Yacht sailing holidays & skippered tours in Italy
Discover more than 44 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
44
experiences
44
experiences
4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
October
Starting from
€200
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September - October
Starting from
€751
Per person
4.8
Super!
Italy: Pantelleria and Lampedusa
6 days - 7 nights
2 departures available
October
Starting from
€850
€808
Per person
4.8
Italy: Aeolian Islands
5 days - 4 nights
2 departures available
October
€590
Per person
4.8
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
October
Starting from
€615
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
October
Starting from
€400
€360
Per person
4.8
Italy: Tuscany
3 days - 2 nights
One departure available
September - October
Starting from
€240
€228
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
3 departures available
October
Starting from
€294
Per person
5.0
Italy: Pontine Islands
3 days - 2 nights
4 departures available
October
Starting from
€337
Per person
4.2
Italy: Liguria
2 days - 2 nights
2 departures available
October
Starting from
€265
Per person
5.0
Italy: Pontine Islands
4 days - 3 nights
5 departures available
September - October
Starting from
€337
Per person
4.7
Premium
Italy: Northern Sardinia
7 days - 7 nights
4 departures available
October - November
Starting from
€1,455
€1,382
Per person
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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.
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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
12580 reviews
We have known the Aeolian Islands for 20 years, live them with us!
07/15/2025
Arianna O.
Life-changing experiences - Escape to the Pontine Islands
07/15/2025
Anna R.
-
Italy
Weekend on Elba Island
07/15/2025
Dalgisa B.
-
Italy
Long weekend among the queens of the archipelago - Elba and Capraia
07/15/2025
Laurence B.
-
Belgium
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