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Yacht sailing holidays & skippered tours in Italy

Discover more than 19 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

May - June

Starting from

€600

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

May - June

Starting from

€689

Per person

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4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

4 departures available

May - June

Starting from

€950

Per person

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4.7

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

May

Starting from

€200

€180

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

One departure available

May

Starting from

€430

€409

Per person

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4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

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4.8

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

5 departures available

May

Starting from

€210

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

4 departures available

May

Starting from

€250

Per person

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Sardinia Race... tour of Sardinia in a squadron... NoStop!

Italy: Southern Sardinia

5 days - 4 nights

One departure available

May - June

€800

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

5 departures available

May - June

Starting from

€1,320

€1,188

Per person - min 2 pax

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4.7

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

One departure available

May

Starting from

€240

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

May - June

Starting from

€550

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 - Yacht sailing holidays & skippered tours in Italy

13737 reviews

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Barcolana 57: a day at the most famous regatta in the world

10/13/2025

Alessandro Marco B.

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Italy

All very nice. Antonio was an excellent skipper, very nice and helpful. Super crew! To be redone
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Liguria sailing

10/13/2025

anna m.

-

Switzerland

I spent three wonderful days on Marco's boat! Marco is an exceptional skipper: attentive, competent and able to immediately understand those who wanted to learn to sail and those who simply wanted to relax and enjoy the sea. The company was cheerful and engaging, and in a few hours a very special atmosphere of harmony and understanding was created. It is the skipper who makes the difference, and Marco has been able to grasp and satisfy everyone's needs, making this experience unforgettable."
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The sea and sailing in autumn: two days on Elba

10/13/2025

Roberto T.

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Italy

Ivo is a professional skipper. We had a technical outing that was very formative for me and we had fun.
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Poetic Gulf of Poets

10/9/2025

Massimo G.

-

Italy

Giovanni is a professional at his job,.. Expert, and collaborative with his customers... ADVICE....

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