
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.
347
experiences

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€713
Per person

4.5
Spain: The Balearic Islands
6 days - 6 nights
2 departures available
August - September
Starting from
€1,010
Per person

5.0
Super!
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

5.0
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
September
€650
Per person

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

5.0
Super!
France: Corsica
7 days - 7 nights
One departure available
August
€1,050
Per person

4.8
Super!
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August
€990
Per person

5.0
Italy: Southern Sardinia
6 days - 7 nights
6 departures available
August - September
Starting from
€790
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€990
Per person

4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
4 departures available
August - September
Starting from
€716
Per person

5.0
New
France: Corsica
7 days - 6 nights
One departure available
August
€900
Per person

5.0
Super!
France: Corsica
3 days - 3 nights
One departure available
August
€290
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
18347 reviews
La Maddalena Archipelago and South Corsica
08/4/2026
Laura D.
-
IT
Sailing in Tigullio: Half-Day Experience from Rapallo
08/4/2026
Barbara P.
-
IT
Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK
08/4/2026
Lucia S.
-
IT
Gulf of Poets and Cinque Terre
08/4/2026
Veronica B.
-
IT
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