
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.
107
experiences
4.1
Italy: Tuscany
2 days - 2 nights
35 departures available
January - December
Starting from
€275
€248
Per person

4.8
Italy: Naples & Amalfi Coast
1 day - 0 nights
90 departures available
July - September
€150
Per person

New
Italy: Pontine Islands
3 days - 2 nights
2 departures available
May
€400
Per person

4.8
Atlantic islands: Canary Islands
6 days - 7 nights
One departure available
December
€900
Per person

4.3
Malta: Malta
6 days - 6 nights
12 departures available
July - September
Starting from
€745
Per person

4.7
Italy: Liguria
2 days - 2 nights
One departure available
April - May
€300
Per person

Spain: The Balearic Islands
7 days - 7 nights
One departure available
April
€1,950
€1,755
Per person

4.8
Italy: Southern Sardinia
7 days - 7 nights
5 departures available
August - September
Starting from
€830
Per person
5.0
Italy: Tuscany
6 days - 6 nights
6 departures available
July - August
Starting from
€801
Per person

New
Italy: Pontine Islands
3 days - 2 nights
5 departures available
June - July
€400
€360
Per person

4.5
Italy: Northern Sardinia
6 days - 7 nights
9 departures available
July - September
Starting from
€688
Per person

5.0
Italy: Naples & Amalfi Coast
1 day - 0 nights
19 departures available
November - December
€100
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
19290 reviews
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
11/3/2026
Alvise V.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
The fantastic Saronic Islands and the surroundings of Athens
10/20/2026
Francesca A.
-
IT
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