
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.
504
experiences

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
9 departures available
July - October
Starting from
€570
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
August - October
Starting from
€690
Per person

4.7
Italy: Tuscany
6 days - 6 nights
2 departures available
August - September
Starting from
€1,041
Per person

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

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€1,100
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
13 departures available
July - October
Starting from
€570
Per person

4.7
Italy: Tuscany
6 days - 7 nights
2 departures available
July - August
Starting from
€1,052
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
4 departures available
August - September
Starting from
€950
Per person

4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
August
€800
Per person

4.4
France: French Riviera and Porquerolles
6 days - 7 nights
9 departures available
July - September
Starting from
€730
€657
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€650
€585
Per person

5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
7 departures available
August - September
Starting from
€790
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
17998 reviews
Corfu between bays, taverns and myths.
07/8/2026
Farida B.
-
IT
Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company
07/8/2026
Fabio C.
-
IT
Long weekend between Ponza and Palmarola: adventure at the Pontine!
07/8/2026
ELISABETTA P.
-
IT
Sailing in the magical Sardinia of the South
07/8/2026
Cristina B.
-
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