
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.
184
experiences

4.9
Greece: Cyclades
7 days - 7 nights
3 departures available
October
Starting from
€950
Per person

4.8
Italy: Tuscany
3 days - 3 nights
One departure available
September
€380
Per person

4.7
Italy: Pontine Islands
3 days - 2 nights
2 departures available
September
Starting from
€312
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
6 departures available
September - October
Starting from
€585
€527
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
Starting from
€300
€270
Per person

4.6
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person
5.0
New
France: French Riviera and Porquerolles
2 days - 2 nights
One departure available
September
€450
Per person

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

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

4.7
Italy: Tuscany
7 days - 6 nights
3 departures available
September
€700
Per person

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

4.0
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,290
€1,161
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
19025 reviews
Four nights in the Pontine Islands - midweek
09/5/2026
Angela Chiara C.
-
IT
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
09/5/2026
Paolo F.
-
IT
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
09/5/2026
Aurelio C.
-
IT
Tuscany and Corsica: sailing sun adventure good food energy and well-being
09/5/2026
Valentina R.
-
IT
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