
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.
595
experiences

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

4.8
Super!
Italy: Tuscany
6 days - 7 nights
6 departures available
July - September
Starting from
€900
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!
Greece: Sporades
7 days - 7 nights
3 departures available
July - September
Starting from
€750
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
July - August
Starting from
€850
€765
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
June
€750
€675
Per person

5.0
Super!
Croatia: Split Archipelago
7 days - 7 nights
11 departures available
June - October
Starting from
€1,200
Per person

5.0
New
Italy: Aegadian islands
7 days - 7 nights
7 departures available
June - September
Starting from
€650
€585
Per person

4.7
Greece: Ionian Islands
6 days - 7 nights
One departure available
July - August
€1,052
Per person

4.9
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
July - September
€400
Per person

4.5
Italy: Aeolian Islands
7 days - 7 nights
17 departures available
July - November
Starting from
€540
€513
Per person

5.0
Greece: Ionian Islands
7 days - 7 nights
16 departures available
June - October
Starting from
€570
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
17773 reviews
Afternoon, aperitif and sunset on Verbano - Lake Maggiore
06/14/2026
Enrico C.
-
IT
A sensory sailing journey between volcanoes and a marine paradise
06/14/2026
Diana B.
-
IT
North Sardinia and Corsica: blue seen from a sailboat
06/14/2026
Matteo B.
Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!
06/14/2026
Maddalena G.
-
ES
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