
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.
617
experiences

5.0
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August - September
€1,020
Per person

4.9
Super!
Italy: Tuscany
6 days - 6 nights
11 departures available
June - September
Starting from
€980
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
11 departures available
May - October
Starting from
€800
€720
Per person

5.0
Italy: Tuscany
3 days - 3 nights
2 departures available
July - September
Starting from
€350
Per person

4.9
Super!
Italy: Aegadian islands
3 days - 2 nights
One departure available
May
€350
Per person

4.6
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
€1,260
€1,134
Per person

4.7
Greece: Ionian Islands
6 days - 7 nights
One departure available
July - August
€1,052
€999
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
2 departures available
June - July
Starting from
€440
Per person

5.0
Super!
Italy: Aeolian Islands
3 days - 2 nights
10 departures available
June - August
Starting from
€390
€351
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
11 departures available
May - October
Starting from
€500
Per person

4.9
Super!
Croatia: Istrian peninsula
3 days - 2 nights
8 departures available
June - October
€260
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
June
€300
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
17678 reviews
In the blue of Capri and the infinity of the Amalfi Coast
05/26/2026
Ludovica L.
-
IT
Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company
05/26/2026
Claudia M.
-
IT
In the blue of Capri and the infinity of the Amalfi Coast
05/26/2026
Mariaelena P.
-
IT
A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia
05/26/2026
Michele P.
-
IT
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