
Sailboat yacht sailing holidays & tours in Italy
Discover more than 139 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
139
experiences

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
September - October
Starting from
€700
Per person

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

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

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

5.0
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
€690
Per person

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

4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€280
Per person

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

4.8
Super!
Italy: Liguria
2 days - 2 nights
One departure available
August - September
€360
€324
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
2 departures available
September
€490
€441
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
4 departures available
August - September
Starting from
€490
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 - Sailboat yacht sailing holidays & tours in Italy
13644 reviews
Unforgettable adventure in the Aeolian Islands
08/27/2026
Daniele R.
-
IT
Amazing Pontine Islands on a sailing boat
08/27/2026
Rita G.
-
IT
Magical Pontine: full sail to discover the archipelago
08/27/2026
Enrico V.
-
IT
Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean
08/27/2026
Giangiacomo G.
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