Sailboat yacht sailing holidays & tours in Italy
Discover more than 164 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
164
experiences
164
experiences
5.0
Super!
Italy: Tuscany
2 days - 2 nights
7 departures available
September - October
Starting from
€275
€248
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
September
€600
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
9 departures available
August - October
Starting from
€337
Per person
4.8
Super!
Italy: Tuscany
3 days - 2 nights
2 departures available
September - October
Starting from
€240
€228
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September
€583
Per person
4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
August - September
Starting from
€690
€529
Per person
4.9
Italy: Pontine Islands
4 days - 3 nights
One departure available
September
€270
Per person
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
€419
Per person
4.8
Italy: Tuscany
6 days - 7 nights
One departure available
August
€900
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€750
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
4 departures available
September - October
Starting from
€220
Per person
4.8
Super!
Italy: Tuscany
4 days - 3 nights
One departure available
September
€360
€342
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 - Sailboat yacht sailing holidays & tours in Italy
12097 reviews
La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine
08/21/2025
Andrea P.
-
Italy
Weekend cruise from Trieste in Slovenia
08/20/2025
Nicola C.
-
Italy
A full day on a sailing boat in the Gulf of ALASSIO
08/20/2025
Patrizia F.
-
Italy
Life Changing Experiences - Pontine Islands in mid-August
08/20/2025
Ginevra S.
-
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 & SupportItaly: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964