
Yacht sailing holidays & skippered tours in Italy
Discover more than 48 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
48
experiences

4.8
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September - October
€700
Per person

4.7
Premium
Italy: Northern Sardinia
7 days - 7 nights
One departure available
September - October
Starting from
€1,640
€1,558
Per person - min 2 pax

5.0
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€212
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
Starting from
€230
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September - October
Starting from
€750
€675
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
One departure available
September
€790
Per person

4.8
Super!
Italy: Sicily
4 days - 3 nights
One departure available
September
€345
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€400
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
September - October
€370
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€300
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
Starting from
€230
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
September
€370
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
15070 reviews
Comfortably Aeolian Islands: Catamaran Cruise with Steward
09/21/2026
Pierluigi O.
-
IT
Mini-cruise with WWF guide in the heart of the Tuscan Archipelago
09/21/2026
Gioia S.
-
FR
Egadi Islands by catamaran
09/21/2026
Marco C.
-
IT
Learn to sail in Liguria: First level sailing course
09/21/2026
Valentina G.
-
IT
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