Yacht sailing holidays & skippered tours in Italy
Discover more than 32 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
32
experiences
32
experiences
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
67 travellers
have left
Starting from
€850
€1,308
Per person
4.8
Duration:
4 days - 3 nights
Italy:
Tuscany
Alessandra G.
has left
€320
€390
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Tuscany
3 travellers
have left
€320
€390
Per person
Duration:
2 days - 2 nights
Italy:
Liguria
Give this experience a try!
€360
€400
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Naples & Amalfi Coast
Give this experience a try!
€198
€220
Per person
Duration:
7 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
Starting from
€405
€450
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aegadian islands
22 travellers
have left
€523
€550
Per person
4.6
Duration:
3 days - 2 nights
Italy:
Tuscany
7 travellers
have left
€275
€290
Per person
4.8
Duration:
3 days - 3 nights
Italy:
Tuscany
4 travellers
have left
€361
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
€433
Per person
4.6
Duration:
3 days - 3 nights
Italy:
Tuscany
3 travellers
have left
€370
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
36 travellers
have left
€240
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
12179 reviews
Magical weekend on Giglio Island
10/20/2024
Altamir T.
-
Brazil
Magical Barcolana Weekend: the most famous regatta!
10/15/2024
Antonio S.
-
Italy
Fantastic BARCOLANA: Racing in safety and joy!
10/15/2024
Nguyen Bao Duy T.
-
United Kingdom
We take part in the Barcolana: local skipper, regatta and lots of parties
10/15/2024
Danilo M.
-
Italy
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