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.
524
experiences
524
experiences
4.8
Italy: Pontine Islands
4 days - 3 nights
3 departures available
July - September
Starting from
€270
Per person
4.8
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
August
€600
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 7 nights
2 departures available
July
€790
Per person
4.6
Italy: Northern Sardinia
7 days - 6 nights
One departure available
August
€900
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
July - September
Starting from
€745
€671
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
2 departures available
August - September
Starting from
€955
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
8 departures available
July - September
Starting from
€600
Per person
5.0
Super!
France: French Riviera and Porquerolles
5 days - 4 nights
13 departures available
July - October
Starting from
€680
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
7 departures available
August - October
Starting from
€1,080
Per person
4.9
Super!
Italy: Venice and the Gulf of Trieste
1 day - 0 nights
One departure available
July
€100
Per person
5.0
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
August
€1,430
€1,287
Per person
4.8
Italy: Tuscany
6 days - 7 nights
3 departures available
August
Starting from
€900
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
16105 reviews
4 weekdays in the Pontine Islands
07/3/2025
Danilo S.
-
Italy
We have known the Aeolian Islands for 20 years, live them with us!
07/3/2025
Francesca S.
-
Italy
Four days in the Pontine archipelago
07/2/2025
Eleonora F.
-
Italy
Enjoy: in the blue painted blue of the Aeolian Islands
07/2/2025
Loris C.
-
Italy
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