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Yacht sailing holidays & skippered tours in Italy

Discover more than 34 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!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - August

Starting from

€660

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

July - August

Starting from

€990

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

5 departures available

July - August

Starting from

€754

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

July

Starting from

€801

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

June - August

Starting from

€1,150

Per person

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5.0

Super!

Week in Ponza Palmarola and Ventotene COMODI – Max 4 people

Italy: Pontine Islands

6 days - 6 nights

3 departures available

July - August

Starting from

€1,028

€874

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

5 departures available

July - August

Starting from

€641

Per person

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4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

4 departures available

July - August

Starting from

€700

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

4 departures available

July - August

Starting from

€850

€765

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

5 departures available

July - August

Starting from

€778

€700

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

5 departures available

July - August

Starting from

€1,320

€1,056

Per person - min 2 pax

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5.0

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

One departure available

July

Starting from

€1,132

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.

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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

15141 reviews

A taste of the magnificent Island of Elba

10/14/2026

Annachiara P.

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IT

It was a beautiful weekend!! Alberto is an experienced and prepared skipper who is totally dedicated to what he is passionate about. We really appreciated his willingness to meet us and, compatibly with weather conditions and times, to adapt the weekend to our needs: although we were licensed, we needed to regain confidence with going to sea (sailing!), without giving up relaxation. Alberto was a great teacher and we learned so much! He took us to beautiful places and we really enjoyed our time together (and the classical guitar under the stars added that extra touch :D). A special thanks to Claudia for her company and for the super aperitifs she prepared for us! The boat is beautiful, maintained with great care, order and cleanliness. They were two wonderful days. Thank you very much Alberto and Claudia!! We hope to repeat it soon!
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Sailing and Trekking in the Aeolian Islands

10/14/2026

Massimo G.

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IT

A week in full relaxation in the Aeolian Islands.Mario is a professional and helpful skipper with his customers, putting them immediately at ease, For your holiday in this archipelago I highly recommend to contact him .... MARIO

Barcolana Weekend: experience the largest regatta in the world

10/13/2026

Francesco S.

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IT

Ilaria in a nutshell Great skipper Great cook Super nice

Sailing and Trekking in the Aeolian Islands

10/12/2026

Filippo D.

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IT

I was lucky enough to have a "sailing + trekking" experience aboard Mario's beautiful boat. He is a true expert in sailing and the Aeolian Islands! He is also very willing to teach and explain all the technicalities related to this fascinating world. The boat is maniacally maintained and is very comfortable I recommend it

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