Yacht sailing holidays & skippered tours in Italy
Discover more than 240 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
240
experiences
240
experiences
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+2 travellers
have booked
Starting from
€1,500
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Southern Sardinia
Give this experience a try!
€711
€790
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+5 travellers
have booked
Starting from
€899
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+6 travellers
have booked
Starting from
€550
Per person
4.5
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+6 travellers
have booked
Starting from
€360
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
+114 travellers
have booked
€650
Per person
4.0
Duration:
6 days - 7 nights
Italy:
Amalfi Coast
+6 travellers
have booked
€1,250
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Pontine Islands
Give this experience a try!
€616
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+12 travellers
have booked
Starting from
€580
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
+35 travellers
have booked
Starting from
€650
Per person
3.5
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+3 travellers
have booked
€585
€650
Per person
Duration:
6 days - 7 nights
Italy:
Pantelleria and Lampedusa
Give this experience a try!
€800
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
10916 reviews
Weekend with wine tasting between Santa Margherita Ligure and Portofino
05/7/2024
Valentina B.
-
Italy
Week End Basic and Advanced Sailing Course
05/7/2024
Antonio R.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2024
enrico g.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2024
Irene T.
-
Italy
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