
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.
609
experiences

4.8
Italy: Naples & Amalfi Coast
7 days - 7 nights
One departure available
August
€977
€879
Per person

4.6
Italy: Tuscany
7 days - 6 nights
3 departures available
July - August
Starting from
€800
Per person

5.0
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August - September
€1,020
Per person

5.0
Super!
Italy: Tuscany
6 days - 6 nights
2 departures available
August
Starting from
€849
Per person

4.9
Super!
Italy: Tuscany
6 days - 6 nights
11 departures available
June - September
Starting from
€980
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
Per person

5.0
Super!
Italy: Tuscany
7 days - 7 nights
2 departures available
August
Starting from
€1,060
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
July - September
Starting from
€690
€621
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
One departure available
July
€495
€446
Per person

5.0
Super!
Italy: Aeolian Islands
3 days - 2 nights
10 departures available
June - August
Starting from
€390
€351
Per person

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

4.9
Super!
Croatia: Istrian peninsula
3 days - 2 nights
6 departures available
July - October
€260
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
17763 reviews
Summer is made for the Aeolian Islands! Weekly cruise
06/11/2026
Patrizia R.
-
IT
June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide
06/10/2026
Guido F.
-
IT
Weekend in Ischia and Ventotene: History and Nature
06/10/2026
Michele F.
-
IT
June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene
06/10/2026
Donatella L.
-
IT
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