Yacht sailing holidays & skippered tours in Italy
Discover more than 59 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
59
experiences
59
experiences
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
5 departures available
September - October
Starting from
€337
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
4 departures available
October
Starting from
€337
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October - November
€583
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€690
Per person
4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
4 departures available
October - November
Starting from
€1,455
€1,382
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October
Starting from
€275
€248
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
3 departures available
October
Starting from
€363
€290
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
October
Starting from
€220
Per person
4.7
Italy: Pantelleria and Lampedusa
6 days - 7 nights
One departure available
October
Starting from
€930
€700
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
2 departures available
September - October
Starting from
€99
Per person
4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October
€299
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
October
€225
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
13484 reviews
Weekend only four guests - Elba Island
09/4/2025
Benedetta F.
-
Italy
Summer 2025 - Catamaran week in the Pontine Islands
09/4/2025
Barbara C.
-
Italy
ONE WAY From the Phlegraean to the Pontine Islands
09/4/2025
Eugenia C.
-
Italy
Between seas and volcanoes, fall in love with the Aeolian Islands
09/3/2025
Rocco P.
-
Italy
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