Yacht sailing holidays & skippered tours in Italy
Discover more than 133 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
133
experiences
133
experiences
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+8 travellers
have booked
€523
€550
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
€417
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+4 travellers
have booked
Starting from
€499
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+2 travellers
have booked
€90
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+4 travellers
have booked
€1,100
Per person
4.8
Duration:
4 days - 4 nights
Italy:
Tuscany
+3 travellers
have booked
€490
Per person
4.8
Duration:
5 days - 4 nights
Italy:
Tuscany
+6 travellers
have booked
€490
Per person
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
Give this experience a try!
Starting from
€650
Per person
4.5
Duration:
3 days - 4 nights
Italy:
Tuscany
Elettra
has booked
€350
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
Give this experience a try!
€324
€360
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€314
€330
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€360
Per person
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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
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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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