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.
503
experiences
503
experiences
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€935
€748
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
July - September
Starting from
€293
€264
Per person
4.8
Super!
Italy: Pantelleria and Lampedusa
6 days - 7 nights
9 departures available
August - October
Starting from
€850
€808
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
7 departures available
July - October
Starting from
€550
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
8 days - 7 nights
4 departures available
July - September
Starting from
€660
Per person
4.9
Super!
Italy: Liguria
2 days - 2 nights
One departure available
August
€350
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
10 departures available
July - October
Starting from
€550
Per person
4.7
Italy: Tuscany
6 days - 6 nights
4 departures available
July - September
Starting from
€1,041
€989
Per person
4.8
Super!
Italy: Pontine Islands
8 days - 7 nights
3 departures available
July - September
Starting from
€680
€544
Per person
4.9
Super!
Italy: Pontine Islands
3 days - 2 nights
6 departures available
July - September
Starting from
€370
€352
Per person
5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
9 departures available
July - September
Starting from
€790
€751
Per person
4.8
Italy: Aeolian Islands
6 days - 7 nights
11 departures available
July - October
Starting from
€530
€504
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
16134 reviews
Relaxing holiday on the Côte d'Azur
07/6/2025
VALENTINA D.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/6/2025
Dario B.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/6/2025
francesco f.
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/6/2025
Claudio S.
-
Italy
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