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.
570
experiences
570
experiences
Duration:
7 days - 7 nights
Greece:
Cyclades
2 travellers
€788
€876
Per person
4.9
Duration:
6 days - 6 nights
Italy:
Aegadian islands
2 travellers
€531
€590
Per person
Duration:
7 days - 7 nights
Italy:
Pontine Islands
14 travellers
Starting from
€1,080
€1,200
Per person
4.7
Duration:
6 days - 6 nights
Italy:
Northern Sardinia
Give this experience a try!
€774
€860
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Southern Sardinia
12 travellers
€612
€680
Per person
4.7
Duration:
6 days - 7 nights
Turkey:
Turkey
3 travellers
€648
€720
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
23 travellers
Starting from
€356
€395
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
€720
€800
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
2 travellers
€810
€900
Per person
4.3
Duration:
7 days - 7 nights
France:
French Riviera and Porquerolles
48 travellers
Starting from
€585
€650
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€405
€450
Per person
5.0
Super!
Duration:
6 days - 6 nights
Spain:
The Balearic Islands
94 travellers
Starting from
€711
€790
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
15833 reviews
Sailing course on the Côte d'Azur aboard a 15-metre sailboat
05/9/2025
Caroline T.
-
France
1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK
05/8/2025
Maria Pia D.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
05/7/2025
Janette G.
-
Australia
A long weekend of sea and freedom from Argentario to Elba
05/7/2025
RAFFAELE L.
-
Italy
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