
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.
633
experiences

4.7
Italy: Pantelleria and Lampedusa
6 days - 7 nights
8 departures available
August - October
Starting from
€860
€774
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
19 departures available
May - October
Starting from
€640
€576
Per person

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
8 departures available
May - October
Starting from
€320
€272
Per person

4.7
Italy: Tuscany
6 days - 6 nights
4 departures available
August - September
Starting from
€1,041
€989
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
14 departures available
May - October
Starting from
€230
Per person

4.9
Super!
Italy: Liguria
2 days - 2 nights
3 departures available
July - September
Starting from
€390
Per person

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
7 departures available
June - October
Starting from
€700
Per person

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
8 departures available
June - October
Starting from
€420
€399
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
13 departures available
May - September
Starting from
€400
€380
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
7 departures available
June - September
Starting from
€583
€525
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
12 departures available
May - October
Starting from
€230
Per person

4.7
Italy: Tuscany
6 days - 7 nights
5 departures available
July - August
Starting from
€1,094
€1,039
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
17636 reviews
4 Days Exploring the Chausey Islands from Saint-Malo
04/30/2026
Claire M.
-
France
Sailing cruise in the Greek islands - The Saronic Islands
04/29/2026
Marc G.
-
Canada
April 25th: cetacean watching expedition in the Pelagos Sanctuary with WWF guide
04/28/2026
Michele B.
-
Italy
April 25th long weekend on the Island of Elba
04/27/2026
Andrea T.
-
Italy
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