Yacht sailing holidays & skippered tours in Italy
Discover more than 9 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
9
experiences
9
experiences
5.0
Italy: Aeolian Islands
7 days - 7 nights
One departure available
November
Starting from
€650
€585
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
October - November
€180
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
November
Starting from
€590
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
November
€299
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€420
Per person
Italy: Aeolian Islands
6 days - 6 nights
One departure available
November
Starting from
€600
Per person
Italy: Tuscany
1 day - 0 nights
7 departures available
October - November
Starting from
€115
Per person
4.2
Italy: Liguria
2 days - 1 night
5 departures available
November
€250
Per person
4.0
Italy: Sicily
6 days - 7 nights
5 departures available
November - December
€625
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
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
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