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.
631
experiences
631
experiences
4.9
Duration:
3 days - 2 nights
Italy:
Tuscany
+4 travellers
have booked
Starting from
€240
Per person
4.9
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€400
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+3 travellers
have booked
€240
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+15 travellers
have booked
Starting from
€269
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+33 travellers
have booked
Starting from
€230
Per person
4.5
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+5 travellers
have booked
Starting from
€269
Per person
4.8
Duration:
3 days - 2 nights
Italy:
Amalfi Coast
+18 travellers
have booked
€450
Per person
Duration:
3 days - 2 nights
Italy:
Aeolian Islands
Give this experience a try!
Starting from
€219
€230
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€275
Per person
4.6
Duration:
2 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€200
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+30 travellers
have booked
Starting from
€248
€275
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€90
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
14275 reviews
25 April - 4 days sailing between La Maddalena and Bonifacio
05/3/2024
Bart S.
-
Spain
Sailing, early sun and aperitif at sunset ... What else?
05/3/2024
Cristiana L.
-
Italy
May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms
05/2/2024
susanna s.
-
Italy
25 April - Whale watching expedition with WWF researcher in Liguria
05/2/2024
Rossella D.
-
Italy
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