
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.
124
experiences

5.0
Italy: Aeolian Islands
7 days - 7 nights
One departure available
September - October
€690
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€730
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
3 departures available
September - October
Starting from
€585
Per person

4.6
Italy: Sicily
4 days - 3 nights
One departure available
September
€345
Per person

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

4.4
Atlantic islands: Canary Islands
10 days - 10 nights
One departure available
November
€1,100
€990
Per person

4.0
Spain: Andalusia
9 days - 9 nights
One departure available
October - November
€550
Per person
4.1
Italy: Tuscany
2 days - 2 nights
26 departures available
January - December
Starting from
€300
€270
Per person

4.7
Spain: The Balearic Islands
6 days - 7 nights
One departure available
October
€900
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
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
19192 reviews
Weekend in the Pontine Islands
09/22/2026
Alice P.
-
IT
Gulf of Poets
09/22/2026
Paolo D.
Amazing Pontine Islands on a sailboat with private bathrooms
09/22/2026
Roberta P.
-
IT
Sporades Experience: Freedom, Turquoise Sea and Greek Magic
09/22/2026
Aida K.
-
BA
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