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Sailboat yacht sailing holidays & tours in Italy

Discover more than 182 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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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

3 departures available

August - October

€690

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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5.0

Super!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

Per person

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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

13361 reviews

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Midweek sailing trip: two days at sea in Alassio

08/13/2026

Alvaro B.

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IT

skipper Daniele with hospitable sailing experience Very nice and comfortable boat, great decision to sleep in the air-conditioned harbor A tip: for lunch on the boat I recommend agreeing on the menu beforehand otherwise you run the risk of having two identical lunches For the rest it was a really good experience
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Two days at the Tremiti Marine Protected Area

08/13/2026

Anna M.

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IT

The boat and the service could be improved.... The tremors are much more than what we have seen, the sail is something else. High cost to experience. Skipper too apprehensive and not very empathetic puts you a little anxious puts you in awe and you don't enjoy your holiday Despite some very welcome gestures of courtesy, the feeling of unease prevailed. Would not recommend

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/13/2026

francesco b.

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IT

The trip was unique in its kind for the good relationship that was created between the crew of the boat. For me it was an authentic and fun experience that for a week makes you think of nothing else
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A week sailing in the most beautiful places in the world

08/13/2026

Elena T.

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IT

Piero and Giusy are the best that a sailing experience can offer. Excellent sailors, they give the opportunity to try and apply themselves in maneuvers if you wish. Excellent guides and connoisseurs of the area, it is easy to get lost talking about anything with them. Finally, Giusy's ability in the kitchen and in the management of the kitchen / galley is something that borders on perfection. You can't ask for anything better. Priceless availability, patience and kindness!! ❤️❤️❤️

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