
Yacht sailing holidays & skippered tours in Italy
Discover more than 153 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
153
experiences

4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
5 departures available
August - October
Starting from
€1,640
€1,558
Per person - min 2 pax

4.7
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
Starting from
€795
Per person

4.9
Italy: Aegadian islands
7 days - 7 nights
2 departures available
August - October
Starting from
€950
€855
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
Starting from
€600
€570
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August - October
Starting from
€590
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August - September
Starting from
€900
Per person

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
€1,041
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
August - September
Starting from
€950
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - October
Starting from
€690
Per person

5.0
Super!
Italy: Liguria
2 days - 1 night
2 departures available
August - September
€220
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August - September
€1,150
€1,035
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
August - September
Starting from
€583
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
14282 reviews
Sailing from Tuscany to South Corsica
07/26/2026
Serena P.
-
IT
Aeolian Islands: sun, sport, music, good food... The rest is magic!
07/26/2026
Benedetto R.
-
IT
Aeolian Islands: sun, sport, music, good food... The rest is magic!
07/26/2026
Camilla V.
-
IT
Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica
07/26/2026
Isaia N.
-
IT
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