990

Per person

Short trip around Paros and the small Cyclades

Greece: Cyclades

3 days - 3 nights

One departure available

August

€550

Per person

4.6

Cruise in the Dodecanese and off the coast of Turkey on a 17m boat with chef

Greece: Dodecanese

7 days - 7 nights

2 departures available

August

€1,600

Per person

4.9

One-way flotilla in the Ionian Sea from Lefkas to Zakynthos

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€1,150

€950

Per person

4.9

Kalymnos Paros via Astipalea e Santorini

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person - min 2 pax

Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

Starting from

€789

€710

Per person

4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

12 departures available

July - October

Starting from

€835

€752

Per person - min 2 pax

Classical Greece by sailing catamaran

Greece: Ionian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€1,300

Per person

5.0

Ionian Islands by Sailing: Trekking, Snorkeling and Sea Adventure

Greece: Ionian Islands

6 days - 6 nights

7 departures available

July - October

Starting from

€700

Per person

4.6

From Chios to Samos on my catamaran

Greece: North Egean Islands

6 days - 7 nights

One departure available

August

€980

Per person

Why book a holiday with Sailsquare?

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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

1776 reviews

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

07/7/2025

Diana U.

Italy

Amazing experience! It was my first time on a sailing boat, and it was incredible. We visited beautiful places and beaches. Ale and Carlo are the perfect duo to sail with! Ale is professional, knows everything about sailing and the best beaches, and was always available and super friendly. Carlo was also very kind and helpful. I'm a vegetarian, and he always made something special just for me. Thank you for an unforgettable week! Hope to come back soon! :)

From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

Italy

I 10 giorni in barca a vela sono stati bellissimi. Un’esperienza che mi ha riempito gli occhi e il cuore… non sarebbe stata tale se non avessi veleggiato in compagnia di bellissime persone con le quali si é creata una piacevole connessione. Ringrazio il “Super Skipper Andrea”, un professionista: competente, affidabile e generoso. Una vacanza che consiglio a chi ama il mare e la libertà!

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

07/7/2025

Maddalena D.

Italy

Una settimana bellissima, rigenerante e super positiva. Fabio e Irene ci hanno accolto su Àlisè e ci hanno fatto subito sentire a casa. La barca è bellissima, accogliente e spaziosa. Fabio è un ottimo skipper, molto disponibile e affidabile, mi sono sempre sentita al sicuro nonostante il maltemi non ci abbia mai mollato e a tratti è stato impegnativo. Irene è stata un’ottima co-skipper sia durante la navigazione che nella gestione dei pasti e della cambusa. Anche lei molto disponibile e attenta. Ottima esperienza. Grazie ancora

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

07/7/2025

Virginia B.

Italy

Vacanza bellissima, Andrea skipper preciso e simpaticissimo ci ha fatto scoprire posti meravigliosi e ci ha intrattenuti. Altra menzione d’onore a Marta che ci ha cibati e coccolati. Mattias vero lupo di mare! Mancate giá!

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