Yacht sailing holidays & skippered tours in Italy
Discover more than 12 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
12
experiences
12
experiences
4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
November
€299
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
November
€190
Per person
4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€420
Per person
4.8
Italy: Tuscany
2 days - 2 nights
One departure available
October - November
€300
Per person
3.0
Italy: Aeolian Islands
6 days - 6 nights
One departure available
November
Starting from
€600
Per person
Italy: Liguria
1 day - 0 nights
18 departures available
October - November
€86
Per person
Italy: Naples & Amalfi Coast
1 day - 0 nights
3 departures available
October
Starting from
€110
€88
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
Italy: Liguria
3 days - 2 nights
5 departures available
October - November
€250
Per person
4.9
Italy: Aeolian Islands
7 days - 7 nights
One departure available
November
€650
€585
Per person
4.1
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
13632 reviews
Week-end all'Elba - Hostess a bordo
09/17/2025
Riccardo A.
-
Italy
A week in the Aeolian Islands - 6 islands in seven days
09/17/2025
Sarah N.
-
Italy
South Corsica: blue seen from a sailboat
09/17/2025
anna m.
-
France
Egadi paradise for sailing and snorkeling
09/17/2025
MARYLENE E.
-
France
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