Yacht sailing holidays & skippered tours in Italy
Discover more than 389 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
389
experiences
389
experiences
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
19 travellers
Starting from
€975
€1,500
Per person
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
8 travellers
€1,512
€1,890
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
62 travellers
€990
€1,190
Per person
5.0
Super!
Duration:
4 days - 4 nights
Italy:
Tuscany
Give this experience a try!
€380
€460
Per person
5.0
Super!
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€1,275
€1,500
Per person
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€353
€415
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Pantelleria and Lampedusa
34 travellers
€595
€700
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
28 travellers
Starting from
€667
€785
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
12 travellers
Starting from
€170
€200
Per person
4.5
Duration:
4 days - 4 nights
Italy:
Pontine Islands
Give this experience a try!
€378
€420
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
17 travellers
Starting from
€342
€380
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
2 travellers
Starting from
€720
€800
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
12204 reviews
First spring getaways in the company of the sea
04/29/2025
Raffaella Valeria R.
-
Italy
25 April long weekend between Capraia and Northern Corsica
04/29/2025
VERONICA D.
-
Italy
Day trip with aperitif at sunset!
04/28/2025
Silvia Maddalena V.
-
Italy
25 April long weekend between Capraia and Northern Corsica
04/28/2025
Luigi C.
-
Italy
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