
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.
409
experiences

4.5
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
Starting from
€1,260
€1,070
Per person

4.7
Croatia: Kornati Islands
7 days - 7 nights
2 departures available
August
Starting from
€1,180
€980
Per person

4.7
Greece: Cyclades
6 days - 7 nights
One departure available
August
€1,290
€1,190
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August
Starting from
€920
Per person

4.7
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€795
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
10 departures available
August - October
Starting from
€1,400
€1,120
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
9 departures available
August - October
Starting from
€590
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€600
€570
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
3 departures available
August - September
Starting from
€900
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€870
Per person

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

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
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
18163 reviews
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
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
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