
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.
288
experiences

4.7
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
€795
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
8 departures available
August - October
Starting from
€1,300
€1,040
Per person

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August - October
Starting from
€700
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August
€1,100
Per person

5.0
Super!
Italy: Liguria
2 days - 1 night
One departure available
October
€220
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
August - September
€950
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€570
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
8 departures available
August - October
Starting from
€570
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - October
€690
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
Starting from
€585
€527
Per person

4.8
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
August - September
Starting from
€360
€300
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
18512 reviews
Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago
08/16/2026
Ilaria G.
-
IT
Vento di Sicilia: from the Aeolian Islands to Trapani
08/16/2026
Federica S.
-
IT
Enjoy the Aeolian Islands with skipper and hostess
08/16/2026
Elio V.
-
IT
Sailing cruise to the Pontine: wonders a stone's throw from Rome
08/16/2026
Alberto F.
-
IT
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