
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.
569
experiences

5.0
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
September - November
€250
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
Per person

New
Italy: Pantelleria and Lampedusa
7 days - 7 nights
10 departures available
July - November
Starting from
€500
€425
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
July - September
Starting from
€690
€621
Per person

5.0
Super!
Italy: Pontine Islands
7 days - 7 nights
3 departures available
August
€650
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
8 departures available
August - October
€650
Per person

4.9
Super!
Croatia: Istrian peninsula
3 days - 2 nights
6 departures available
July - October
€260
Per person

4.8
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
July
€590
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
July - September
Starting from
€200
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
14 departures available
July - November
Starting from
€600
€540
Per person

5.0
Italy: Aegadian islands
7 days - 7 nights
10 departures available
June - September
Starting from
€700
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
7 days - 7 nights
4 departures available
August
€990
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
17818 reviews
"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene
06/20/2026
Fabio F.
-
IT
Long weekend on a sailing boat between Capraia and Corsica
06/20/2026
Mattia V.
-
IT
Midweek relaxing in the Pontine Islands
06/20/2026
MARINA C.
-
IT
4 weekdays in the Pontine Islands
06/20/2026
simona s.
-
IT
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