
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.
195
experiences

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
6 departures available
September - October
Starting from
€1,300
€1,040
Per person

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

4.7
Italy: Pontine Islands
3 days - 3 nights
One departure available
September
€420
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
September - October
Starting from
€700
Per person

5.0
Super!
Italy: Pontine Islands
5 days - 4 nights
One departure available
September
€550
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
September
€490
€441
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
October
€570
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
Starting from
€585
€527
Per person

4.7
Italy: Tuscany
3 days - 3 nights
3 departures available
September
Starting from
€441
€419
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
September - October
Starting from
€750
€675
Per person

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

5.0
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
€690
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
19012 reviews
Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean
09/3/2026
Martina P.
-
IT
Egadi Sail & Relax: the archipelago to experience
09/3/2026
Leandro D.
-
IT
7 days of sailing between beautiful Croatian islands and crystal clear waters
09/3/2026
Domenico F.
-
IT
Between the Pontine Islands and the Phlegraean Islands by Sailing Boat
09/3/2026
Walter G.
-
IT
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