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.
675
experiences
675
experiences
5.0
Duration:
1 day - 0 nights
Italy:
Tuscany
Give this experience a try!
€130
Per person
4.4
Duration:
1 day - 0 nights
Italy:
Northern Sardinia
Give this experience a try!
€90
Per person
4.6
Duration:
9 days - 9 nights
Greece:
Peloponnese
+3 travellers
have booked
€980
Per person
5.0
Duration:
3 days - 4 nights
Italy:
Aegadian islands
+17 travellers
have booked
Starting from
€400
Per person
4.6
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€400
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Tuscany
+29 travellers
have booked
€320
Per person
4.3
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€499
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Pontine Islands
+3 travellers
have booked
Starting from
€360
Per person
4.8
Duration:
3 days - 3 nights
Italy:
Tuscany
+2 travellers
have booked
Starting from
€324
€360
Per person
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€270
Per person
4.5
Duration:
4 days - 3 nights
France:
French Riviera and Porquerolles
+3 travellers
have booked
€440
Per person
5.0
Duration:
4 days - 3 nights
Italy:
Venice and the Gulf of Trieste
Give this experience a try!
€279
€310
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
14307 reviews
Weekend of sea and colors between Ischia, Procida and Vivara
05/21/2024
Juri R.
-
Germany
The fantastic Saronic Islands and the surroundings of Athens
05/21/2024
Steve T.
-
Canada
Sailing course on the Côte d'Azur aboard a 15-metre sailboat
05/21/2024
Marie-Albane r.
-
France
Weekend of sea and colors between Ischia, Procida and Vivara
05/21/2024
Annalisa S.
-
Italy
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