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.
123
experiences
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
23 departures available
May - October
Starting from
€1,200
€1,080
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
17 departures available
June - October
Starting from
€660
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
October - November
€585
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
33 departures available
March - October
Starting from
€460
Per person
4.9
Super!
France: French Riviera and Porquerolles
6 days - 7 nights
8 departures available
July - August
Starting from
€800
Per person
4.9
Super!
France: Corsica
7 days - 6 nights
4 departures available
August
Starting from
€750
Per person
4.8
Super!
Italy: Tuscany
6 days - 6 nights
13 departures available
June - September
Starting from
€990
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
10 departures available
May - July
Starting from
€650
€585
Per person
5.0
Super!
Italy: Sicily
1 day - 0 nights
15 departures available
October - November
€150
Per person
5.0
Super!
Pacific Ocean: French Polynesia
13 days - 13 nights
One departure available
October - November
€2,090
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October - November
€300
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€280
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
19283 reviews
IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper
10/19/2026
Chloe Maira G.
-
IT
The fantastic Saronic Islands and the surroundings of Athens
10/19/2026
ASLIHAN A.
-
TR
Magical Barcolana Weekend: the most famous regatta!
10/19/2026
LUIGI L.
-
IT
Barcolana 58: a day at the most famous regatta in the world
10/18/2026
Laura P.
-
IT
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