
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.
121
experiences

4.1
Italy: Aeolian Islands
6 days - 7 nights
One departure available
September - October
€680
Per person

5.0
New
France: French Riviera and Porquerolles
5 days - 4 nights
27 departures available
February - October
Starting from
€595
Per person

4.5
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€290
Per person

5.0
Italy: Liguria
2 days - 1 night
2 departures available
October
€320
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
October
€600
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
June
€625
Per person

5.0
New
Italy: Northern Sardinia
7 days - 7 nights
One departure available
September
€620
€590
Per person

Greece: Ionian Islands
7 days - 7 nights
2 departures available
October
€890
Per person

4.8
Italy: Lake Garda
1 day - 0 nights
8 departures available
September - October
€150
Per person

New
Premium
Greece: Ionian Islands
7 days - 7 nights
One departure available
September - October
Starting from
€1,645
Per person

5.0
Italy: Tuscany
4 days - 3 nights
One departure available
October
€400
Per person

5.0
New
Italy: Tuscany
2 days - 2 nights
3 departures available
October - November
€250
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
19208 reviews
Weekends immersed in the blue of the sea and the green of the island of Elba
09/25/2026
Raffaele A.
-
IT
Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings
09/25/2026
Sina Melina B.
-
DE
Long Weekend Santa Candida - Ventotene
09/25/2026
Claudio Giuseppe L.
-
IT
Sailing course in the Cyclades
09/24/2026
ruggero r.
-
IT
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