Yacht sailing holidays & skippered tours in Italy
Discover more than 130 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
130
experiences
130
experiences
4.7
Duration:
6 days - 7 nights
Italy:
Pontine Islands
Give this experience a try!
€941
€990
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
Starting from
€561
€590
Per person
4.7
Duration:
6 days - 7 nights
Italy:
Campania
+16 travellers
have booked
€1,040
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+4 travellers
have booked
Starting from
€599
Per person
4.9
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
Give this experience a try!
€665
€700
Per person
4.7
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
Give this experience a try!
€760
€800
Per person
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
Give this experience a try!
€570
€600
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+41 travellers
have booked
€900
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
€1,000
Per person
4.5
Duration:
7 days - 8 nights
Italy:
Aegadian islands
+38 travellers
have booked
Starting from
€600
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+6 travellers
have booked
Starting from
€600
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Pontine Islands
+19 travellers
have booked
Starting from
€989
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
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