
Yacht sailing holidays & skippered tours in Italy
Discover more than 43 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
43
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - September
Starting from
€660
Per person

4.8
Super!
Italy: Tuscany
6 days - 6 nights
5 departures available
July - September
Starting from
€990
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
6 days - 6 nights
One departure available
August
Starting from
€1,150
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
July - September
Starting from
€1,450
€1,305
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
5 departures available
August - September
Starting from
€800
Per person
5.0
Super!
Italy: Pontine Islands
6 days - 6 nights
4 departures available
July - August
Starting from
€1,028
€874
Per person

4.9
Super!
Italy: Tuscany
7 days - 7 nights
5 departures available
July - September
Starting from
€641
Per person

4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
5 departures available
July - September
Starting from
€700
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
5 departures available
July - September
Starting from
€850
€765
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
5 departures available
July - September
Starting from
€778
€700
Per person

4.4
Premium
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - September
Starting from
€1,525
€1,373
Per person - min 2 pax

4.9
Italy: Liguria
1 day - 0 nights
5 departures available
July - August
€130
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
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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
Feast of Santa Candida in Ventotene
11/9/2026
Gennaro A.
-
IT
It's time for sun and sea!
11/5/2026
francesca t.
-
IT
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
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