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.
577
experiences
577
experiences
Duration:
7 days - 7 nights
Greece:
Cyclades
Give this experience a try!
Starting from
€798
€997
Per person
Duration:
7 days - 7 nights
Greece:
Cyclades
8 travellers
Starting from
€736
€920
Per person
4.7
Duration:
6 days - 7 nights
Spain:
The Balearic Islands
37 travellers
Starting from
€960
€1,200
Per person
5.0
Duration:
6 days - 5 nights
North Sea:
Norway
Give this experience a try!
€480
€600
Per person
5.0
Duration:
6 days - 5 nights
North Sea:
Norway
Give this experience a try!
€480
€600
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
62 travellers
€990
€1,190
Per person
5.0
Super!
Duration:
4 days - 4 nights
Italy:
Tuscany
Give this experience a try!
€380
€460
Per person
5.0
Super!
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€1,275
€1,500
Per person
5.0
Super!
Duration:
6 days - 6 nights
Spain:
The Balearic Islands
12 travellers
Starting from
€765
€900
Per person
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€353
€415
Per person
Duration:
5 days - 5 nights
Greece:
Cyclades
Give this experience a try!
Starting from
€765
€900
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Pantelleria and Lampedusa
34 travellers
€595
€700
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
15813 reviews
First spring getaways in the company of the sea
04/29/2025
Raffaella Valeria R.
-
Italy
From Sanremo sailing holiday to discover the Côte d'Azur
04/29/2025
Alessandra V.
-
Italy
25 April long weekend between Capraia and Northern Corsica
04/29/2025
VERONICA D.
-
Italy
Day trip with aperitif at sunset!
04/28/2025
Silvia Maddalena V.
-
Italy
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