
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.
601
experiences

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
13 departures available
June - October
Starting from
€570
Per person

4.9
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
August
€890
Per person

4.6
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€490
Per person
4.7
Italy: Tuscany
2 days - 2 nights
39 departures available
January - December
Starting from
€300
€270
Per person

4.7
Italy: Tuscany
6 days - 6 nights
5 departures available
June - September
Starting from
€999
€949
Per person

4.6
Greece: Ionian Islands
7 days - 7 nights
2 departures available
August
Starting from
€874
€699
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
6 departures available
June - September
Starting from
€650
€585
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - October
Starting from
€650
€585
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
3 departures available
June - July
Starting from
€290
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
9 departures available
June - September
Starting from
€490
€466
Per person

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

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
7 departures available
June - October
Starting from
€420
€399
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
17720 reviews
Pontine Islands in 4 days: sailing, caves and crystal clear waters
06/4/2026
Matteo B.
-
IT
Long weekend of June 2nd on the Costa Smeralda
06/4/2026
Silvia B.
-
IT
June 2nd long weekend: discovering Capri, Ischia and Procida
06/4/2026
Ivana G.
-
IT
June 2 long weekend between Capraia and Corsica - 2 boats
06/4/2026
Rebecca C.
-
IT
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