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.
545
experiences
545
experiences
5.0
Duration:
1 day - 1 night
Italy:
Liguria
Give this experience a try!
Starting from
€119
Per person
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
Starting from
€110
Per person
4.9
Duration:
3 days - 4 nights
Spain:
Galicia
Give this experience a try!
€150
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€280
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€390
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
+3 travellers
have booked
€314
€330
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€314
€330
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+3 travellers
have booked
Starting from
€250
Per person
4.6
Duration:
2 days - 2 nights
Italy:
Tuscany
+8 travellers
have booked
Starting from
€180
Per person
5.0
Duration:
2 days - 2 nights
Spain:
The Balearic Islands
+14 travellers
have booked
Starting from
€200
€210
Per person
Duration:
2 days - 2 nights
Italy:
Liguria
Give this experience a try!
€200
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
Claudia D.
has booked
Starting from
€224
€249
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
14252 reviews
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
Sailing course in the Cyclades
10/18/2023
Antoine B.
-
Belgium
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & SupportLet's talk Sailsquare!
Sailsquare
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964