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.
528
experiences
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€410
Per person
5.0
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
August
€849
Per person
5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
July - September
Starting from
€690
€621
Per person
5.0
Croatia: Split Archipelago
7 days - 7 nights
10 departures available
June - October
Starting from
€1,200
Per person
5.0
Super!
Italy: Southern Sardinia
4 days - 3 nights
2 departures available
July - September
€740
Per person
4.8
Super!
Italy: Tuscany
7 days - 7 nights
5 departures available
August - October
€650
Per person
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€441
Per person
4.8
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
July
€590
Per person
4.9
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
July - September
€400
Per person
5.0
Italy: Aegadian islands
7 days - 7 nights
8 departures available
July - September
Starting from
€700
Per person
5.0
Italy: Aegadian islands
7 days - 7 nights
10 departures available
July - September
Starting from
€550
€495
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
17883 reviews
Pack your suitcase and we'll take care of the rest!! Stewards on board!
06/27/2026
Viviana M.
-
IT
Trip with photographer to the Pontine - Life changing experiences
06/27/2026
elena b.
-
IT
Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK
06/27/2026
Michele O.
A romantic and luxurious vacation in the Aeolian Islands
06/27/2026
Anna 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!
Follow us on
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
