
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.
407
experiences

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

5.0
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
August
€949
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
7 departures available
August - November
Starting from
€500
€348
Per person

4.5
Spain: The Balearic Islands
6 days - 6 nights
3 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

4.8
Super!
Italy: Southern Sardinia
6 days - 7 nights
6 departures available
July - September
Starting from
€900
€855
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

4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
5 departures available
August - September
Starting from
€716
Per person

5.0
Super!
France: Corsica
3 days - 3 nights
One departure available
August
€290
Per person

4.4
France: Corsica
6 days - 7 nights
One departure available
August
€749
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
18165 reviews
A week in the Aeolian Islands - 6 islands in seven days
07/23/2026
Deborah T.
-
IT
Week end in Costa Azzurra
07/23/2026
Isabella R.
-
IT
The most spectacular islands of the Cyclades: from Athens to Milos
07/23/2026
Frank W.
-
DE
Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea
07/22/2026
chiara a.
-
IT
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