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Yacht sailing holidays & skippered tours in Italy

Discover more than 41 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!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€590

Per person

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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

October - November

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

October

Starting from

€950

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

Starting from

€300

€270

Per person

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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

Starting from

€650

€585

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

One departure available

September - October

Starting from

€420

€399

Per person

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4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

€234

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€230

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€230

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€600

€540

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October

Starting from

€540

€513

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

October

Starting from

€800

€720

Per person

Why book a holiday with Sailsquare?

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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

13860 reviews

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Weekend of the Pontine Islands to discover Ponza and Palmarola

06/8/2026

Ilaria A.

Unforgettable experience! Marco and Giada are fantastic, attentive to everyone's needs, flexible and ready for any experience. The boat is home to it's nice to share every space. I wish you a journey like this, a journey of the soul between the waves of the sea and the waves of the wind.

Weekend of approach to sailing in the setting of the Gulf of Poets

06/8/2026

Chiara B.

-

IT

Fantastic weekend and experience absolutely to be repeated. Thanks to Commander Sandro! See you next time!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/8/2026

Laura S.

-

DE

Everything perfect - a particularly beautiful week
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2 June: Whale watching expedition with WWF guide on an 18-meter schooner

06/8/2026

Giovanna G.

-

IT

A fantastic experience for anyone who loves the sea and wants to discover more about its marine life.

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