Yacht sailing holidays & skippered tours in Italy
Discover more than 179 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
179
experiences
179
experiences
4.8
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
August - September
Starting from
€1,875
€1,219
Per person
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€1,890
€1,512
Per person
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,190
€990
Per person
4.7
Italy: Tuscany
6 days - 5 nights
4 departures available
August
Starting from
€750
€638
Per person
4.6
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
August - September
Starting from
€785
€667
Per person
5.0
Super!
Italy: Liguria
3 days - 2 nights
5 departures available
August
Starting from
€200
€170
Per person
Italy: Tuscany
6 days - 5 nights
3 departures available
August - September
Starting from
€1,000
€850
Per person
Italy: Sicily
2 days - 2 nights
2 departures available
August
Starting from
€500
€450
Per person
4.8
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August
Starting from
€910
€819
Per person - min 2 pax
4.3
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€800
€720
Per person
Italy: Aegadian islands
6 days - 6 nights
2 departures available
August
Starting from
€950
€855
Per person
4.9
Super!
Italy: Tuscany
7 days - 6 nights
5 departures available
August - September
Starting from
€700
€630
Per person
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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
12226 reviews
A day on a sailing boat to Gallinara Island or the Dianese Gulf
05/21/2025
Roberta N.
-
Italy
A day on a sailing boat to Gallinara Island or the Dianese Gulf
05/20/2025
Sabrina L.
-
Italy
Weekend of relaxation and fun from Genoa
05/20/2025
Patrizia S.
-
Italy
A day sailing in the fantastic Gulf of Trieste
05/20/2025
dino m.
-
Italy
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