
Yacht sailing holidays & skippered tours in Italy
Discover more than 28 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
28
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
June - July
Starting from
€660
Per person

4.8
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
June - July
Starting from
€990
Per person

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
June - July
Starting from
€801
Per person

5.0
Super!
Italy: Northern Sardinia
5 days - 4 nights
One departure available
May - June
€450
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
6 days - 6 nights
2 departures available
June - July
Starting from
€1,150
Per person

4.9
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
June - July
Starting from
€641
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
3 departures available
June - July
Starting from
€778
€700
Per person
4.1
Italy: Tuscany
2 days - 2 nights
4 departures available
June
Starting from
€275
€248
Per person
4.1
Italy: Tuscany
4 days - 4 nights
2 departures available
June
€1,400
Per person

4.4
Premium
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
May - July
Starting from
€1,525
€1,373
Per person - min 2 pax

5.0
Italy: Tuscany
7 days - 6 nights
2 departures available
June - July
Starting from
€1,132
Per person

4.8
New
Italy: Southern Sardinia
6 days - 6 nights
5 departures available
May - July
Starting from
€1,098
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
15149 reviews
It's time for sun and sea!
11/5/2026
francesca t.
-
IT
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
Squid Regatta
10/20/2026
Valentina M.
-
IT
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