Yacht sailing holidays & skippered tours in Italy
Discover more than 215 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
215
experiences
215
experiences
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,190
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€900
Per person
4.6
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€719
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€650
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
August
Starting from
€200
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€650
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
August
Starting from
€583
€525
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
August - September
Starting from
€751
Per person
4.7
Italy: Tuscany
6 days - 6 nights
2 departures available
August - September
Starting from
€1,041
€989
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€615
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€820
Per person
4.8
Italy: Aeolian Islands
6 days - 7 nights
4 departures available
August - September
Starting from
€530
€504
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
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
12607 reviews
Four days of sea, nature and fun in the Pontine Islands!
07/19/2025
CLAUDIO G.
-
Italy
Tour of Elba and Capraia on a Catamaran
07/19/2025
Rosario C.
-
Italy
Pontine Islands aboard a splendid 16-meter sailboat
07/19/2025
Paola G.
-
Italy
Aeolian Islands: blue seen from a sailboat
07/19/2025
nicole b.
-
Italy
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