
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.
388
experiences

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

4.8
Super!
Italy: Tuscany
7 days - 6 nights
One departure available
August
€890
Per person

4.7
Croatia: Kornati Islands
6 days - 7 nights
3 departures available
August
Starting from
€800
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€920
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
Per person

New
Italy: Pantelleria and Lampedusa
7 days - 7 nights
6 departures available
August - November
Starting from
€500
€348
Per person

4.5
Spain: The Balearic Islands
6 days - 6 nights
2 departures available
August - September
Starting from
€1,010
Per person

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

5.0
Italy: Aeolian Islands
3 days - 2 nights
2 departures available
August
Starting from
€390
Per person
5.0
Italy: Tuscany
6 days - 6 nights
3 departures available
July - August
Starting from
€950
Per person

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

4.8
Super!
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August
€990
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
18197 reviews
Sailing from Tuscany to South Corsica
07/26/2026
Serena P.
-
IT
Aeolian Islands: sun, sport, music, good food... The rest is magic!
07/26/2026
Benedetto R.
-
IT
Sailing adventure in the sea of Ulysses - Stewardess on board
07/26/2026
Francesco Saverio C.
-
IT
Aeolian Islands: sun, sport, music, good food... The rest is magic!
07/26/2026
Camilla V.
-
IT
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