
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.
302
experiences

4.7
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
€795
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
9 departures available
August - October
Starting from
€1,300
€1,040
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August - October
Starting from
€700
Per person

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August
€1,100
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€570
Per person

5.0
Super!
Italy: Liguria
2 days - 1 night
One departure available
October
€220
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
August - September
€950
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
8 departures available
August - October
Starting from
€570
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - October
€690
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€750
€675
Per person

5.0
Super!
France: Corsica
7 days - 6 nights
One departure available
August
€900
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
18462 reviews
Weekend Elba or Capraia
08/11/2026
Ilaria Maria Z.
-
IT
South Sardinia - A Marine Paradise to Explore!
08/11/2026
Giulia L.
-
IT
From Milos to Mykonos by sail, with skipper and on-board kitchen
08/11/2026
Anna M.
-
IT
Aeolian Islands: sun, sport, music, good food... The rest is magic!
08/11/2026
Mirella T.
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