
Yacht sailing holidays & skippered tours in Italy
Discover more than 92 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
92
experiences

4.7
Italy: Pontine Islands
3 days - 3 nights
One departure available
September
€420
Per person

4.9
Italy: Aegadian islands
7 days - 7 nights
One departure available
September - October
Starting from
€950
Per person

4.7
Premium
Italy: Northern Sardinia
7 days - 7 nights
3 departures available
September - October
Starting from
€1,640
€1,558
Per person - min 2 pax

5.0
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€212
Per person

4.8
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September - October
€700
Per person

5.0
Super!
Italy: Pontine Islands
5 days - 4 nights
One departure available
September
€550
Per person

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
€419
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
3 departures available
September - October
Starting from
€370
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
Starting from
€750
€675
Per person

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

4.8
Super!
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
€690
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
14989 reviews
Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY
09/9/2026
Giovanna G.
-
IT
Gargano National Park and Marine Protected Area of the Tremiti Islands
09/9/2026
Valentina D.
-
IT
Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper
09/9/2026
Massimiliano P.
-
IT
Amazing Pontine Islands on a sailboat with private bathrooms
09/9/2026
Elena B.
-
IT
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