Private yacht sailing holidays with skipper in Italy
Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.
362
experiences
362
experiences
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
10 travellers
Starting from
€1,219
€1,875
Per person
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
2 travellers
Starting from
€1,512
€1,890
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
51 travellers
€990
€1,190
Per person
5.0
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
€1,275
€1,500
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
28 travellers
Starting from
€667
€785
Per person
5.0
Super!
Duration:
4 days - 3 nights
Italy:
Tremiti Islands
4 travellers
€319
€375
Per person
4.5
Duration:
4 days - 4 nights
Italy:
Pontine Islands
Give this experience a try!
€378
€420
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
12 travellers
€419
€465
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
Starting from
€720
€800
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
€1,251
€1,390
Per person
4.7
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
Give this experience a try!
€621
€690
Per person
4.8
Duration:
3 days - 2 nights
Italy:
Tuscany
2 travellers
€234
€260
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
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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 - Private yacht sailing holidays with skipper in Italy
1272 reviews
Weekend of theoretical and practical course
03/11/2025
Domenico B.
-
Italy
Summer between the Tremiti and the Gargano
01/27/2025
Raffaele M.
-
Italy
On board with the chef at the Egadi Islands
01/23/2025
Alex P.
New Year's Eve 2024 on the Amalfi Coast - All inclusive
01/3/2025
Ilaria C.
-
Italy
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