
Yacht sailing holidays & skippered tours in Italy
Discover more than 74 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
74
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
June - July
Starting from
€700
Per person

4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
One departure available
June - July
Starting from
€1,640
€1,558
Per person - min 2 pax

4.9
Italy: Aegadian islands
7 days - 7 nights
One departure available
June - July
Starting from
€950
Per person

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

5.0
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
June - July
Starting from
€950
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
June - July
Starting from
€690
Per person

5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
One departure available
June - July
Starting from
€790
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
One departure available
June
Starting from
€490
€466
Per person

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
June - July
Starting from
€700
Per person

5.0
Super!
Italy: Aeolian Islands
3 days - 2 nights
2 departures available
June
Starting from
€390
€351
Per person

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
One departure available
June - July
Starting from
€900
€765
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
2 departures available
June - July
Starting from
€490
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
13942 reviews
Week 2 June in the Egadi Islands between Nature, Relaxation & Fun
06/21/2026
Giovanni P.
-
IT
Sail to the Aeolian Islands with an experienced crew on a catamaran!
06/21/2026
Barbara M.
-
IT
We have known the Aeolian Islands for 20 years, live them with us!
06/21/2026
Anna M.
-
IT
The wild south from Cagliari to CarloForte
06/21/2026
Danila G.
-
SM
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