Yacht sailing holidays & skippered tours in Italy
Discover more than 41 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
41
experiences
41
experiences
4.9
Super!
Duration:
4 days - 3 nights
Italy:
Tuscany
+2 travellers
have booked
€479
€599
Per person
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
€855
€950
Per person
5.0
Duration:
7 days - 7 nights
Italy:
Aegadian islands
+9 travellers
have booked
Starting from
€531
€590
Per person
4.7
Duration:
3 days - 2 nights
Italy:
Tuscany
+50 travellers
have booked
Starting from
€239
€265
Per person
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€252
€280
Per person
4.9
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+53 travellers
have booked
Starting from
€450
€500
Per person
Duration:
7 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
Starting from
€540
€600
Per person
5.0
Duration:
2 days - 1 night
Italy:
Venice and the Gulf of Trieste
+8 travellers
have booked
Starting from
€171
€190
Per person
4.8
Duration:
8 days - 7 nights
Italy:
Pontine Islands
+12 travellers
have booked
Starting from
€585
€650
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aegadian islands
+19 travellers
have booked
Starting from
€523
€550
Per person
4.0
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
+128 travellers
have booked
Starting from
€1,701
€1,790
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Pantelleria and Lampedusa
+23 travellers
have booked
Starting from
€713
€750
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
11321 reviews
Discover the Aeolian Islands and their wonders
07/27/2024
edoardo c.
-
Italy
Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor
07/27/2024
Micaela Z.
-
Italy
Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor
07/26/2024
Katia P.
-
Italy
4 days in the Pontine Islands (sailing school)
07/26/2024
valentina P.
-
Luxembourg
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