Yacht sailing holidays & skippered tours in Italy
Discover more than 143 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
143
experiences
143
experiences
5.0
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
August - September
Starting from
€275
€248
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
September
€600
Per person
4.8
Super!
Italy: Tuscany
3 days - 2 nights
2 departures available
September - October
Starting from
€240
€228
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September
€583
Per person
4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
August - September
Starting from
€590
Per person
4.9
Italy: Pontine Islands
4 days - 3 nights
One departure available
September
€270
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€750
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
September
Starting from
€220
Per person
4.8
Super!
Italy: Tuscany
4 days - 3 nights
One departure available
September
€360
€342
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
4 departures available
September - October
Starting from
€337
Per person
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
€419
Per person
4.6
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
September
Starting from
€750
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
13050 reviews
Four-day cruise to Elba or Capraia - Hostess on board
08/17/2025
Laura F.
-
Italy
Southern Sardinia on a beautiful 16m boat with HOSTESS
08/17/2025
Giorgio D.
A week of sailing and sea life on the island of Elba
08/17/2025
Valentina S.
-
Italy
Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms
08/17/2025
Pablo P.
-
Italy
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