Yacht sailing holidays & skippered tours in Italy
Discover more than 219 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
219
experiences
219
experiences
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,190
Per person
4.6
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€719
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€900
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
August
Starting from
€200
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
August
Starting from
€790
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€650
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€650
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€751
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
8 days - 7 nights
One departure available
August - September
€660
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
August
Starting from
€583
€525
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
August
Starting from
€935
€748
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€820
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.
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 more about the skipper and travellers who have already booked the holiday, to find out more about the
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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