Yacht sailing holidays & skippered tours in Italy
Discover more than 105 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
105
experiences
105
experiences
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
Give this experience a try!
€324
€360
Per person
4.3
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€329
Per person
4.3
Duration:
7 days - 6 nights
Italy:
Pontine Islands
+24 travellers
have booked
€1,090
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€375
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+2 travellers
have booked
Starting from
€280
Per person
4.5
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€280
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+13 travellers
have booked
Starting from
€325
Per person
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+14 travellers
have booked
€475
€500
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Amalfi Coast
+2 travellers
have booked
€333
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Southern Sardinia
+4 travellers
have booked
€553
€650
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+5 travellers
have booked
€280
€295
Per person
Duration:
2 days - 2 nights
Italy:
Liguria
+25 travellers
have booked
€190
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
10888 reviews
A weekend of sailing between Capraia and the island of Elba
03/20/2024
davide C.
-
Italy
Ventotene by sailing boat from Naples
10/16/2023
Manuela M.
Weekend of sea and colors between Ischia, Procida, Vivara and the Phlegraean fields
10/16/2023
Manuela M.
Aeolian Islands in Blue between sea and sky: Sun, sport, music, good food ... The rest is magic!
10/16/2023
Damien B.
-
Switzerland
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