
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.
338
experiences

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
One departure available
August
€850
Per person

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

4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
4 departures available
September - October
Starting from
€600
€540
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€845
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
18376 reviews
The Island of Elba, to make you live a special experience!
08/7/2026
Carlotta T.
-
IT
Two days at the Marine Protected Area of the Tremiti Islands
08/7/2026
Gioia F.
-
BE
Sailing cruise to the Pontine: wonders a stone's throw from Rome
08/7/2026
Manuel C.
-
IT
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
08/6/2026
Antonio C.
-
IT
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