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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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4.8

Super!

Flottiglia Sun & Fun Marmaglia - Età 25-40 anni

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,100

€950

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€719

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€900

Per person

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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

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4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€690

€621

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€751

Per person

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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

One departure available

August - September

€660

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€583

€525

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

€293

€264

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

16234 reviews

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Egadi Islands & San Vito Lo Capo - Blue Transparency!

07/14/2025

TATIANA CRISTIANA D.

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Italy

Francesco is a highly qualified skipper who has a great command in driving the sailboat, in doing all the necessary maneuvers with great promptness and safety. Sailing with him is a certainty, absolutely recommended.
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Week between the Tuscan Islands and North Corsica

07/14/2025

Flavia G.

-

Italy

Francesco is an experienced skipper, skilled in managing the unexpected and meeting the needs of the whole crew. The boat is comfortable and equipped with everything you need to spend a pleasant holiday.
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

07/14/2025

Francesca N.

-

Italy

Excellent experience, the [hidden] is a spacious and very well maintained boat, updated with many small features that make it very comfortable. Captain Luca immediately showed that he knows his boat and the area in which he sails like the back of his hand and has earned everyone's trust from the beginning, even when the weather was not favorable, always making us part of his decisions. Tommaso, despite being very young, was a constant support, always very kind and attentive to everyone's needs, but also very nice and always ready for a joke. Above all, he is an excellent cook and together with Luca he spoiled us all week with excellent aperitifs, lunches and dinners. As for the area, I think it needs no introduction, the sea is crazy and the islands one more beautiful than the other. Ultimately a holiday to be repeated!
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Discovering the Aeolian Islands Between Nature, Relaxation and Fun

07/14/2025

davide p.

-

Italy

Excellent from all points of view. Superlative skipper

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