Yacht sailing holidays & skippered tours in Italy
Discover more than 46 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
46
experiences
46
experiences
4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
October
Starting from
€200
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October - November
Starting from
€530
€477
Per person
4.8
Super!
Italy: Pantelleria and Lampedusa
6 days - 7 nights
2 departures available
October
Starting from
€850
€808
Per person
4.9
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September - October
Starting from
€751
Per person
4.8
Italy: Tuscany
3 days - 2 nights
One departure available
September - October
Starting from
€260
€247
Per person
4.8
Italy: Aeolian Islands
5 days - 4 nights
2 departures available
October
€590
Per person
4.7
Premium
Italy: Northern Sardinia
7 days - 7 nights
4 departures available
October - November
Starting from
€1,455
€1,382
Per person
4.2
Italy: Liguria
2 days - 2 nights
2 departures available
October
Starting from
€265
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
October
Starting from
€400
€360
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
3 departures available
October
Starting from
€294
Per person
4.8
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
October
Starting from
€615
Per person
5.0
Italy: Pontine Islands
3 days - 2 nights
4 departures available
October
Starting from
€337
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
12482 reviews
On board with the chef at the Egadi Islands
07/6/2025
Loredana R.
-
Italy
Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!
07/6/2025
Maila L.
A week in the Aeolian Islands - 6 islands in seven days
07/6/2025
Rosario L.
-
Italy
Aperitif Trip to the Gulf of Tigullio - All inclusive!
07/6/2025
alice b.
-
Italy
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