
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.
566
experiences

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

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
5 departures available
June - August
Starting from
€900
€765
Per person

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

5.0
Super!
Italy: Aeolian Islands
3 days - 2 nights
10 departures available
June - August
Starting from
€390
€351
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
July - August
Starting from
€850
€765
Per person

4.8
Italy: Tuscany
3 days - 3 nights
5 departures available
July - August
Starting from
€410
€369
Per person

4.6
Italy: Tuscany
7 days - 6 nights
2 departures available
July - August
Starting from
€800
Per person

4.7
Greece: Ionian Islands
6 days - 7 nights
One departure available
July - August
€1,052
Per person

4.5
Italy: Aeolian Islands
7 days - 7 nights
14 departures available
July - November
Starting from
€540
€513
Per person

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

4.9
Super!
France: French Riviera and Porquerolles
6 days - 7 nights
2 departures available
July - August
€800
Per person

4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
7 departures available
June - October
Starting from
€600
€540
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
17820 reviews
A week of sailing and sea life on the island of Elba
06/20/2026
Valentina P.
-
IT
A week sailing in the most beautiful places in the world
06/20/2026
Daniele M.
-
IT
"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
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