
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.
124
experiences

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
Italy: Liguria
2 days - 1 night
One departure available
October
€290
Per person

5.0
Croatia: Istrian peninsula
7 days - 7 nights
5 departures available
May - June
€1,100
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
One departure available
October
€600
Per person

4.4
France: Corsica
6 days - 7 nights
5 departures available
July - August
Starting from
€750
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
June
€625
Per person

5.0
New
Italy: Northern Sardinia
7 days - 7 nights
One departure available
September
€620
€590
Per person

4.2
Italy: Southern Sardinia
6 days - 7 nights
2 departures available
August
Starting from
€896
€806
Per person
4.6
Italy: Aeolian Islands
6 days - 6 nights
18 departures available
May - September
Starting from
€600
€540
Per person

4.4
Caribbean: BVI - British Virgin Islands
10 days - 10 nights
One departure available
March
€1,350
€1,147
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
19280 reviews
Barcolana 58: a day at the most famous regatta in the world
10/18/2026
Laura P.
-
IT
Sailing in the Cyclades
10/18/2026
Tanya S.
-
GR
IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper
10/17/2026
Elena V.
Learn to sail in Liguria: First level sailing course
10/17/2026
Nicole C.
-
IT
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