
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.
605
experiences

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

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

4.9
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
July
€420
Per person

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

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

5.0
Super!
Italy: Southern Sardinia
4 days - 3 nights
4 departures available
June - September
€740
Per person

4.8
Italy: Naples & Amalfi Coast
7 days - 7 nights
One departure available
August
€977
€879
Per person

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

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

5.0
Super!
Italy: Tuscany
6 days - 6 nights
2 departures available
August
Starting from
€849
Per person

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

5.0
Super!
Italy: Tuscany
7 days - 7 nights
2 departures available
August
Starting from
€1,060
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
17765 reviews
Three-Day Sailing Tour to the Pontine Islands
06/13/2026
Giorgio T.
-
IT
Magical Bridge to the Pontine Islands
06/12/2026
Federica G.
-
IT
Summer is made for the Aeolian Islands! Weekly cruise
06/11/2026
Patrizia R.
-
IT
June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide
06/10/2026
Guido F.
-
IT
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