Yacht sailing holidays & skippered tours in Italy
Discover more than 238 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
238
experiences
238
experiences
4.3
Duration:
6 days - 6 nights
Italy:
Pontine Islands
+6 travellers
have booked
€790
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Tuscany
+4 travellers
have booked
€299
Per person
4.3
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€410
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+8 travellers
have booked
€420
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€462
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+15 travellers
have booked
€362
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+42 travellers
have booked
€415
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€330
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+30 travellers
have booked
€351
€390
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
+58 travellers
have booked
Starting from
€85
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Pontine Islands
+8 travellers
have booked
€450
Per person
4.8
Duration:
3 days - 2 nights
Italy:
Amalfi Coast
+15 travellers
have booked
€333
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
10913 reviews
Weekend in Capraia, the island with timeless sunsets
05/7/2024
Irene T.
-
Italy
Week End Basic and Advanced Sailing Course
05/7/2024
Federico B.
-
Italy
1st May - Whale watching cruise with WWF researcher between Elba and Capraia
05/6/2024
Elettra B.
-
Italy
Catamaran weekend: La Spezia, Portovevere, Lerici and Cinque Terre
05/6/2024
Paola d.
-
Italy
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