
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.
180
experiences
5.0
Super!
Greece: Cyclades
6 days - 6 nights
2 departures available
September
Starting from
€1,000
€750
Per person

4.9
Super!
North Sea: Norway
7 days - 7 nights
One departure available
October
€1,200
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September - October
€835
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€980
Per person

4.9
Italy: Aeolian Islands
3 days - 2 nights
7 departures available
September - October
€320
Per person

5.0
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€350
Per person

4.3
New
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
September - October
€890
Per person

4.1
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
September - October
Starting from
€680
Per person

4.7
Italy: Pontine Islands
3 days - 2 nights
2 departures available
September
Starting from
€312
Per person

4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€3,900
Per person

4.8
Italy: Aegadian islands
6 days - 7 nights
One departure available
September - October
€600
Per person

4.8
Italy: Southern Sardinia
6 days - 7 nights
One departure available
September
€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
19039 reviews
Aeolian Islands on a luxury sailing boat
09/6/2026
Palma A.
-
IT
Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters
09/6/2026
Orazio F.
-
IT
The Island of Elba, to make you live a special experience!
09/6/2026
Andrea C.
-
IT
A week in the Aeolian Islands - 6 islands in seven days
09/6/2026
Giorgia Z.
-
IT
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