
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.
644
experiences

4.9
Super!
Italy: Aegadian islands
3 days - 2 nights
2 departures available
May
€350
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
4 departures available
May - July
Starting from
€350
Per person

New
Italy: Aegadian islands
7 days - 7 nights
12 departures available
May - September
Starting from
€600
€540
Per person

5.0
Super!
Italy: Pontine Islands
7 days - 7 nights
One departure available
August
€650
Per person

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

5.0
Greece: Ionian Islands
7 days - 7 nights
20 departures available
May - October
Starting from
€550
Per person

4.9
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
June - September
€280
Per person

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

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
5 departures available
June - July
Starting from
€285
Per person

4.9
Super!
Italy: Tuscany
3 days - 3 nights
3 departures available
July - August
Starting from
€410
€369
Per person

4.4
France: French Riviera and Porquerolles
6 days - 7 nights
13 departures available
June - September
Starting from
€730
€657
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
13 departures available
May - October
Starting from
€800
€720
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
17663 reviews
Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola
05/12/2026
Paola A.
-
Italy
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
05/11/2026
Lucia K.
-
Switzerland
May Day between Elba and Capraia
05/11/2026
Valeria C.
-
Italy
Relaxing weekend in the Pontine Islands
05/11/2026
Flavia F.
-
Italy
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