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.
497
experiences
497
experiences
Duration:
6 days - 6 nights
Spain:
The Balearic Islands
+7 travellers
have booked
Starting from
€700
€1,400
Per person
4.8
Super!
Duration:
7 days - 7 nights
Italy:
Tuscany
+40 travellers
have booked
Starting from
€450
€880
Per person
4.5
Duration:
6 days - 7 nights
Croatia:
Istrian peninsula
+7 travellers
have booked
€500
€850
Per person
5.0
Super!
Duration:
6 days - 6 nights
Italy:
Tuscany
+30 travellers
have booked
Starting from
€390
€650
Per person
4.6
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+152 travellers
have booked
Starting from
€799
€1,175
Per person
5.0
Duration:
9 days - 10 nights
Italy:
Aegadian islands
+10 travellers
have booked
€1,100
€1,500
Per person
4.8
Duration:
7 days - 6 nights
Italy:
Tuscany
+3 travellers
have booked
€799
€1,099
Per person
5.0
Duration:
7 days - 7 nights
Italy:
Naples & Amalfi Coast
+24 travellers
have booked
Starting from
€1,100
€1,490
Per person
Duration:
8 days - 7 nights
Greece:
Cyclades
Give this experience a try!
€593
€790
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Tuscany
+6 travellers
have booked
Starting from
€650
€830
Per person
3.1
Duration:
10 days - 10 nights
Greece:
Sporades
+15 travellers
have booked
Starting from
€1,312
€1,640
Per person
4.9
Super!
Duration:
4 days - 3 nights
Italy:
Tuscany
+2 travellers
have booked
€479
€599
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
14736 reviews
Week between the Tuscan Islands and North Corsica
07/26/2024
Gianmarco N.
-
Italy
Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor
07/26/2024
Katia P.
-
Italy
4 days in the Pontine Islands (sailing school)
07/26/2024
valentina P.
-
Luxembourg
From Cinque Terre to Tigullio, discovering Ligurian pearls
07/26/2024
Chiara C.
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