
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.
408
experiences

5.0
Italy: Aeolian Islands
3 days - 2 nights
3 departures available
July - August
Starting from
€390
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
4 departures available
August - October
€650
Per person

5.0
Super!
Croatia: Istrian peninsula
7 days - 7 nights
2 departures available
August
€649
Per person

5.0
Super!
France: French Riviera and Porquerolles
8 days - 7 nights
One departure available
August
€750
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
September
€200
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€690
€613
Per person

4.7
Italy: Liguria
6 days - 6 nights
One departure available
July - August
€946
Per person

5.0
Super!
Greece: Sporades
7 days - 7 nights
One departure available
July - August
€890
€680
Per person

4.8
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
July - August
€900
Per person

4.8
Super!
Italy: Tuscany
7 days - 6 nights
One departure available
August
€890
Per person

4.7
Croatia: Kornati Islands
6 days - 7 nights
3 departures available
August
Starting from
€800
€760
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€920
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
18154 reviews
Weekend among the most beautiful coves of Elba
07/21/2026
marco c.
-
IT
Sailing holiday in the turquoise blue waters of Corsica
07/21/2026
Laura P.
-
IT
Long weekend in the Pontine Islands between Ponza and Palmarola
07/21/2026
Valeria T.
-
IT
Weekend on a Sailing Boat in the Magical Gulf of Poets
07/21/2026
Novella C.
-
IT
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