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Sailboat yacht sailing holidays & tours in Italy

Discover more than 208 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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5.0

Super!

Sailing weekend in Liguria

Italy: Liguria

2 days - 1 night

5 departures available

August - September

€225

Per person

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4.9

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

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4.8

Super!

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€850

Per person

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Southern Sardinia on a beautiful 16m boat with HOSTESS

Italy: Southern Sardinia

7 days - 7 nights

3 departures available

August

Starting from

€1,500

€1,350

Per person

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4.7

Long weekend of whale watching with WWF guide between Liguria and the French Riviera

Italy: Liguria

3 days - 3 nights

One departure available

September

€441

Per person

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4.4

Enjoy the Aeolian Islands with skipper and hostess

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€940

Per person

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5.0

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€540

Per person

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5.0

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August - October

Starting from

€559

Per person

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Magical Pontine: full sail to discover the archipelago

Italy: Pontine Islands

3 days - 3 nights

One departure available

August

€400

Per person

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5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€337

Per person

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4.6

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

2 departures available

August - September

€650

Per person

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4.9

Ten days from Catania to the Aeolian Islands on a luxury sailboat

Italy: Sicily

9 days - 10 nights

One departure available

August

€1,300

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 yacht sailing holidays & tours in Italy

11729 reviews

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Four-day cruise to Elba or Capraia - Hostess on board

08/1/2025

Veronica M.

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Italy

Vittorio and Giulia, two fantastic people made us feel at home, showing us wonderful places and pampering us as if we were family!! Highly recommended and for us to be repeated... Thanks again from us. Veronica and Pierluigi
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Midweek relaxing in the Pontine Mountains

08/1/2025

Valentina P.

First experience with Salisquare: everything went very well despite the adverse weather on the first day. Mirko is a crazy Skipper, safe, precise, excellent cook, nice, kind and helpful! The boat is also wonderful! Great company! Truly a wonderful experience, to be done again!
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North Corsica & Tuscan Archipelago: we love to travel a lot

08/1/2025

Sandro G.

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Italy

Beautiful week. To be repeated for sure. The skipper Marco as well as being competent is also very nice and engaging in everything. Thank you again and see you for next year.
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/1/2025

Michele A.

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Netherlands

Fantastic places (and we knew this), high-level company, spacious and well-maintained boat, experienced and safe skipper and co-skipper, despite the young age, excellent food, guaranteed aperitifs, what else could you want? Luca and Tommaso took care of us and allowed us to spend a fantastic week on the [hidden], all absolutely recommended.

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