
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.
468
experiences

4.8
Super!
Italy: Tuscany
2 days - 2 nights
6 departures available
July - October
Starting from
€230
Per person

4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
July
€410
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
July - August
€900
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
6 days - 6 nights
2 departures available
July - August
Starting from
€1,150
Per person

5.0
Super!
Greece: Sporades
7 days - 7 nights
One departure available
July - August
€890
€680
Per person

4.6
Italy: Tuscany
7 days - 6 nights
One departure available
August
€900
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€780
€693
Per person

5.0
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
€1,020
Per person

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

4.9
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
July - September
€400
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
7 days - 7 nights
4 departures available
August
€990
Per person

5.0
Super!
Italy: Tuscany
14 days - 14 nights
One departure available
August
€1,700
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
18079 reviews
Weekend at the Pontine Islands between Ponza and Palmarola
07/14/2026
Luca T.
-
IT
Long weekend among the queens of the archipelago - Elba and Capraia
07/14/2026
CHIARA A.
-
IT
Long weekend among the queens of the archipelago - Elba and Capraia
07/14/2026
Alessia B.
-
IT
Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company
07/14/2026
Luca S.
-
IT
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