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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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4.2

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

20 departures available

May - October

Starting from

€780

Per person

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4.8

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€962

€866

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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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

June - October

Starting from

€690

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

€290

Per person

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5.0

Istria and Kvarner sailing – Relaxation and comfort with hostess on board

Croatia: Istrian peninsula

7 days - 7 nights

5 departures available

May - June

€1,100

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

October

€600

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

5 departures available

July - August

Starting from

€750

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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4.2

Discover the South of Sardinia by sailing, white beaches and tradition

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

August

Starting from

€896

€806

Per person

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4.6

Enjoy: in the blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

18 departures available

May - September

Starting from

€600

€540

Per person

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

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

19287 reviews

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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

Francesca A.

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IT

We spent a beautiful week together with Alessandro.Even if the weather was not the most clement, we were able to visit beautiful and characteristic places that we could never have discovered in any other way. In addition to the fantastic experience itself, it was Alessandro who made the difference: an experienced captain, a true master of life, with a wealth of stories to write a book about. We spent days between the sea, the wind and its stories, eating and drinking together as old friends. Thank you Ale, we will always carry you in our hearts with the hope of meeting again soon. Francesca and Davide

Squid Regatta

10/20/2026

Valentina M.

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IT

Wonderful weekend with participation in the squid regatta that allowed us to appreciate Francesco's skills as a captain. It was fun to get involved in conducting! [hidden] is a gem of a boat: convenient spaces, clean and comfortable.
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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

manuela c.

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IT

I had a great time on the boat with Ale, a professional, kind, helpful person who tried to please everyone (and it's not easy!) and super nice. I saw very beautiful places despite the islands being quite man-made, took nice baths in magnificent roadsteads and visited beautiful villages with even some trekking. Beautiful, solid and comfortable, the boat, suitable for any navigation, I have always felt safe. Ale also always available to cook for everyone! Experience to be done again next year in other islands. Thank you
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It's time for sun and sea!

10/19/2026

Francesco G.

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IT

A special thanks goes to Carlo, exceptional owner and skipper, super welcoming, prepared and smart. He managed to make us feel immediately at ease by transmitting his passion for the sea and guaranteeing us a stay in total relaxation and safety. Very nice, comfortable and clean boat. Highly recommended experience for anyone who wants to unplug and experience the sea in an authentic way.

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