Yacht sailing holidays & skippered tours in Italy
Discover more than 78 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
78
experiences
78
experiences
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
June - July
€750
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
June - July
Starting from
€530
€477
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
June - July
Starting from
€650
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
June - July
Starting from
€935
€748
Per person
4.7
Italy: Liguria
5 days - 6 nights
One departure available
June - July
Starting from
€798
€758
Per person
5.0
Italy: Aeolian Islands
7 days - 7 nights
One departure available
June - July
Starting from
€650
€585
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
June - July
Starting from
€600
Per person
4.8
Italy: Aeolian Islands
6 days - 7 nights
One departure available
June - July
Starting from
€530
€504
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
June - July
Starting from
€689
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
One departure available
June - July
Starting from
€615
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
June - July
Starting from
€620
Per person
4.8
Italy: Pontine Islands
4 days - 3 nights
One departure available
June - July
Starting from
€270
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
12396 reviews
Life-changing experiences - Escape to the Pontine Islands
06/27/2025
Nita C.
-
Italy
Long weekend of whale watching with WWF guide between Golfo Paradiso and Gulf of Tigullio
06/26/2025
Lovotti L.
-
Italy
Whale watching cruise with WWF guide between Elba, Pianosa and the canyons of Corsica
06/25/2025
Maria Giuseppina F.
-
Italy
The pearls of Liguria: Portoverne, Lerici and the Gulf of Poets
06/25/2025
Manuela G.
-
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