
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

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
October
Starting from
€453
Per person

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

5.0
Super!
Italy: Sicily
1 day - 0 nights
23 departures available
October
€150
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October - November
€300
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
October
€230
Per person

4.9
Super!
Italy: Aegadian islands
3 days - 2 nights
4 departures available
October - November
€350
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
2 departures available
October
€370
Per person

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

4.8
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October
€200
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
October
€230
Per person

4.5
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€290
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
One departure available
October
€585
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
15136 reviews
Sailing in the magical Sardinia of the South
10/8/2026
Sebastiano F.
-
IT
Experience the sea in October!
10/6/2026
Luigi V.
-
IT
Aeolian Islands: between sea and authentic flavours
10/5/2026
Giorgia P.
-
IT
Maddalena Archipelago, southern Corsica: wonderful Sardinia
10/5/2026
Michelle B.
-
US
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