
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.
641
experiences

4.6
Italy: Pontine Islands
3 days - 2 nights
5 departures available
May - June
Starting from
€250
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
2 departures available
June - July
Starting from
€440
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
3 departures available
May - September
Starting from
€700
€630
Per person

4.7
Italy: Tuscany
6 days - 7 nights
2 departures available
July - August
Starting from
€999
€949
Per person

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

4.8
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
August - September
€950
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
May - June
€420
Per person

5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
2 departures available
September
€900
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
2 departures available
September
€750
€675
Per person
5.0
Italy: Tuscany
3 days - 2 nights
3 departures available
July - September
Starting from
€230
Per person

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
9 departures available
June - August
Starting from
€850
Per person

5.0
Italy: Tuscany
3 days - 3 nights
3 departures available
June - September
Starting from
€350
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
17663 reviews
Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola
05/12/2026
Paola A.
-
Italy
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
05/11/2026
Lucia K.
-
Switzerland
May Day between Elba and Capraia
05/11/2026
Valeria C.
-
Italy
Relaxing weekend in the Pontine Islands
05/11/2026
Flavia F.
-
Italy
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