
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.
368
experiences

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€200
Per person

4.7
Italy: Tuscany
7 days - 6 nights
5 departures available
August - September
Starting from
€700
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
4 departures available
August - September
Starting from
€1,450
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€920
Per person

4.7
Italy: Pontine Islands
3 days - 2 nights
4 departures available
August - September
Starting from
€312
Per person

4.8
Italy: Naples & Amalfi Coast
4 days - 3 nights
One departure available
September
€333
Per person

5.0
Super!
Spain: The Balearic Islands
6 days - 6 nights
One departure available
September
€750
€675
Per person

4.7
Italy: Liguria
4 days - 4 nights
One departure available
September
€609
€579
Per person

4.5
Spain: The Balearic Islands
6 days - 6 nights
2 departures available
August - September
Starting from
€1,010
Per person

5.0
Super!
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

5.0
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
September
€650
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
4 departures available
August - October
€650
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
18272 reviews
Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera
08/1/2026
Fabrizio S.
-
IT
Capri Light Blue - Two boats in company!
08/1/2026
Maria bruna M.
-
IT
Two days at the Marine Protected Area of the Tremiti Islands
08/1/2026
Elisabetta M.
-
IT
North Sardinia and Corsica: blue seen from a sailboat
08/1/2026
Gabriele T.
-
IT
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