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Yacht sailing holidays & skippered tours in Italy

Discover more than 22 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

4 departures available

September - October

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

3 departures available

September

Starting from

€990

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

3 departures available

September

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

3 departures available

September

Starting from

€700

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

September - October

Starting from

€778

€700

Per person

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4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

September - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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4.8

New

Cruise in southern Sardinia: charm and turquoise waters in schooner with hostess and full board

Italy: Southern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€1,098

Per person

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4.2

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€780

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€690

Per person

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New

Premium

All inclusive sailing cruise on Lagoon42 Catamaran in Sardinia with hostess

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

September - October

Starting from

€2,200

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

4 departures available

September - October

Starting from

€1,495

€1,346

Per person - min 2 pax

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September

Starting from

€850

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

15149 reviews

It's time for sun and sea!

11/5/2026

francesca t.

-

IT

All very nice !! and Carlo... A very good sailor and a very kind and hospitable person !! Francesca
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Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

11/3/2026

Paolo P.

-

IT

Excellent experience, boat up to expectations, skipper attentive to the safety of the crew and always available to evaluate every request of the people on board. To repeat the adventure for other destinations.
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Squid Festival 2026! - Capraia Isola

11/3/2026

Andrea C.

-

IT

Good experience, too bad for the weather conditions not ideal.

Squid Regatta

10/20/2026

Valentina M.

-

IT

Wonderful weekend with participation in the squid regatta that allowed us to appreciate Francesco's skills as a captain. It was fun to get involved in conducting! [hidden] is a gem of a boat: convenient spaces, clean and comfortable.

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