
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.
176
experiences
5.0
New
France: French Riviera and Porquerolles
2 days - 2 nights
One departure available
September
€450
Per person

4.9
Greece: Sporades
6 days - 7 nights
2 departures available
September
Starting from
€750
Per person

4.7
Italy: Tuscany
2 days - 2 nights
One departure available
October
€180
Per person

5.0
Italy: Liguria
2 days - 2 nights
6 departures available
September - November
Starting from
€380
Per person

4.0
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,290
€1,161
Per person

4.4
Atlantic islands: Canary Islands
11 days - 11 nights
One departure available
October - November
€1,490
Per person

5.0
Italy: Liguria
2 days - 1 night
One departure available
October
€350
Per person

4.4
Atlantic islands: Canary Islands
10 days - 10 nights
One departure available
November
€890
Per person

4.5
Premium
Greece: Ionian Islands
7 days - 7 nights
3 departures available
September - October
Starting from
€845
€676
Per person - min 2 pax

4.8
Italy: Tuscany
3 days - 2 nights
3 departures available
September - October
€325
€309
Per person

4.9
France: French Riviera and Porquerolles
2 days - 1 night
6 departures available
September - November
€301
Per person

5.0
Croatia: Split Archipelago
7 days - 7 nights
4 departures available
September - October
Starting from
€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
19051 reviews
Egadi mon amour: seven days to fall in love, be amazed and relax.
09/7/2026
Monica Sofia S.
-
IT
A sailing story between Favignana, Levanzo and Marettimo
09/7/2026
DANIELA L.
-
IT
Unforgettable adventure in the Aeolian Islands
09/7/2026
Elisabetta M.
Sailing in the magical Sardinia of the South
09/7/2026
Elisa C.
-
IT
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