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Sailboat yacht sailing holidays & tours in Greece

Discover more than 49 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

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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

4 departures available

August - October

Starting from

€550

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

€1,080

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

3 departures available

August - October

Starting from

€550

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - November

Starting from

€650

€618

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

September

€750

Per person

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5.0

Super!

From Paros to Milos, the hidden gems of Cyclades

Greece: Cyclades

5 days - 5 nights

3 departures available

August - September

Starting from

€900

€810

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

€790

Per person

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4.8

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

Per person

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5.0

Super!

We will depart from Kos to head to Mykonos with a very comfortable boat

Greece: Cyclades

7 days - 6 nights

One departure available

September

€750

Per person

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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 - Sailboat yacht sailing holidays & tours in Greece

1702 reviews

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Come and discover the Saronic Islands from Poros

08/19/2025

Yigit Emre C.

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Netherlands

Due to a last minute change of plans, we could not join this sailing trip ourselves. Instead, our close friends went, and since we fully trust their judgment, we are sharing their experience here with their words. This was, without a doubt, the worst sailing trip we have ever experienced. The couple running the boat were friendly on the surface, but they are far from professional and not suited for this kind of business. For so many reasons, we would never recommend this trip: • Food & Timing: We were charged €25 per person per day for meals, but the quality and timing were terrible. On the first day, dinner was served at 10:30 PM, even though everyone had just arrived tired from traveling with no consistency or planning. Lunches were served at completely random times, sometimes at 3 PM, sometimes at 1 PM. • Dietary Needs Ignored: No one asked about dietary restrictions or allergies in advance. When we mentioned we don’t eat pork, dinner that day turned out to be pork. Instead of preparing something else (they had all day to buy something else), the captain caught three tiny fish and said, “This is your dinner.” It was not nearly enough, so after asking, they got plain pasta with half an eggplant. We paid the same as everyone else who ate pork. • Hygiene & Water: The drinking water container had algae at the bottom. Dishes were washed with seawater, so everything tasted salty. The kitchen and utensils were far from clean, and the boat itself was messy. • Random Schedule: Everything was done according to the crew’s convenience, not the guests’. Even when we needed rest or had an early ferry, we had to wait until the couple finished eating or drinking with their friends. • Route & Stops: On 3th day, we sailed for 4.5 hours straight, passing beautiful islands full of boats, only to stop at a place with nothing and it was 7pm when we arrived so we couldn’t do anything there. The next day, we sailed 3 hours just to get back to Poros. • Docking Issues & Extra Costs: When returning to Poros, Sabine and Patrick refused to dock at the marina, even though they had picked us up from there earlier. Later they admitted they didn’t want to pay the €17 docking fee. Because of this, both us and other couple had to take separate taxis to get to town, and over the course of the trip we ended up taking three taxi rides (€25 total) just to reach town and ferries. It wasn’t the money itself but the unprofessionalism, they should have dropped guests back where they picked us up. • Alcohol & Safety Concerns: On the last night, instead of returning us to the boat early so we could pack and rest for a morning ferry, the crew spent hours drinking with their group of friends. We had to wait until midnight to return. By then, both the Sabine and Patrick and their group were heavily drunk, barely able to stand. Still, six people were taken on a zodiac back to the boat in dangerous conditions. After dropping us off, the crew went back to continue partying with their friends. At the end of the trip, when asked for feedback, we explained all of these issues. The response was, “But you never told us you don’t eat pork.” Our answer was simple: “You never asked.” On the very last day, when we were finally alone with the other couple who traveled with us, they also shared their experience. Since both they and the crew were French, they mostly spoke among themselves during the trip and everything seemed fine from the outside. But once we spoke privately, they admitted they were just as unhappy as we were nothing met their expectations and they had the same complaints. Unfortunately, because they booked this trip through a friend, they cannot leave a review here. In summary: The food, hygiene, comfort, route planning, and professionalism were all a complete failure. While the couple may seem nice, they should absolutely not be running this as a business. It felt like they were sailing for their own pleasure, while guests had paid good money to tag along as an afterthought. More than €1,000 was wasted, along with time and energy. Absolutely not recommended.
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Sailing from Corfu to Zakynthos in 7 days

08/19/2025

Paolo R.

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Italy

Max was not just a captain or a skipper, he was a great and highly appreciated travel companion. His competence and tranquility meant that even small moments of unforeseen events during navigation were handled in the most perfect and professional way possible. Great chef, always ready and always available to welcome proposals and requests from the crew. A 5-star experience definitely to be repeated, surrounded by the unexpected and exciting encounter with seals. To the next wind
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Small Cyclades

08/18/2025

Franesco B.

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Italy

An exceptional holiday! Challenging sea conditions but two professionals proceeded impeccably. Together we sailed sublimely, overcoming adversity, finding ourselves immersed in a true and uncontaminated reality. Undoubtedly a recommendable holiday but I always suggest doing it with the mentality of those who want to help a companion (not a skipper), of those who want to savor intense and sincere realities forgetting some secondary comforts. Finally, special mention to the culinary skills of Lorenzo and Annalisa. Super
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Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

08/17/2025

Vincenzo P.

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Italy

Arthur Excellent Skipper, always ready to solve unforeseen events that are never lacking on the boat, connoisseur of all the most beautiful coves and places on land to visit. During the days there are several stops in various places making every day never boring. PLUS evening group games on the boat.

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