
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.
612
experiences

4.6
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€490
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
11 departures available
June - October
Starting from
€690
Per person

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

4.9
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
August
€890
Per person

4.6
Greece: Ionian Islands
7 days - 7 nights
2 departures available
August
Starting from
€874
€699
Per person

4.7
Italy: Tuscany
6 days - 6 nights
3 departures available
August - September
Starting from
€1,041
Per person
4.6
Italy: Tuscany
2 days - 2 nights
36 departures available
January - December
Starting from
€300
€270
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
6 departures available
June - September
Starting from
€650
€585
Per person

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

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

5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
11 departures available
June - September
Starting from
€790
Per person

5.0
Italy: Pontine Islands
3 days - 2 nights
2 departures available
July
€350
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
17762 reviews
June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide
06/10/2026
Guido F.
-
IT
Weekend in Ischia and Ventotene: History and Nature
06/10/2026
Michele F.
-
IT
June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene
06/10/2026
Donatella L.
-
IT
In the blue of Capri and the infinity of the Amalfi Coast
06/10/2026
Antonio D.
-
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