
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.
368
experiences

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
€700
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
August - October
Starting from
€750
€675
Per person

4.9
Italy: Tuscany
7 days - 6 nights
4 departures available
August - September
Starting from
€650
Per person

4.4
France: French Riviera and Porquerolles
6 days - 7 nights
6 departures available
August - September
Starting from
€730
€657
Per person

4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
August - September
Starting from
€600
€540
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€850
Per person

4.9
Super!
Italy: Tuscany
4 days - 3 nights
4 departures available
August - September
Starting from
€400
€360
Per person

5.0
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
€1,020
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
12 departures available
August - November
Starting from
€700
€665
Per person

4.9
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
August
Starting from
€250
Per person

4.4
Italy: Aeolian Islands
7 days - 7 nights
10 departures available
August - November
Starting from
€540
€513
Per person

5.0
Italy: Southern Sardinia
6 days - 7 nights
6 departures available
August - September
Starting from
€790
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
18272 reviews
Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera
08/1/2026
Fabrizio S.
-
IT
Capri Light Blue - Two boats in company!
08/1/2026
Maria bruna M.
-
IT
Two days at the Marine Protected Area of the Tremiti Islands
08/1/2026
Elisabetta M.
-
IT
North Sardinia and Corsica: blue seen from a sailboat
08/1/2026
Gabriele T.
-
IT
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