
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.
97
experiences

4.5
Greece: Cyclades
5 days - 5 nights
3 departures available
May - October
€880
Per person

5.0
Atlantic islands: Canary Islands
7 days - 7 nights
One departure available
January
€850
Per person

5.0
France: Brittany and Normandy
4 days - 3 nights
11 departures available
July - September
Starting from
€500
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
24 departures available
May - October
Starting from
€550
Per person

5.0
Italy: Pontine Islands
4 days - 3 nights
11 departures available
June - September
Starting from
€450
Per person

5.0
Italy: Aeolian Islands
4 days - 4 nights
14 departures available
April - October
Starting from
€400
Per person

4.6
France: French Riviera and Porquerolles
7 days - 6 nights
16 departures available
June - September
Starting from
€620
Per person

5.0
France: Corsica
6 days - 7 nights
7 departures available
June - August
Starting from
€600
€570
Per person

4.3
Premium
Croatia: Kornati Islands
7 days - 7 nights
18 departures available
May - October
Starting from
€905
€815
Per person - min 2 pax

5.0
Greece: Ionian Islands
6 days - 6 nights
3 departures available
January - December
€500
Per person

Italy: Tuscany
1 day - 0 nights
One departure available
November
€135
Per person

4.8
Greece: Ionian Islands
7 days - 7 nights
16 departures available
June - September
Starting from
€600
€540
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
17615 reviews
Squid Festival: let's close the season on a high note! - on board a 17mt boat
11/5/2025
Marco F.
-
Switzerland
LET'S GO TO TOTANI - Festival in Capria
11/5/2025
Marco D.
-
Italy
IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper and skipper and travel insurance
11/3/2025
Patrizia M.
-
Italy
End of season weekend in the Aeolian Islands
11/3/2025
Collwyn Y.
-
Italy
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