
Yacht sailing holidays & skippered tours in Italy
Discover more than 45 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
45
experiences

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

5.0
Super!
Italy: Liguria
2 days - 1 night
One departure available
October
€220
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
Starting from
€750
€675
Per person
4.1
Italy: Tuscany
2 days - 2 nights
5 departures available
October - November
€300
€270
Per person

4.0
New
Italy: Pantelleria and Lampedusa
7 days - 7 nights
2 departures available
October - November
€500
€348
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October - November
€250
Per person

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

4.7
Italy: Pantelleria and Lampedusa
6 days - 7 nights
One departure available
October
Starting from
€860
Per person

4.4
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October
Starting from
€540
€513
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€230
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
14436 reviews
2 boats in Costa Smeralda and Bonifacio aboard a 16-meter traditional sailing yacht.
08/9/2026
Claudia D.
-
IT
Between the Pontine Islands and the Phlegraean Islands by Sailing Boat
08/9/2026
Silvia S.
-
IT
Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY
08/9/2026
Fabio Valerio R.
-
CH
Sailing holiday in the turquoise blue waters of Corsica
08/9/2026
Fedra M.
-
IT
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