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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

8 departures available

April - July

Starting from

€360

Per person

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4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

19 departures available

May - October

Starting from

€640

€576

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€1,020

€918

Per person

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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

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4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

May - July

Starting from

€350

Per person

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4.8

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

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - September

Starting from

€600

€540

Per person

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4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

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4.8

Super!

Discovering the wild Peloponnese

Greece: Peloponnese

7 days - 7 nights

One departure available

July

€880

Per person

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4.8

Super!

Route to the South: The Small Cyclades and spectacular Santorini

Greece: Cyclades

7 days - 7 nights

One departure available

September

€850

€765

Per person

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5.0

Super!

Sailing in the Aegean, the sea of the Gods!

Greece: Cyclades

7 days - 7 nights

One departure available

May

€500

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 - Sailboat holidays & skippered tours

17631 reviews

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Weekend among the most beautiful coves of Elba

04/21/2026

SARA N.

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Italy

Unforgettable sailing experience with Marco and Carmen! 🌊⛵ From the first moment we felt welcomed as friends: professional, helpful and always attentive to every detail. The weekend was well organized, with breathtaking views, moments of relaxation, aperitifs and lots of laughter. We sailed to the island of Elba, saw dolphins and caught some excellent fish that we then cooked and ate together. All wonderful! Marco is an experienced skipper who conveys safety and passion for the sea, while Carmen adds a special touch with her kindness, sympathy and care for guests. I recommend this experience to anyone who wants to experience the sea in an authentic and relaxing way. Definitely to be redone, we will see each other 😜 again
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Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Goutham B.

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Germany

I had a wonderful week of sailing with this team. Skipper is super cool and I enjoyed his company a lot. He was happy to customize the sailing plan according to each of our requirements and was friendly to even cook for us a few times (The pasta was delicious). Bertrand even allowed me to stay on the boat for few extra days at Aegina. However, for my bad luck, an unfriendly couple was part of the crew and they were neither willing to pay for the skipper's food, nor willing to cook which was clearly mentioned in the advertisement as the responsibility of the whole crew. Even then the skipper was cool enough to invite us all to dinner in order to build up a family feeling between the crew members. Despite all this effort, It's unfortunate to see them giving a bad review about their sailing experience here. But other than this, personally I enjoyed the whole sailing week with Bertrand and his team. I am looking forward to sail with your team in the future.
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Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Thomas S.

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United Kingdom

The captain (Alex) asked us to lie to the police as soon as we got there about being his friends and not chartering this boat. Something about not having a charter lisence, which made us feel very uncomfortable, even though Bertrand now denys it. The toilets stank and the shower was very uncomfortable to use, but I guess thats just how boats are. It leaked when it rained and it is fairly cramped, and we left asking why we paid that price for that boat. We didn't feel like we got value for our money at all and the organiser was very rude to us when we brought up our concerns. At least the islands were nice.
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Easter in Capraia and Corsica

04/14/2026

Giunio M.

-

Italy

Wonderful days in the company of quiet people and lovers of the sea and sailing

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