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.
630
experiences
630
experiences
4.8
Duration:
2 days - 2 nights
Italy:
Amalfi Coast
Give this experience a try!
€298
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Aeolian Islands
Give this experience a try!
€265
Per person
4.8
Duration:
3 days - 2 nights
Italy:
Amalfi Coast
+18 travellers
have booked
€450
Per person
4.6
Duration:
2 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€200
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Pontine Islands
+30 travellers
have booked
Starting from
€248
€275
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Amalfi Coast
+12 travellers
have booked
Starting from
€261
€275
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+7 travellers
have booked
€200
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€300
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+18 travellers
have booked
Starting from
€261
€275
Per person
5.0
Duration:
6 days - 7 nights
Greece:
Cyclades
+4 travellers
have booked
€500
Per person
Duration:
7 days - 6 nights
Greece:
Dodecanese
Give this experience a try!
€1,653
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+2 travellers
have booked
Starting from
€290
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
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