
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.
411
experiences

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
€1,041
Per person

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

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

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
3 departures available
August - September
Starting from
€950
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
3 departures available
August - September
Starting from
€1,200
€990
Per person

4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
August
€800
Per person

4.4
France: French Riviera and Porquerolles
6 days - 7 nights
8 departures available
July - September
Starting from
€730
€657
Per person

5.0
Super!
Italy: Liguria
2 days - 2 nights
One departure available
July - August
€400
€360
Per person

4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€280
Per person

4.8
Super!
Italy: Tuscany
4 days - 3 nights
4 departures available
August - September
Starting from
€400
€360
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
3 departures available
August - September
Starting from
€583
Per person
4.1
Italy: Tuscany
2 days - 2 nights
31 departures available
January - December
€300
€270
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
18162 reviews
Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea
07/22/2026
chiara a.
-
IT
Sailing cruise to the Pontine: wonders a stone's throw from Rome
07/22/2026
Francesca C.
-
IT
Aeolian Islands: sun, sport, music, good food... The rest is magic!
07/22/2026
Giulio A.
-
GB
Ponza and Palmarola: three days of pure relaxation
07/22/2026
Marco Q.
-
IT
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