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.
244
experiences
244
experiences
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
September - October
Starting from
€550
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
8 departures available
September - October
Starting from
€337
Per person
4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
August - September
Starting from
€690
€529
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
September
€750
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
5 departures available
September - October
Starting from
€337
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
4 departures available
September - November
Starting from
€650
€618
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€750
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
September - October
€690
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
August - September
€689
Per person
4.6
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
September
Starting from
€750
Per person
5.0
Super!
Greece: Dodecanese
8 days - 8 nights
One departure available
September
€650
Per person
4.8
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
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
17178 reviews
Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms
08/30/2025
Samantha P.
-
Italy
Wild Sardinia, a cruise shared with nature
08/30/2025
Valeria I.
-
Italy
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
08/30/2025
Angela M.
-
Italy
La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine
08/30/2025
Roberta C.
-
Italy
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