
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.
116
experiences

4.5
France: Corsica
7 days - 7 nights
4 departures available
July - August
Starting from
€1,000
Per person

4.8
Thailand: Phuket, Krabi and Phi Phi Islands
14 days - 14 nights
One departure available
January
€2,100
Per person

4.9
Greece: Sporades
6 days - 6 nights
19 departures available
May - September
Starting from
€700
Per person

4.4
Caribbean: Guadeloupe
10 days - 10 nights
One departure available
February
€1,250
Per person

4.7
Italy: Tuscany
7 days - 6 nights
11 departures available
June - August
Starting from
€660
Per person
4.9
Italy: Pontine Islands
6 days - 6 nights
4 departures available
July - August
Starting from
€1,037
Per person

5.0
Spain: The Balearic Islands
6 days - 6 nights
14 departures available
June - September
Starting from
€1,132
€906
Per person

4.2
Italy: Aeolian Islands
6 days - 7 nights
20 departures available
May - October
Starting from
€780
Per person

4.8
Italy: Pontine Islands
7 days - 7 nights
6 departures available
July - September
Starting from
€962
€866
Per person

5.0
New
France: French Riviera and Porquerolles
5 days - 4 nights
27 departures available
February - October
Starting from
€595
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
18 departures available
June - October
Starting from
€690
Per person

5.0
Croatia: Istrian peninsula
7 days - 7 nights
5 departures available
May - June
€1,100
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
19291 reviews
It's time for sun and sea!
11/5/2026
francesca t.
-
IT
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
11/3/2026
Alvise V.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
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