Yacht sailing holidays & skippered tours in Italy
Discover more than 2 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
2
experiences
2
experiences
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
€1,251
€1,390
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
2 travellers
Starting from
€972
€1,080
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.
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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
12217 reviews
1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK
05/8/2025
Maria Pia D.
-
Italy
A long weekend of sea and freedom from Argentario to Elba
05/7/2025
RAFFAELE L.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2025
Leonardo R.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2025
Simone S.
-
Italy
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