
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.
299
experiences

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
Per person

4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€280
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
€585
€527
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
August - September
Starting from
€600
€540
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
€300
€270
Per person

4.8
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
August - September
Starting from
€360
€300
Per person

4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
August - September
Starting from
€600
€540
Per person

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

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
September
€950
Per person

5.0
Super!
Italy: Pontine Islands
5 days - 4 nights
One departure available
September
€600
Per person

4.9
Italy: Aeolian Islands
6 days - 7 nights
One departure available
September
€583
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
4 departures available
August - September
Starting from
€700
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
18474 reviews
Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea
08/12/2026
Eleonora B.
-
IT
Midweek sailing trip: two days at sea in Alassio
08/12/2026
Stephanie M.
-
IT
The Mediterranean Mini-Flotilla: Capri, Ischia, and the Pontine Islands
08/12/2026
Alessandra P.
-
IT
Amazing Pontine Islands on a sailing boat
08/12/2026
Fabia D.
-
IT
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