
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.
196
experiences

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
6 departures available
September - October
Starting from
€370
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
October
€453
€430
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
3 departures available
September
€490
€466
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
3 departures available
September - October
€650
Per person

4.9
Super!
North Sea: Norway
11 days - 11 nights
One departure available
December - January
€1,300
Per person
5.0
Super!
Greece: Cyclades
6 days - 6 nights
2 departures available
September
Starting from
€1,000
€750
Per person

4.9
Super!
North Sea: Norway
7 days - 7 nights
One departure available
October
€1,200
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September - October
€835
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€980
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€250
€225
Per person

5.0
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€350
Per person

4.7
Spain: The Balearic Islands
6 days - 7 nights
2 departures available
September
€1,290
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
19005 reviews
Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY
09/3/2026
Francesca L.
-
IT
Gulf of Poets
09/2/2026
Caterina G.
-
IT
The perfect holiday on Europe's hottest and most glamorous island
09/2/2026
Giorgia S.
-
IT
Marmaglia Discovery Flotilla to the Cyclades Islands in Greece
09/2/2026
Rafaela C.
-
IT
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