
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.
100
experiences

4.9
Italy: Aeolian Islands
3 days - 2 nights
3 departures available
October
€320
Per person

5.0
Croatia: Split Archipelago
7 days - 7 nights
One departure available
October
€1,100
Per person

5.0
Indian Ocean: Indonesia
12 days - 12 nights
One departure available
December - January
€2,070
Per person

4.8
Italy: Tuscany
3 days - 2 nights
One departure available
October
€332
€299
Per person

4.4
Caribbean: Saint Martin
14 days - 14 nights
One departure available
February
€1,490
€1,341
Per person

5.0
Italy: Aeolian Islands
2 days - 2 nights
4 departures available
October - November
€723
Per person

4.7
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
October - November
€700
€665
Per person

4.7
Atlantic islands: Canary Islands
6 days - 7 nights
10 departures available
January - December
Starting from
€900
Per person

5.0
New
Italy: Liguria
2 days - 1 night
3 departures available
October - November
Starting from
€220
€198
Per person

New
Italy: Pontine Islands
3 days - 2 nights
2 departures available
May
€450
Per person

4.7
Atlantic islands: Canary Islands
6 days - 7 nights
One departure available
December
Starting from
€900
Per person

4.3
Malta: Malta
6 days - 6 nights
2 departures available
October
€690
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
19249 reviews
Sailing, swimming and aperitif at sunset ... What else?
10/3/2026
Victoire D.
-
FR
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
10/3/2026
Marina G.
-
IL
Sailing, sun and sea in the Tuscan Archipelago
10/3/2026
Luca P.
-
IT
Split archipelago, Hvar islands, Brac - with Hostess and full board
10/3/2026
Jean michel S.
-
BE
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