
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.
152
experiences

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

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

4.8
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
September - October
Starting from
€700
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

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

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
5 departures available
September - October
Starting from
€370
Per person

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

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

5.0
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
September
€620
Per person

4.8
Super!
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
October
€750
Per person

5.0
New
Italy: Liguria
2 days - 1 night
One departure available
October
€220
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
19121 reviews
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
09/13/2026
Elisa V.
-
IT
Whale watching cruise with WWF guide between Northern Sardinia and South Corsica
09/13/2026
Matteo F.
-
IT
Sailing holiday in the archipelago of La Maddalena and Costa Smeralda
09/13/2026
Polyanne M.
-
ES
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
09/13/2026
Carolina V.
-
US
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