
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.
282
experiences

4.8
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
September - October
Starting from
€230
Per person

4.9
Super!
Italy: Aeolian Islands
3 days - 3 nights
One departure available
September
€400
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€800
Per person - min 2 pax

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

5.0
Super!
Greece: Cyclades
6 days - 6 nights
One departure available
September - October
€950
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
5 days - 5 nights
One departure available
September
€1,150
Per person

5.0
Super!
Croatia: Kornati Islands
6 days - 6 nights
One departure available
August
€870
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
6 departures available
September - October
Starting from
€370
Per person

5.0
Super!
Pacific Ocean: French Polynesia
13 days - 13 nights
One departure available
October - November
€2,090
Per person

4.7
Italy: Pontine Islands
3 days - 2 nights
3 departures available
August - September
Starting from
€312
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
5 departures available
August - September
€600
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
7 departures available
September - October
Starting from
€370
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
18617 reviews
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
08/18/2026
Eva R.
-
IT
Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean
08/18/2026
federica s.
-
IT
North Corsica & Tuscan Archipelago: we love to travel a lot
08/18/2026
Eleonora M.
-
IT
Five days in Croatia with skipper, instructor and cook
08/18/2026
Alice P.
-
IT
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