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.
633
experiences
633
experiences
5.0
Duration:
6 days - 6 nights
Greece:
Ionian Islands
+17 travellers
have booked
Starting from
€550
Per person
4.9
Duration:
6 days - 6 nights
Greece:
Ionian Islands
+34 travellers
have booked
Starting from
€550
Per person
4.6
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+4 travellers
have booked
Starting from
€499
Per person
5.0
Duration:
6 days - 7 nights
Greece:
Ionian Islands
Give this experience a try!
€500
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!
€125
Per person
4.9
Duration:
6 days - 7 nights
Greece:
Saronic Islands and Athens area
+7 travellers
have booked
Starting from
€618
€650
Per person
5.0
Duration:
6 days - 7 nights
Greece:
Cyclades
+91 travellers
have booked
Starting from
€920
Per person
5.0
Duration:
5 days - 6 nights
Spain:
The Balearic Islands
+27 travellers
have booked
Starting from
€570
€600
Per person
4.8
Duration:
6 days - 7 nights
Greece:
Ionian Islands
Give this experience a try!
€570
Per person
Duration:
6 days - 6 nights
Italy:
Aeolian Islands
+4 travellers
have booked
Starting from
€650
Per person
5.0
Duration:
5 days - 4 nights
France:
French Riviera and Porquerolles
Give this experience a try!
Starting from
€630
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
14285 reviews
Weekend with wine tasting between Santa Margherita Ligure and Portofino
05/7/2024
Valentina B.
-
Italy
Week End Basic and Advanced Sailing Course
05/7/2024
Antonio R.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2024
enrico g.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2024
Irene T.
-
Italy
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