Yacht sailing holidays & skippered tours in Italy
Discover more than 238 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
238
experiences
238
experiences
5.0
Duration:
7 days - 7 nights
Italy:
Aegadian islands
+6 travellers
have booked
Starting from
€624
Per person
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
€1,690
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Northern Sardinia
+13 travellers
have booked
€1,490
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Tuscany
+10 travellers
have booked
Starting from
€520
Per person
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+12 travellers
have booked
€562
€624
Per person
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
Give this experience a try!
€750
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
Asley
has booked
€675
€750
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
Starting from
€1,000
Per person
4.0
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
+108 travellers
have booked
€1,790
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+5 travellers
have booked
€645
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+8 travellers
have booked
Starting from
€495
€550
Per person
4.5
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+6 travellers
have booked
Starting from
€360
Per person
Why book a holiday with Sailsquare?
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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
10907 reviews
25 April - 4 days sailing between La Maddalena and Bonifacio
05/3/2024
Bart S.
-
Spain
Sailing, early sun and aperitif at sunset ... What else?
05/3/2024
Cristiana L.
-
Italy
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
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