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.
627
experiences
627
experiences
4.9
Duration:
6 days - 6 nights
Greece:
Ionian Islands
+32 travellers
have booked
Starting from
€510
Per person
5.0
Duration:
6 days - 6 nights
Greece:
Ionian Islands
+15 travellers
have booked
Starting from
€510
Per person
5.0
Duration:
6 days - 7 nights
Greece:
Ionian Islands
Give this experience a try!
€550
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Lake Maggiore
Give this experience a try!
€130
Per person
4.9
Duration:
6 days - 5 nights
France:
Channel Islands
+18 travellers
have booked
Starting from
€745
Per person
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€120
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
+12 travellers
have booked
Starting from
€126
€140
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+25 travellers
have booked
€99
Per person
4.4
Duration:
1 day - 0 nights
Italy:
Northern Sardinia
Give this experience a try!
€90
Per person
Duration:
7 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
€299
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+4 travellers
have booked
Starting from
€1,100
Per person
4.8
Duration:
3 days - 3 nights
Italy:
Tuscany
+7 travellers
have booked
€300
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
14264 reviews
A weekend of sailing between Capraia and the island of Elba
04/24/2024
Angelo C.
-
Italy
Easter on the Island of Elba
04/22/2024
Antonios S.
-
Italy
Trekking and sailing weekend on the island of Elba
04/22/2024
Sara C.
-
Italy
Luxury sailing in the Gulf of Poets
04/15/2024
Antonio C.
-
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!
Sailsquare
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964