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All inclusive yacht sailing holidays & tours in Italy

Discover more than 7 opportunities to get on board a All inclusive adventure in Italy. 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 - All inclusive yacht sailing holidays & tours in Italy

553 reviews

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A day sailing in the fantastic Gulf of Trieste

10/20/2025

Monica C.

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Italy

The skipper Paolo simply fabulous. The super cozy and high-performance boat. We had a beautiful, immersive experience and learned even a minimum basis of sailing concepts
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A wonderful day.... on Lake Garda - ALL INCLUSIVE

09/30/2025

MARIA GRAZIA P.

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Italy

A wonderful sailing experience! 🚤⛵️ We spent Sunday in the company of nice people, with impeccable organization. Emanuele proved to be an exemplary professional: availability, kindness and attention to detail made us feel immediately at ease. Great food, stunning views and a relaxing atmosphere that made the experience truly unforgettable. Everything perfect: absolutely to try and recommend!
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Traveling and dreaming in the Gulf of Poets - All Inclusive

09/23/2025

Marta D.

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Italy

The boat is comfortable (especially the bed!!) and in excellent condition The service is all inclusive, so on the one hand it is practical on the other hand it is not certain that you will find what you would like They were very kind to buy gluten-free pasta for me who is celiac A shame not to sleep in the roadstead and the sea points were not always wow, but it is a nice experience that I would repeat!
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Traveling and dreaming in the Gulf of Poets - All Inclusive

09/23/2025

Luca P.

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Italy

Fantastic weekend with Giorgio and Francesca who made us feel like special guests all the time

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