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.
598
experiences
598
experiences
5.0
Duration:
4 days - 4 nights
Italy:
Gulf of Naples
Give this experience a try!
€350
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€380
Per person
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
Starting from
€110
Per person
4.9
Duration:
5 days - 4 nights
Italy:
Aegadian islands
Give this experience a try!
Starting from
€450
Per person
Duration:
5 days - 4 nights
Italy:
Pontine Islands
Give this experience a try!
€350
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Tuscany
+2 travellers
have booked
€280
Per person
4.0
Duration:
4 days - 3 nights
Italy:
Southern Sardinia
Give this experience a try!
€400
Per person
4.9
Duration:
4 days - 5 nights
Spain:
Galicia
Give this experience a try!
€399
Per person
4.3
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€440
Per person
4.3
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€600
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€180
Per person
5.0
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€300
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
14253 reviews
A weekend of sailing between Capraia and the island of Elba
03/20/2024
davide C.
-
Italy
Guadeloupe and its islands in ten days
02/10/2024
Caterina P.
-
Italy
Guadeloupe and its islands in ten days
02/9/2024
Franck P.
-
France
Guadeloupe and its islands in ten days
02/8/2024
Lucie C.
-
France
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