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
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
+17 travellers
have booked
Starting from
€225
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Tuscany
cosetta
has booked
€265
Per person
4.9
Duration:
2 days - 2 nights
Italy:
Liguria
+2 travellers
have booked
€275
Per person
4.2
Duration:
2 days - 2 nights
Italy:
Liguria
+5 travellers
have booked
Starting from
€250
Per person
4.4
Duration:
2 days - 1 night
Italy:
Liguria
+6 travellers
have booked
€200
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€1,350
Per person
Duration:
2 days - 1 night
Italy:
Liguria
Give this experience a try!
€199
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
€200
Per person
5.0
Duration:
2 days - 1 night
France:
Brittany and Normandy
Give this experience a try!
€250
Per person
4.9
Duration:
2 days - 2 nights
Croatia:
Istrian peninsula
Alberto B.
has booked
€249
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
+18 travellers
have booked
Starting from
€289
€340
Per person
5.0
Duration:
2 days - 1 night
France:
French Riviera and Porquerolles
+6 travellers
have booked
Starting from
€287
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
14273 reviews
May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms
05/2/2024
susanna s.
-
Italy
25 April - Whale watching expedition with WWF researcher in Liguria
05/2/2024
Rossella D.
-
Italy
LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba
05/1/2024
Simone D.
-
Switzerland
Long weekend in Capraia and North Corsica
04/30/2024
Licio M.
-
Italy
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