
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.
612
experiences

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
19 departures available
April - October
Starting from
€460
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
17 departures available
May - October
Starting from
€689
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
16 departures available
May - October
Starting from
€650
€585
Per person

4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
27 departures available
April - November
Starting from
€650
€618
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
9 departures available
May - July
Starting from
€650
€585
Per person

4.8
Super!
Greece: Cyclades
7 days - 7 nights
2 departures available
August
€990
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
12 departures available
May - September
Starting from
€1,300
€1,170
Per person

5.0
Super!
Greece: Sporades
7 days - 7 nights
5 departures available
July - September
Starting from
€650
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
20 departures available
May - October
Starting from
€590
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
22 departures available
May - November
Starting from
€600
€540
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
21 departures available
May - October
Starting from
€640
€576
Per person

4.6
Italy: Pontine Islands
3 days - 2 nights
7 departures available
May - June
Starting from
€230
€207
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
17626 reviews
Easter on the Island of Elba
04/9/2026
Miriam C.
-
Italy
Easter in Capraia and Corsica
04/9/2026
Monica L.
-
Italy
Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide
04/8/2026
Agnese F.
-
Italy
Easter in Capraia and Corsica
04/8/2026
Giovanni G.
-
Italy
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