
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.
128
experiences

4.8
Thailand: Phuket, Krabi and Phi Phi Islands
11 days - 11 nights
One departure available
December - January
€1,646
Per person

4.8
Atlantic islands: Canary Islands
6 days - 7 nights
10 departures available
January - December
Starting from
€900
Per person
4.1
Italy: Tuscany
2 days - 2 nights
31 departures available
January - December
Starting from
€275
€248
Per person
4.1
Italy: Tuscany
4 days - 4 nights
13 departures available
January - December
€1,400
Per person

4.4
Caribbean: Grenadines & Martinique
7 days - 7 nights
2 departures available
January
€950
€855
Per person

5.0
Thailand: Phuket, Krabi and Phi Phi Islands
7 days - 7 nights
11 departures available
February - December
Starting from
€1,500
€1,425
Per person

4.9
Italy: Liguria
1 day - 0 nights
9 departures available
July - August
€130
Per person

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

New
Caribbean: San Blas Islands - Panama
9 days - 9 nights
One departure available
December
€1,670
Per person

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

4.8
Greece: Cyclades
4 days - 4 nights
One departure available
April
€1,080
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
Feast of Santa Candida in Ventotene
11/9/2026
Gennaro A.
-
IT
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
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