Yacht sailing holidays & skippered tours in Italy
Discover more than 215 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
215
experiences
215
experiences
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
June - July
Starting from
€800
€720
Per person
4.6
Italy: Pontine Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€759
€683
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
June - August
Starting from
€650
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
June - July
Starting from
€935
€748
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
June - August
Starting from
€650
Per person
5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
3 departures available
July - August
Starting from
€750
€713
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
June - July
Starting from
€530
€477
Per person
4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
July - August
Starting from
€950
Per person
4.9
Italy: Tuscany
7 days - 7 nights
One departure available
July
Starting from
€700
Per person
4.9
Super!
Italy: Pontine Islands
3 days - 2 nights
2 departures available
July
Starting from
€370
€352
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
2 departures available
July
Starting from
€294
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
June - July
Starting from
€600
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
12322 reviews
Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)
06/14/2025
Linda H.
-
Australia
Life-changing experiences: Four days in the Pontine Islands
06/13/2025
Cristiano P.
-
Italy
Weekend at the Pontine a stone's throw from Rome
06/12/2025
armando a.
-
Switzerland
Weekend at the Pontine a stone's throw from Rome
06/12/2025
Daniela B.
-
Italy
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