
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.
504
experiences

4.5
Italy: Aeolian Islands
7 days - 7 nights
12 departures available
August - November
Starting from
€540
€513
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
6 departures available
July - October
Starting from
€650
€585
Per person

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
6 departures available
July - October
Starting from
€420
€399
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
7 departures available
July - October
Starting from
€230
Per person

4.8
Super!
Italy: Tuscany
3 days - 3 nights
2 departures available
July - August
Starting from
€440
€396
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
July - August
€900
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
6 days - 6 nights
2 departures available
July - August
Starting from
€1,150
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
4 departures available
July - September
Starting from
€490
€466
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€900
€750
Per person

4.8
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
July
€590
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
8 departures available
July - October
Starting from
€750
€675
Per person

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
One departure available
September
€620
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
17999 reviews
Four days in the Pontine Islands, just a stone's throw from Rome
07/8/2026
Francesco O.
-
IT
Corfu between bays, taverns and myths.
07/8/2026
Farida B.
-
IT
Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company
07/8/2026
Fabio C.
-
IT
Long weekend between Ponza and Palmarola: adventure at the Pontine!
07/8/2026
ELISABETTA P.
-
IT
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