
Sailboat holidays & skippered tours
The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.
154
experiences

4.1
Italy: Aeolian Islands
6 days - 7 nights
One departure available
September - October
€680
Per person

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

4.8
Italy: Tuscany
3 days - 2 nights
3 departures available
September - October
€325
€309
Per person

4.9
Greece: Sporades
6 days - 7 nights
2 departures available
September
Starting from
€750
Per person

5.0
Italy: Liguria
2 days - 2 nights
6 departures available
September - November
Starting from
€380
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
5 departures available
September - October
Starting from
€585
€527
Per person

4.6
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
Starting from
€700
€630
Per person

4.7
Italy: Tuscany
2 days - 2 nights
One departure available
October
€180
Per person

4.0
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,290
Per person

5.0
Italy: Liguria
2 days - 1 night
One departure available
October
€350
Per person

4.4
Atlantic islands: Canary Islands
10 days - 10 nights
One departure available
November
€890
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 holidays & skippered tours
19108 reviews
Unforgettable adventure in the Aeolian Islands
09/12/2026
Andrea M.
Midweek getaway between Elba and Capraia
09/12/2026
Nikhita R.
-
IT
Midweek relaxing in the Pontine Islands
09/12/2026
Giovanni F.
-
IT
Summer 2026 - Catamaran week in the Pontine Islands
09/12/2026
Maverick R.
-
IT
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