
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

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
October
Starting from
€590
Per person

4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
5 departures available
October - November
Starting from
€1,640
€1,558
Per person - min 2 pax

4.9
Italy: Aegadian islands
7 days - 7 nights
One departure available
October
Starting from
€950
Per person
4.7
Italy: Tuscany
2 days - 2 nights
5 departures available
October - November
Starting from
€300
€270
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September - October
Starting from
€650
€585
Per person

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
September - October
Starting from
€420
€399
Per person

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
€234
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€230
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€230
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October - November
Starting from
€600
€540
Per person

4.5
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October
Starting from
€540
€513
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
4 departures available
October
Starting from
€800
€720
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.
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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
13860 reviews
Weekend of the Pontine Islands to discover Ponza and Palmarola
06/8/2026
Ilaria A.
Weekend of approach to sailing in the setting of the Gulf of Poets
06/8/2026
Chiara B.
-
IT
Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!
06/8/2026
Laura S.
-
DE
2 June: Whale watching expedition with WWF guide on an 18-meter schooner
06/8/2026
Giovanna G.
-
IT
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