
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.
226
experiences

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
7 departures available
August - October
Starting from
€1,300
€780
Per person

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

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

4.7
Italy: Pontine Islands
3 days - 3 nights
One departure available
September
€420
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!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
October
€570
Per person

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

4.7
Italy: Tuscany
3 days - 3 nights
3 departures available
September
Starting from
€441
€419
Per person

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

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
Starting from
€585
€527
Per person

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

5.0
Super!
Italy: Pontine Islands
5 days - 4 nights
One departure available
September
€550
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
18895 reviews
A week in the Aeolian Islands - 6 islands in seven days
08/28/2026
Tiziana D.
7 days of sailing between beautiful Croatian islands and crystal clear waters
08/28/2026
Fabio F.
-
IT
10-Day Cruise to the Sporades & Nature Park
08/28/2026
Claudia G.
-
IT
Midweek on Elba, from Monday to Thursday
08/28/2026
Loriana V.
-
IT
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