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.
466
experiences
466
experiences
5.0
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - November
Starting from
€650
€585
Per person
5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
8 departures available
July - September
Starting from
€790
€751
Per person
4.8
Italy: Northern Sardinia
6 days - 7 nights
11 departures available
July - October
Starting from
€615
Per person
4.8
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€640
Per person
4.7
Italy: Tuscany
6 days - 7 nights
7 departures available
July - September
Starting from
€1,041
€989
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
7 days - 7 nights
2 departures available
August
€950
Per person
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
13 departures available
July - October
Starting from
€400
€360
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
7 departures available
July - September
Starting from
€550
Per person
4.8
Italy: Tuscany
3 days - 2 nights
5 departures available
July - October
Starting from
€240
€228
Per person
4.8
Super!
Italy: Pontine Islands
8 days - 7 nights
2 departures available
August - September
Starting from
€660
Per person
4.9
Super!
Italy: Tuscany
7 days - 7 nights
2 departures available
July - August
Starting from
€870
Per person
4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€1,080
€918
Per person - min 2 pax
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
16246 reviews
We have known the Aeolian Islands for 20 years, live them with us!
07/15/2025
Arianna O.
Life-changing experiences - Escape to the Pontine Islands
07/15/2025
Anna R.
-
Italy
Weekend on Elba Island
07/15/2025
Dalgisa B.
-
Italy
Long weekend among the queens of the archipelago - Elba and Capraia
07/15/2025
Laurence B.
-
Belgium
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