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Yacht sailing holidays & skippered tours in Italy

Discover more than 2 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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 - Yacht sailing holidays & skippered tours in Italy

12522 reviews

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Short sailing cruise in the Gulf of Naples

07/11/2025

Daniela D.

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Italy

My first experience on a sailing boat was an unforgettable experience, when the Universe puts the right people on your path at the right time. Every moment was intense, perfect and unforgettable, despite the rough sea, the change of tour due to the wind and the sea was all organized and managed calmly and with great professionalism and safety by Alessandro who was our skipper. Thank you for these three unforgettable days where we shared beautiful moments and the magic of being perfect strangers but immediately all old friends. A sensation never experienced. A gift like the breeze, the sun, the sea and the sense of touching freedom and embracing it totally.
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Life-changing experiences - Escape to the Pontine Islands

07/11/2025

Emanuela P.

First experience on a sailboat, fantastic!!!!!! perfect organization, our skipper Francesco attentive and professional,,made me feel safe at all times.,Thank you for everything
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Sailing weekend in the Pontine Islands

07/10/2025

Stefano M.

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Italy

Beautiful boat trip. I discovered two pearls: lucky those who can reach the Pontine islands habitually. Roberto is a unique skipper. Clearly an expert with many hours of navigation behind him: he knows how to command, manage the boat, put you at ease. Give great tips for living the best on the boat and on land. Excellent cook: he prepares delicious dishes and aperitifs, which make the trip more than pleasant. [hidden] is a super boat!!!! Excellent travel companions met. A real holiday. The head was freed to fully experience all the beauty that was around us. Thank you Roberto.
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Dream sailing on a fully-equipped catamaran

07/9/2025

Alessandro B.

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Italy

For us it was the first experience on a boat and all expectations were met! The most exciting part was being able to sail with [hidden]. The boat is in very good condition and the crew we met was top. We will certainly repeat the experience in the future.

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