Yacht sailing holidays & skippered tours in Italy
Discover more than 29 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
29
experiences
29
experiences
4.9
Duration:
3 days - 2 nights
Italy:
Tuscany
+6 travellers
have booked
Starting from
€333
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Tuscany
+4 travellers
have booked
€240
Per person
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+20 travellers
have booked
€390
€410
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+8 travellers
have booked
€239
€265
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
+14 travellers
have booked
€237
€249
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€225
Per person
Duration:
2 days - 2 nights
Italy:
Liguria
+37 travellers
have booked
€190
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
€225
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+14 travellers
have booked
€180
Per person
4.8
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+23 travellers
have booked
€730
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+8 travellers
have booked
€450
€500
Per person
4.0
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
+108 travellers
have booked
Starting from
€1,701
€1,790
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
10905 reviews
May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms
05/2/2024
susanna s.
-
Italy
25 April - Whale watching expedition with WWF researcher in Liguria
05/2/2024
Rossella D.
-
Italy
LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba
05/1/2024
Simone D.
-
Switzerland
Long weekend in Capraia and North Corsica
04/30/2024
Licio M.
-
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