
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.
125
experiences

4.8
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€200
Per person

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

4.5
New
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
September - October
€890
Per person

5.0
Italy: Liguria
2 days - 2 nights
4 departures available
October - November
Starting from
€380
Per person

4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€4,200
Per person

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
4 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
€890
Per person

5.0
Croatia: Split Archipelago
7 days - 7 nights
3 departures available
September - October
€1,100
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
19162 reviews
North Corsica & Tuscan Archipelago: we love to travel a lot
09/19/2026
francesca vera p.
-
IT
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
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