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.
632
experiences
632
experiences
4.6
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Give this experience a try!
€360
€400
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Tuscany
+21 travellers
have booked
Starting from
€304
€320
Per person
Duration:
3 days - 2 nights
Italy:
Aeolian Islands
Give this experience a try!
Starting from
€290
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
5.0
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
Starting from
€313
Per person
4.6
Duration:
2 days - 2 nights
Italy:
Tuscany
+8 travellers
have booked
€200
Per person
4.6
Duration:
2 days - 2 nights
Italy:
Liguria
+10 travellers
have booked
€290
Per person
5.0
Duration:
7 days - 8 nights
Italy:
Tuscany
Philip J.
has booked
€500
Per person
5.0
Duration:
2 days - 1 night
France:
Brittany and Normandy
Give this experience a try!
Starting from
€150
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+7 travellers
have booked
€105
Per person
5.0
Duration:
7 days - 6 nights
France:
French Riviera and Porquerolles
Give this experience a try!
Starting from
€790
Per person
Duration:
3 days - 2 nights
Italy:
Sicily
Give this experience a try!
Starting from
€801
€890
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
14278 reviews
1st May - Whale watching cruise with WWF researcher between Elba and Capraia
05/6/2024
Elettra B.
-
Italy
1st May - Whale watching cruise with WWF researcher between Elba and Capraia
05/6/2024
Francesca S.
-
Italy
April 25th long weekend in Bastia
05/6/2024
Lisa V.
-
Italy
25 April - 4 days sailing between La Maddalena and Bonifacio
05/3/2024
Bart S.
-
Spain
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