Yacht sailing holidays & skippered tours in Italy
Discover more than 88 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
88
experiences
88
experiences
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
18 travellers
Starting from
€170
€200
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
18 travellers
Starting from
€342
€380
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
4 travellers
Starting from
€720
€800
Per person
4.9
Super!
Duration:
3 days - 2 nights
Italy:
Tuscany
32 travellers
Starting from
€275
€305
Per person
4.9
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
37 travellers
Starting from
€477
€530
Per person
5.0
Super!
Duration:
2 days - 2 nights
Italy:
Tuscany
34 travellers
Starting from
€264
€293
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
60 travellers
Starting from
€671
€745
Per person
5.0
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
123 travellers
Starting from
€585
€650
Per person
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
32 travellers
Starting from
€630
€700
Per person
4.7
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
91 travellers
Starting from
€585
€650
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Naples & Amalfi Coast
20 travellers
Starting from
€248
€275
Per person
Duration:
2 days - 1 night
Italy:
Tuscany
5 travellers
Starting from
€177
€197
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
12220 reviews
Weekend catamaran in Portovenere and Cinque Terre
05/12/2025
Davide S.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/12/2025
Stefano F.
-
Italy
Stuffed anchovies: magical weekend from Genoa
05/12/2025
Maurizio S.
1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK
05/8/2025
Maria Pia D.
-
Italy
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