
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.
134
experiences

4.7
Italy: Tuscany
2 days - 2 nights
One departure available
October
€180
Per person

4.0
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,290
Per person

4.4
Atlantic islands: Canary Islands
10 days - 10 nights
One departure available
November
€890
Per person

4.7
Greece: Ionian Islands
6 days - 7 nights
One departure available
September
€600
Per person

5.0
Croatia: Split Archipelago
7 days - 7 nights
3 departures available
September - October
€1,100
Per person

4.7
Spain: The Balearic Islands
6 days - 7 nights
One departure available
October
€900
Per person

4.0
Greece: Peloponnese
6 days - 6 nights
One departure available
September
€815
Per person

4.0
Atlantic islands: Canary Islands
6 days - 6 nights
One departure available
November
€660
Per person

5.0
Italy: Sicily
2 days - 1 night
5 departures available
September - October
Starting from
€215
€194
Per person

4.0
France: French Riviera and Porquerolles
6 days - 6 nights
One departure available
October
€550
Per person

5.0
Spain: The Balearic Islands
6 days - 6 nights
4 departures available
September - October
Starting from
€950
Per person

5.0
New
France: French Riviera and Porquerolles
5 days - 4 nights
27 departures available
February - October
Starting from
€595
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
19161 reviews
Five days barefoot between Tuscany and Corsica
09/19/2026
Mariella D.
-
IT
A sailing story between Favignana, Levanzo and Marettimo
09/19/2026
Alessandro P.
-
IT
Five days barefoot between Tuscany and Corsica
09/18/2026
daniela s.
-
IT
A week sailing in the most beautiful places in the world
09/18/2026
Davide G.
-
IT
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