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.
499
experiences
499
experiences
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€935
€748
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
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
7 departures available
July - September
Starting from
€689
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
Italy: Aeolian Islands
6 days - 7 nights
11 departures available
July - October
Starting from
€530
€504
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: Tuscany
6 days - 5 nights
6 departures available
July - August
Starting from
€650
Per person
4.9
Super!
Italy: Pontine Islands
3 days - 2 nights
6 departures available
July - September
Starting from
€370
€352
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
16167 reviews
Weekend on Elba Island
07/8/2025
Giovanna B.
-
Italy
Three-Day Sailing Tour to the Pontine Islands
07/8/2025
Serena R.
-
Italy
Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess
07/8/2025
sonia s.
-
Italy
Ibiza All Inclusive on an 18m ketch with skipper and skipper
07/8/2025
Donatella R.
-
Italy
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