
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.
483
experiences

5.0
Italy: Aegadian islands
7 days - 7 nights
8 departures available
July - September
Starting from
€550
€495
Per person

4.8
Super!
Italy: Pontine Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€900
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
July - September
Starting from
€200
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
7 departures available
July - September
Starting from
€1,450
Per person
4.9
Super!
Italy: Pontine Islands
6 days - 6 nights
2 departures available
August - September
€1,100
Per person

5.0
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
August
€949
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
3 departures available
August - September
Starting from
€950
Per person

4.7
Italy: Pontine Islands
4 days - 3 nights
2 departures available
July - August
Starting from
€437
Per person

4.7
Italy: Liguria
6 days - 6 nights
2 departures available
July - August
Starting from
€946
Per person

4.7
New
Italy: Aegadian islands
7 days - 7 nights
5 departures available
July - September
Starting from
€600
€540
Per person

4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
September
€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
18026 reviews
Midweek relaxing in the Pontine Islands
07/12/2026
Riccardo G.
-
IT
Sailing cruise to the Pontine: wonders a stone's throw from Rome
07/12/2026
valentina t.
-
IT
Mini whale watching cruise with WWF guide between Ponza and Palmarola
07/11/2026
beatrice c.
-
IT
4 Days Argentario-Giannutri-Giglio-Talamone
07/11/2026
Francesca M.
-
IT
Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 20 3514 4220Read our
Contact & SupportLet's talk Sailsquare!



Secure payments



© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964