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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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4.7

COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

Italy: Sicily

4 days - 3 nights

2 departures available

September

Starting from

€390

€351

Per person

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4.8

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

63 departures available

January - December

Starting from

€200

€180

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

September - October

Starting from

€220

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

September - October

€850

Per person

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4.9

Super!

Traveling and dreaming in the Gulf of Poets - All Inclusive

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

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4.8

Super!

Introductory sailing course

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

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4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

October - November

€299

Per person

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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands with photographer on board

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€370

€352

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

One departure available

October

€550

Per person

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4.8

Super!

EGADI AND COUSCOUS FEST of San Vito Lo Capo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

€570

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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5.0

Super!

From the Fiji Islands to New Zealand: a unique adventure

Pacific Ocean: Fiji Islands

12 days - 12 nights

One departure available

September - October

€1,500

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

17477 reviews

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

09/17/2025

Mauro Z.

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Italy

Very nice cruise, despite the weather was not favorable, the skipper managed to let us enjoy the beauties of the Costa Smeralda
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Weekend at the Pontine aboard a splendid 16-meter sailboat

09/17/2025

Giulia E.

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Italy

It was my first time on a sailing boat but the skipper Leonardo and his wife Elena were immediately very professional and attentive to everyone's needs. The boat is very nice, functional and clean; perfect for enjoying the sea in total relaxation. The excellent company, the favorable weather and the crystal clear water of the Pontine islands then made the experience perfect!
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Egadi paradise for sailing and snorkeling

09/17/2025

Vicky H.

-

Belgium

Mario is a competent and friendly skipper. The Egadi islands are beautiful and the boat is in good shape. It is a pity that 2 French-speaking fellow passengers had a lot of criticism, made little effort to involve the skipper in the conversations and were very present during the trip, to the displeasure of the other passengers.
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A week in the Aeolian Islands - 6 islands in seven days

09/17/2025

Giuseppe I.

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Italy

The sailing trip with Nicola was an experience that enriched me a lot, unique emotions and sensations. The navigation, the wind, the sun and the sea created a perfect mix of adventure and relaxation. I recommend everyone to try this experience at least once in their life: it is an opportunity to discover the beauty of the sea, the Aeolian Islands and the feeling of freedom. Thanks to all the crew, who made all this possible.

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