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.
657
experiences
657
experiences
Duration:
2 days - 2 nights
Italy:
Liguria
+21 travellers
have booked
€380
Per person
4.9
Duration:
2 days - 1 night
Croatia:
Istrian peninsula
Give this experience a try!
Starting from
€230
Per person
4.9
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
+47 travellers
have booked
Starting from
€820
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Tuscany
+8 travellers
have booked
Starting from
€480
Per person
Duration:
7 days - 7 nights
Greece:
Sporades
Give this experience a try!
Starting from
€800
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Northern Sardinia
+13 travellers
have booked
Starting from
€1,390
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
Greece:
Dodecanese
Give this experience a try!
€550
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
+116 travellers
have booked
Starting from
€650
Per person
4.5
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+6 travellers
have booked
Starting from
€360
Per person
4.9
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
+50 travellers
have booked
Starting from
€499
€600
Per person
4.0
Duration:
7 days - 7 nights
Italy:
Pontine Islands
+7 travellers
have booked
Starting from
€600
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
14300 reviews
Let's discover the Aeolian Islands together by sailing
05/18/2024
Eros Giorgio M.
-
Italy
Weekend at the Pontine Islands: Ponza and Palmarola
05/18/2024
Giulio S.
-
Italy
In the blue of Capri and the infinity of the Amalfi Coast
05/15/2024
simona b.
An unforgettable sail to discover the Egadi Islands
05/14/2024
Marco B.
-
Switzerland
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