Yacht sailing holidays & skippered tours in Italy
Discover more than 204 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
204
experiences
204
experiences
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
One departure available
July - August
Starting from
€650
Per person
5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
July - August
Starting from
€900
€810
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
One departure available
July - August
Starting from
€650
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
July
Starting from
€530
€477
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
July - August
Starting from
€690
€621
Per person
4.9
Italy: Tuscany
7 days - 7 nights
One departure available
July
€700
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
8 days - 7 nights
One departure available
July
Starting from
€660
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
July
Starting from
€780
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
July
Starting from
€935
€748
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
July
Starting from
€293
€264
Per person
4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
July - August
Starting from
€950
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
12432 reviews
6 days of Elba, Capraia and Corsica
06/30/2025
Stefano M.
-
Switzerland
Life-changing experiences - Escape to the Pontine Islands
06/30/2025
Angela C.
-
Italy
Weekend di emozioni nel Blu Pontino
06/30/2025
Giulia D.
-
Italy
The pearls of Liguria: Portoverne, Lerici and the Gulf of Poets
06/30/2025
Alice C.
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & SupportLet's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964