
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.
547
experiences

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

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
July
€410
Per person

5.0
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
August
€849
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
September - November
€250
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
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: Southern Sardinia
4 days - 3 nights
2 departures available
July - September
€740
Per person

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

4.9
Super!
Croatia: Istrian peninsula
3 days - 2 nights
6 departures available
July - October
€260
Per person

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€441
Per person

4.8
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
July
€590
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
July - September
Starting from
€200
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
17870 reviews
From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen
06/24/2026
Cesare S.
-
IT
We have known the Aeolian Islands for 20 years, live them with us!
06/24/2026
Alessandro O.
-
IT
Mini-cruise with WWF guide in the heart of the Tuscan Archipelago
06/24/2026
Giovanni G.
-
IT
Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!
06/24/2026
Isla W.
-
CA
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