
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

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
July - August
Starting from
€689
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - August
Starting from
€625
Per person

4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
4 departures available
July - August
Starting from
€950
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
July - August
Starting from
€600
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
July - August
Starting from
€600
€540
Per person

4.9
Super!
Italy: Tuscany
4 days - 3 nights
5 departures available
July - August
Starting from
€430
€409
Per person

4.9
Super!
Italy: Tuscany
7 days - 7 nights
4 departures available
July - August
Starting from
€700
Per person

4.8
Super!
Italy: Pontine Islands
4 days - 3 nights
5 departures available
June - July
Starting from
€210
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
July
Starting from
€800
€720
Per person

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
5 departures available
June - July
Starting from
€450
€428
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
4 departures available
July - August
Starting from
€793
€714
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
One departure available
July
Starting from
€272
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
13745 reviews
Weekend in Capraia, the island with timeless sunsets
10/22/2025
Don D.
-
Italy
Relaxing weekend between Portovenere and the 5 Terre
10/21/2025
Manuela S.
-
Italy
A day sailing in the fantastic Gulf of Trieste
10/20/2025
Monica C.
-
Italy
We have known the Aeolian Islands for 20 years. - Live them with us.
10/20/2025
Marco F.
-
Italy
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