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.
652
experiences
652
experiences
Duration:
4 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€396
€440
Per person
4.9
Duration:
4 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€300
Per person
4.5
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Gennaro A.
has booked
€328
€345
Per person
5.0
Duration:
4 days - 3 nights
Italy:
Gulf of Naples
Give this experience a try!
€380
Per person
4.7
Duration:
3 days - 3 nights
Italy:
Gulf of Naples
Give this experience a try!
€320
Per person
5.0
Duration:
6 days - 5 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€580
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Tuscany
+2 travellers
have booked
€280
Per person
4.9
Duration:
2 days - 2 nights
Croatia:
Istrian peninsula
Alberto B.
has booked
Starting from
€190
Per person
5.0
Duration:
2 days - 1 night
France:
Brittany and Normandy
Give this experience a try!
€250
Per person
5.0
Duration:
2 days - 1 night
France:
French Riviera and Porquerolles
+4 travellers
have booked
Starting from
€287
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+38 travellers
have booked
Starting from
€99
Per person
Duration:
6 days - 6 nights
Greece:
Dodecanese
Give this experience a try!
€1,450
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
14261 reviews
Luxury sailing in the Gulf of Poets
04/15/2024
Antonio C.
-
Italy
Sailing Cyclades
04/15/2024
yannis b.
-
France
Thailand and the Andaman Sea
04/13/2024
Paola S.
-
Italy
Veleggiata verso il farò di Cecina con Aperitivo a bordo
04/11/2024
maurizio r.
-
Italy
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