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.
192
experiences
5.0
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October - November
€250
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
3 departures available
September - October
€750
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
7 departures available
September - October
Starting from
€230
Per person
5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
September
€950
Per person
4.9
Super!
Croatia: Istrian peninsula
3 days - 2 nights
One departure available
September
€260
Per person
4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
September
Starting from
€700
Per person
5.0
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
September
€620
Per person
5.0
Super!
Greece: Sporades
7 days - 7 nights
One departure available
September
€620
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September
€700
Per person
4.7
Italy: Pontine Islands
3 days - 2 nights
2 departures available
September
Starting from
€312
Per person
5.0
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
2 departures available
October
€950
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
September
€716
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
18976 reviews
Just relaxing while sailing on the Côte d'Azur
09/1/2026
Christine S.
-
FR
Gulf of Poets
09/1/2026
Maria P.
-
IT
Private afternoon tour on Lake Garda
09/1/2026
Federica B.
-
IT
Pack your suitcase and we'll take care of the rest!! Stewards on board!
09/1/2026
CRISTINA G.
-
IT
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