
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.
193
experiences

4.9
Greece: Cyclades
7 days - 7 nights
2 departures available
October
Starting from
€950
Per person

4.8
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

4.9
Italy: Aeolian Islands
3 days - 2 nights
7 departures available
September - October
€320
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
Starting from
€300
€270
Per person

5.0
Italy: Aegadian islands
7 days - 7 nights
One departure available
September
€620
Per person

4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€3,900
Per person

4.8
Italy: Aegadian islands
6 days - 7 nights
3 departures available
September - October
Starting from
€600
Per person

4.8
Italy: Southern Sardinia
6 days - 7 nights
One departure available
September
€790
Per person

5.0
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September
€890
Per person

4.1
Italy: Aeolian Islands
6 days - 7 nights
4 departures available
September - October
Starting from
€680
Per person

4.8
Italy: Tuscany
3 days - 3 nights
One departure available
September
€380
€361
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
6 departures available
September - October
Starting from
€585
€527
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
18971 reviews
A sailing holiday: discovering the Pontine Islands
08/31/2026
Matilde C.
-
IT
Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK
08/31/2026
Antonio C.
-
IT
Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica
08/31/2026
Giovanna B.
-
IT
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
08/31/2026
Luigi M.
-
IT
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