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.
594
experiences
594
experiences
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€180
Per person
Duration:
6 days - 7 nights
Croatia:
Split Archipelago
Give this experience a try!
Starting from
€518
€575
Per person
5.0
Duration:
6 days - 7 nights
Atlantic islands:
Canary Islands
Give this experience a try!
€725
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+8 travellers
have booked
Starting from
€523
€550
Per person
5.0
Duration:
6 days - 7 nights
Caribbean:
San Blas Islands - Panama
+14 travellers
have booked
€900
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Lake Maggiore
Give this experience a try!
€130
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+14 travellers
have booked
€99
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+6 travellers
have booked
Starting from
€100
Per person
Duration:
1 day - 1 night
Italy:
Liguria
Give this experience a try!
€120
Per person
Duration:
1 day - 0 nights
Italy:
Lazio
Give this experience a try!
€90
Per person
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
Give this experience a try!
Starting from
€500
Per person
5.0
Duration:
5 days - 4 nights
France:
French Riviera and Porquerolles
Starting from
€626
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
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