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.
652
experiences
652
experiences
4.4
Duration:
1 day - 0 nights
Italy:
Northern Sardinia
Give this experience a try!
€90
Per person
4.7
Duration:
4 days - 4 nights
Italy:
Liguria
Give this experience a try!
€590
Per person
5.0
Duration:
4 days - 3 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€500
Per person
5.0
Duration:
4 days - 4 nights
Italy:
Gulf of Naples
Give this experience a try!
€300
Per person
Duration:
5 days - 4 nights
Italy:
Pontine Islands
Give this experience a try!
€350
Per person
5.0
Duration:
4 days - 4 nights
Italy:
Liguria
+2 travellers
have booked
€450
Per person
4.3
Duration:
4 days - 4 nights
France:
French Riviera and Porquerolles
Give this experience a try!
€414
€460
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Gulf of Naples
Give this experience a try!
€160
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Venice and the Gulf of Trieste
+4 travellers
have booked
Starting from
€95
Per person
5.0
Duration:
4 days - 3 nights
Italy:
Tuscany
+3 travellers
have booked
€470
Per person
4.8
Duration:
3 days - 4 nights
Italy:
Aegadian islands
+17 travellers
have booked
€350
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
Give this experience a try!
Starting from
€324
€360
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
14261 reviews
Luxury sailing in the Gulf of Poets
04/15/2024
Antonio C.
-
Italy
Sailing Cyclades
04/15/2024
yannis b.
-
France
Thailand and the Andaman Sea
04/13/2024
Paola S.
-
Italy
Veleggiata verso il farò di Cecina con Aperitivo a bordo
04/11/2024
maurizio r.
-
Italy
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