Sailboat yacht sailing holidays & tours in Italy
Discover more than 296 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
296
experiences
296
experiences
4.6
Italy: Pontine Islands
7 days - 7 nights
5 departures available
July - September
Starting from
€719
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - September
Starting from
€650
Per person
5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
3 departures available
July - August
Starting from
€900
€810
Per person
4.8
Super!
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,190
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
August - October
Starting from
€200
Per person
5.0
Super!
Italy: Tuscany
6 days - 7 nights
2 departures available
August - September
Starting from
€793
€714
Per person
4.7
Italy: Northern Sardinia
6 days - 7 nights
9 departures available
July - September
Starting from
€650
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
7 departures available
July - September
Starting from
€690
€621
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
July - August
Starting from
€780
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€935
€748
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
8 days - 7 nights
4 departures available
July - September
Starting from
€660
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
9 departures available
August - November
Starting from
€530
€477
Per person
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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 - Sailboat yacht sailing holidays & tours in Italy
11459 reviews
Short sailing cruise in the Gulf of Naples
07/5/2025
francesca s.
-
Italy
Un giorno intero in barca a vela nel golfo di ALASSIO
07/5/2025
Aaron C.
-
Italy
All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento
07/5/2025
MANJA B.
-
Slovenia
Life-changing experiences: Four days in the Pontine Islands
07/5/2025
Massimo M.
-
Italy
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