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.
58
experiences
58
experiences
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
25 departures available
May - October
Starting from
€600
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€625
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
October - November
€583
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
21 departures available
May - October
Starting from
€950
Per person
4.6
Italy: Tuscany
3 days - 2 nights
One departure available
October
€200
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
October - November
€320
Per person
4.9
Super!
Italy: Liguria
2 days - 2 nights
One departure available
June
€360
Per person
4.9
Super!
Italy: Tuscany
4 days - 3 nights
16 departures available
May - September
Starting from
€430
€409
Per person
4.9
Super!
Italy: Tuscany
7 days - 7 nights
9 departures available
July - September
Starting from
€700
Per person
4.8
Super!
Italy: Pontine Islands
4 days - 3 nights
17 departures available
April - July
Starting from
€210
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
One departure available
October
€1,325
Per person
4.8
Italy: Tuscany
2 days - 2 nights
One departure available
October
€300
Per person
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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
2576 reviews
Fantastic BARCOLANA: Racing in safety and joy!
10/15/2025
Giulia B.
-
Italy
Barcolana weekend in Trieste and surroundings.
10/15/2025
Barbara M.
-
Italy
Weekend in Capraia, the island with timeless sunsets
10/14/2025
Gloria G.
-
Italy
Barcolana 2025: experience the most beautiful regatta with me!
10/14/2025
Gabriele I.
-
Italy
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