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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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4.0

European Offshore Mile Builder - Leg 5: St Tropez to Malta

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€550

Per person

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5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

3 departures available

September - October

€950

Per person

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AMERICA'S CUP in pursuit of the AC40s!

Italy: Naples & Amalfi Coast

1 day - 0 nights

4 departures available

September

€180

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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4.5

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€290

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

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4.5

Weekend on a sailing boat in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€380

€350

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

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 - Sailboat holidays & skippered tours

19187 reviews

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Egadi paradise for sailing and snorkeling

09/22/2026

Roberto P.

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IT

We spent a week in the Egadi Islands in September 2026, and it was a positive experience from every point of view. Mario is not only a skipper with a lot of experience, but also and above all an exceptional person. Always attentive, helpful, and of a truly exemplary calm and kindness. Thanks to the favorable wind we were able to make beautiful sails between the islands and the beautiful sea of the Egadi. We have seen many bays and coves and Mario has always been prepared to suggest the best places to visit (both at sea and on land) and the experiences not to be missed (sunrises and sunsets are not to be missed). He made us visit many places, one more beautiful than the other, and we collected so many memories, that the holiday seemed much longer than 7 days! Also on Gaia, his assistant and hostess, it is only right to spend excellent words for professionalism, availability and sympathy. The hostess service on board is one of those gems that we did not know we needed, and Gaia with her manners, her warmth and her professionalism, has given added value to this service. A real pleasure to be on board in the company of both. Two truly exceptional travel companions, who joined the other equally exceptional guests, with whom we immediately bonded, thanks to our common love for the sea. As for the boat, it is equipped with all comforts. Large and comfortable cockpit. Spacious and comfortable dinette. Reserved bathrooms in the individual cabins with electric toilet. The hammock, and also a watermaker. It is impeccably maintained, and was our home for 7 beautiful days. We couldn't have asked for anything better. Thank you very much for giving us an unforgettable week. We plan to contact Mario again for other experiences together, hoping to have Gaia's company again, and we would like to recommend Mario without any doubt. The only negative thing is not being able to put 10 stars, because 5 is absolutely not enough

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

09/22/2026

Birgit H.

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DE

What a great trip! Seen a lot! Ate a lot! Beautiful coves where you can anchor and admire the sunset with an aperitivo. Bledar is a very responsible skipper, very helpful and always attentive to the wishes of his guests. He makes several suggestions every day and knows the most beautiful corners. And his cooking skills are excellent too! It's just a pity that there was too little wind to sail!

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

09/22/2026

MARGHERITA D.

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IT

Unforgettable sailing week! Impeccable organization from the first contact, everything perfect down to the smallest detail. Spotless and super comfortable boat. Special praise to our skipper Alexander: in addition to being a serious professional, highly trained and always attentive to safety, he turned out to be an exceptional cook! Alexander is attentive to the needs of his passengers, showing a lot of availability. Its simplicity allows you to be at ease for those who want a human but at the same time professional relationship. Sharing small naval activities makes the experience really interesting for those approaching the boat stay for the first time. Experience to be redone 100%, highly recommended

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/22/2026

Francesca F.

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IT

A simply fantastic week! We sailed between the Maddalena archipelago and the Costa Smeralda, visiting wonderful places and dreamy coves, but the most beautiful thing was experiencing the sea from the boat: waking up every day in a different place, swimming in incredible waters, sailing with the wind and enjoying spectacular sunsets. A special note goes to the skipper, always available and very competent; We appreciated his desire to sail and turn off the engine whenever conditions allowed, making us really live the experience of sailing and not simply a boat holiday. In short, one of those holidays that when they end you think: "Do we really have to go home?" Super recommended! And I... I would already be ready to start again!

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