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.
461
experiences
461
experiences
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€935
€748
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
11 departures available
July - October
Starting from
€615
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€820
Per person
4.9
Super!
Italy: Tuscany
6 days - 5 nights
5 departures available
July - August
Starting from
€650
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
10 departures available
July - October
Starting from
€550
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
6 departures available
August - October
Starting from
€550
Per person
4.8
Italy: Aeolian Islands
6 days - 7 nights
10 departures available
July - October
Starting from
€530
€504
Per person
4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€300
Per person
4.8
Super!
Italy: Pantelleria and Lampedusa
6 days - 7 nights
9 departures available
August - October
Starting from
€850
€808
Per person
4.9
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€850
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
August - September
Starting from
€689
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
September
€293
€264
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
16268 reviews
Pontine Islands aboard a splendid 16-meter sailboat
07/18/2025
Sabrina C.
-
Italy
Pontine Islands aboard a splendid 16-meter sailboat
07/18/2025
Laura D.
-
Italy
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
07/18/2025
Nathalie B.
-
France
Pontine Islands aboard a splendid 16-meter sailboat
07/18/2025
Jennifer D.
-
Italy
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