
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.
629
experiences

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
15 departures available
June - October
Starting from
€689
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
16 departures available
May - October
Starting from
€540
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
16 departures available
May - October
Starting from
€650
€585
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
12 departures available
June - September
Starting from
€600
€540
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
23 departures available
May - November
Starting from
€650
€618
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
7 departures available
May - July
Starting from
€370
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
7 departures available
May - July
Starting from
€650
€585
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
21 departures available
May - October
Starting from
€590
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€680
Per person

4.8
Super!
Greece: Cyclades
7 days - 7 nights
2 departures available
August
€990
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
12 departures available
May - September
Starting from
€1,000
€890
Per person

5.0
Super!
Greece: Sporades
7 days - 7 nights
6 departures available
July - September
Starting from
€650
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
17638 reviews
May Day between Elba and Capraia
05/3/2026
Jennifer G.
-
Italy
Weekend sailing course from Bandol
05/2/2026
Nathalie R.
-
France
4 Days Exploring the Chausey Islands from Saint-Malo
04/30/2026
Claire M.
-
France
Sailing cruise in the Greek islands - The Saronic Islands
04/29/2026
Marc G.
-
Canada
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