
Sailboat yacht sailing holidays & tours in Italy
Discover more than 300 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
300
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
8 departures available
July - September
Starting from
€700
Per person

4.8
Italy: Northern Sardinia
6 days - 7 nights
11 departures available
July - October
Starting from
€590
Per person

4.6
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
Starting from
€1,260
€1,070
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
8 departures available
July - September
Starting from
€600
€570
Per person

4.7
Italy: Naples & Amalfi Coast
3 days - 3 nights
One departure available
July
€390
Per person

4.7
Italy: Pontine Islands
7 days - 7 nights
4 departures available
July - September
Starting from
€795
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
2 departures available
August - September
€1,150
€1,035
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
August - October
Starting from
€690
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
6 departures available
July - September
Starting from
€900
Per person

4.7
Italy: Tuscany
6 days - 6 nights
2 departures available
August - September
Starting from
€1,041
Per person
4.1
Italy: Tuscany
2 days - 2 nights
33 departures available
January - December
Starting from
€300
€270
Per person

4.7
Italy: Tuscany
6 days - 7 nights
2 departures available
July - August
Starting from
€1,052
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
12937 reviews
All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento
07/2/2026
Luigi C.
-
IT
Mini-cruise with WWF guide in the heart of the Tuscan Archipelago
07/2/2026
Bianca Matelda C.
-
IT
Weekend on the island of Elba: among dolphins, enchanting bays and relaxation
07/2/2026
Laura N.
-
IT
Four days in the Pontine Islands, just a stone's throw from Rome
07/1/2026
Stefano A.
-
IT
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