Yacht sailing holidays & skippered tours in Italy
Discover more than 175 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
175
experiences
175
experiences
4.8
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
142 travellers
Starting from
€475
€500
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
12 travellers
Starting from
€950
€1,000
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
19 travellers
Starting from
€333
€350
Per person
4.0
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
39 travellers
Starting from
€451
€475
Per person
5.0
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
26 travellers
Starting from
€475
€500
Per person
4.8
Super!
Duration:
6 days - 6 nights
Italy:
Naples & Amalfi Coast
8 travellers
€1,316
€1,385
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Tuscany
42 travellers
Starting from
€989
€1,041
Per person
4.6
Premium
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
256 travellers
Starting from
€1,026
€1,080
Per person
4.8
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
35 travellers
Starting from
€646
€680
Per person - min 2 pax
4.8
Super!
Duration:
6 days - 7 nights
Italy:
Pantelleria and Lampedusa
79 travellers
Starting from
€808
€850
Per person
4.6
Duration:
6 days - 6 nights
Italy:
Tuscany
69 travellers
Starting from
€989
€1,041
Per person
4.9
Super!
Duration:
3 days - 2 nights
Italy:
Pontine Islands
55 travellers
Starting from
€352
€370
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
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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