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.
126
experiences
126
experiences
4.8
Super!
Caribbean: Guadeloupe
7 days - 7 nights
9 departures available
January - December
€850
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
25 departures available
May - October
Starting from
€600
Per person
4.8
Super!
Caribbean: Guadeloupe
6 days - 6 nights
4 departures available
February - December
€730
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
18 departures available
May - October
Starting from
€689
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
2 departures available
October
€337
Per person
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
11 departures available
July - October
Starting from
€1,100
€1,045
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
26 departures available
March - September
Starting from
€650
€618
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
3 departures available
May - June
Starting from
€750
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€625
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
33 departures available
March - November
Starting from
€460
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
October - November
€583
Per person
4.8
Super!
Caribbean: Guadeloupe
5 days - 5 nights
One departure available
December
€650
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
17592 reviews
IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper
10/15/2025
Cinzia R.
-
Italy
Fantastic BARCOLANA: Racing in safety and joy!
10/15/2025
Giulia B.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
10/15/2025
Elena L.
-
Germany
Barcolana weekend in Trieste and surroundings.
10/15/2025
Barbara M.
-
Italy
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 2035144220Read our
Contact & SupportLet's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
