
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.
341
experiences

5.0
Super!
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

5.0
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
September
€650
Per person

4.5
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
August
Starting from
€850
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
4 departures available
August - October
€650
Per person

4.9
Italy: Liguria
2 days - 2 nights
One departure available
August
€300
Per person

5.0
Super!
France: Corsica
7 days - 7 nights
One departure available
August
€1,050
Per person

5.0
Italy: Southern Sardinia
6 days - 7 nights
6 departures available
August - September
Starting from
€790
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€990
Per person

4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
September
€716
Per person

4.7
Italy: Tuscany
7 days - 6 nights
4 departures available
August - September
Starting from
€700
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
2 departures available
September
€790
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October - November
€250
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
18373 reviews
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
08/6/2026
Antonio C.
-
IT
Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera
08/6/2026
Franka G.
-
CH
Weekend on the island of Elba: among dolphins, enchanting bays and relaxation
08/6/2026
Daniela L.
-
IT
Discover the Egadi Paradise by sailboat from San Vito Lo Capo
08/6/2026
Nadia C.
-
IT
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