Yacht sailing holidays & skippered tours in Italy
Discover more than 151 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
151
experiences
151
experiences
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+8 travellers
have booked
€262
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
+13 travellers
have booked
€252
€265
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+34 travellers
have booked
€228
€240
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Lake Maggiore
Give this experience a try!
€181
€190
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+15 travellers
have booked
€260
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
cosetta
has booked
€265
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Liguria
+2 travellers
have booked
€275
Per person
4.2
Duration:
2 days - 2 nights
Italy:
Liguria
+5 travellers
have booked
Starting from
€250
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€1,350
Per person
4.4
Duration:
2 days - 1 night
Italy:
Liguria
+6 travellers
have booked
€200
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
€225
Per person
Duration:
2 days - 1 night
Italy:
Liguria
Give this experience a try!
€199
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
10894 reviews
A weekend of sailing between Capraia and the island of Elba
04/24/2024
Angelo C.
-
Italy
Easter on the Island of Elba
04/22/2024
Antonios S.
-
Italy
Trekking and sailing weekend on the island of Elba
04/22/2024
Sara C.
-
Italy
Luxury sailing in the Gulf of Poets
04/15/2024
Antonio C.
-
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!
Sailsquare
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964