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Yacht sailing holidays & skippered tours in Greece

Discover more than 12 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

12

experiences

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Autumn Gems of Cyclades away from the crowds on 51 ft yacht

Duration:

7 days - 7 nights

Greece:

Cyclades

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2 travellers

have left

Starting from

€319

€580

Per person

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4.8

South of Lefkas, unspoiled nature, bays of Meganisi and myths of Ithaca

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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58 travellers

have left

€495

€550

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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60 travellers

have left

Starting from

€523

€550

Per person

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5.0

Educational sailing cruise to the Ionian Islands from Lefkada

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€1,235

€1,300

Per person

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4.4

Catamaran in the sea of Ulysses - All inclusive

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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19 travellers

have left

€1,250

Per person

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5.0

The sailing adventure of your summer - Steward on board

Duration:

7 days - 6 nights

Greece:

Dodecanese

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4 travellers

have left

€1,450

Per person

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7 Day Greek Sailing Adventure - Dodecanese Islands - All inclusive

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,653

Per person

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5.0

Super!

Sailing in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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156 travellers

have left

€1,020

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic, the best local experience

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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15 travellers

have left

Starting from

€1,600

Per person

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4.7

Premium

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

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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76 travellers

have left

€890

Per person

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Antiparos Discovery Schooner Tour - Despotiko - Blue Lagoon

Duration:

1 day - 0 nights

Greece:

Cyclades

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2 travellers

have left

€130

Per person

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Sporades Islands: sailing holidays are more than just holidays!

Duration:

7 days - 7 nights

Greece:

Sporades

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2 travellers

have left

Starting from

€800

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

1726 reviews

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The fantastic Saronic Islands and the surroundings of Athens

10/17/2024

liz b.

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United States

This was a long time ambition of mine and Alessandro delivered an incredible experience! It was truly relaxing, very little to think about beyond where to eat when we went to port. Our schedule was flexible based on our mood, and fortunately the weather was cooperative.
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The fantastic Saronic Islands and the surroundings of Athens

10/17/2024

anna a.

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Italy

Avvertenze: può dare dipendenza.
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Big and luxurious 60ft catamaran in Saronic - best local experience

10/15/2024

Kiki Kiersten G.

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United States

If you need a sign to take the most relaxing and thoughtful sailing vacation you’ve ever dreamed of, this is it! You must have Greg and Aga take you sailing around the Mediterranean! In between sailing and enjoying incredible meals prepared by Aga, there is plenty of time for naps in the sun, snorkeling, paddleboarding, board games, cliff jumping, wine tasting, reading, and relaxing. Greg even went above and beyond to accommodate my husband’s kiteboarding from the boat. If you have special requests or needs, they are eager to tailor your vacation to you! You can be as involved in the sailing as you wish. Aga’s meals deserve another shout-out! We were so happy with the healthy and exquisite vegetarian meals, and I was always excited to see what she would create next. She is very creative and takes great care in sourcing local products from the villages, vineyards, and farmers she connects with on her travels. Greg and Aga have spent years sailing around the Greek islands and have found special, off-the-beaten-path harbors, villages, and taverns. They have fostered relationships with locals on each island, and as a guest, you get to enjoy the fruits of their efforts. We spent an evening with a local family at their winery and enjoyed a beautifully prepared meal with wine pairings. Each night at the tavernas, Aga’s recommendations were incredible. Sometimes the seafood was so fresh that they cleaned the fish right after you ordered it! The Zorba Cat catamaran is spacious, beautiful, and incredibly comfortable. Each cabin had its own bathroom! Even with multiple parties on our trip,
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The alternative to the catamaran in the Ionian Islands

10/15/2024

Belinda B.

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Australia

Best live aboard sailing trip I have done. The boat was exceptionally comfortable and everything clean and in ship shape ! The skipper was great at helping us learn the ropes to participate in the sailing if we wanted to. I loved having the SUP and snorkel sets on board to use when we moored in beautiful bays. It was terrific to catch fresh fish to eat along the way too. Thanks so much to Manuele for making my first trip to Greek Is such a wonderful experience.

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