Yacht sailing holidays & skippered tours in Italy
Discover more than 145 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
145
experiences
145
experiences
4.6
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
Starting from
€719
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
August - September
Starting from
€650
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
September
Starting from
€650
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
August - September
Starting from
€690
€621
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
August - October
Starting from
€751
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
September
Starting from
€293
€264
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
September - October
Starting from
€530
€477
Per person
4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
September - October
Starting from
€950
Per person
4.8
Super!
Italy: Pantelleria and Lampedusa
6 days - 7 nights
5 departures available
August - October
Starting from
€850
€808
Per person
4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
Starting from
€1,041
€989
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
August - September
Starting from
€689
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
8 days - 7 nights
One departure available
August - September
Starting from
€660
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
12518 reviews
Weekend only four guests - Elba Island
07/9/2025
Paola F.
-
Italy
Sailing weekend in the Pontine Islands
07/9/2025
Antonio F.
-
Italy
Between seas and volcanoes, fall in love with the Aeolian Islands
07/8/2025
Marco C.
-
Italy
Capri LightBlue and Positano BluSKy
07/8/2025
Marianna D.
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