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.
569
experiences
569
experiences
Duration:
5 days - 5 nights
Greece:
Cyclades
Give this experience a try!
Starting from
€765
€900
Per person
4.5
Duration:
4 days - 3 nights
Italy:
Pontine Islands
Gennaro
€357
€420
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Pantelleria and Lampedusa
34 travellers
€595
€700
Per person
4.7
Duration:
6 days - 5 nights
Italy:
Tuscany
2 travellers
Starting from
€638
€750
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
30 travellers
Starting from
€667
€785
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Liguria
13 travellers
Starting from
€170
€200
Per person
Duration:
6 days - 5 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€850
€1,000
Per person
Duration:
5 days - 5 nights
Greece:
Cyclades
Give this experience a try!
Starting from
€765
€900
Per person
4.8
Super!
Duration:
7 days - 7 nights
Croatia:
Kornati Islands
28 travellers
€950
€1,100
Per person
4.9
Super!
Duration:
6 days - 7 nights
Greece:
Cyclades
4 travellers
€780
€890
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
18 travellers
Starting from
€342
€380
Per person
4.3
Duration:
6 days - 7 nights
Italy:
Northern Sardinia
4 travellers
Starting from
€720
€800
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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