
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.
553
experiences

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
6 departures available
July - October
Starting from
€420
€399
Per person

5.0
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
August
€1,060
Per person

4.8
Italy: Naples & Amalfi Coast
3 days - 2 nights
2 departures available
September - October
€242
€218
Per person

5.0
New
Italy: Aegadian islands
7 days - 7 nights
7 departures available
June - September
Starting from
€600
€540
Per person

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

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

4.8
Super!
Italy: Pontine Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€900
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
8 departures available
July - September
€1,600
Per person

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

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€410
Per person

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

5.0
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
September - November
€250
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
17855 reviews
Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!
06/23/2026
Kim W.
-
CA
Amazing Pontine Islands on a sailboat with private bathrooms
06/23/2026
Giulia C.
-
IT
Weekend Elba or Capraia
06/23/2026
Andrea B.
-
IT
Weekend at the Pontine Islands between Ponza and Palmarola
06/23/2026
sophia jasmine t.
-
IT
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