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.
630
experiences
630
experiences
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€90
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€275
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€250
Per person
4.7
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
Starting from
€260
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
+9 travellers
have booked
Starting from
€250
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+8 travellers
have booked
Starting from
€239
€265
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
+13 travellers
have booked
Starting from
€237
€249
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+34 travellers
have booked
Starting from
€228
€240
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Lake Maggiore
Give this experience a try!
€181
€190
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
+15 travellers
have booked
Starting from
€260
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
cosetta
has booked
€265
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Liguria
+2 travellers
have booked
€275
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
14264 reviews
A weekend of sailing between Capraia and the island of Elba
04/24/2024
Angelo C.
-
Italy
Easter on the Island of Elba
04/22/2024
Antonios S.
-
Italy
Trekking and sailing weekend on the island of Elba
04/22/2024
Sara C.
-
Italy
Luxury sailing in the Gulf of Poets
04/15/2024
Antonio C.
-
Italy
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