Yacht sailing holidays & skippered tours in Italy
Discover more than 62 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
62
experiences
62
experiences
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
4 departures available
October
Starting from
€337
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€690
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October - November
€583
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
5 departures available
September - October
Starting from
€337
Per person
4.7
Italy: Tuscany
3 days - 2 nights
3 departures available
October
€200
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€200
€180
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
October
Starting from
€220
Per person
4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October
€299
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
3 departures available
October
Starting from
€294
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
2 departures available
September - October
€99
Per person
5.0
Super!
Italy: Lake Garda
2 days - 2 nights
One departure available
October
€179
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
2 departures available
October
Starting from
€59
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
13641 reviews
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
09/17/2025
Mauro Z.
-
Italy
Weekend at the Pontine aboard a splendid 16-meter sailboat
09/17/2025
Giulia E.
-
Italy
Egadi paradise for sailing and snorkeling
09/17/2025
Vicky H.
-
Belgium
A week in the Aeolian Islands - 6 islands in seven days
09/17/2025
Giuseppe I.
-
Italy
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