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.
493
experiences
493
experiences
4.9
Super!
Italy: Tuscany
3 days - 3 nights
2 departures available
July - August
€395
€375
Per person
4.8
Italy: Pontine Islands
4 days - 3 nights
3 departures available
July - September
Starting from
€270
Per person
4.8
Italy: Northern Sardinia
6 days - 7 nights
12 departures available
July - October
Starting from
€615
Per person
4.8
Super!
Italy: Pantelleria and Lampedusa
7 days - 7 nights
One departure available
July - August
€679
€543
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
6 departures available
July - November
Starting from
€650
€618
Per person
4.9
Super!
Italy: Pontine Islands
3 days - 2 nights
6 departures available
July - September
Starting from
€370
€352
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
4 departures available
September - October
Starting from
€294
Per person
4.9
Super!
Italy: Aegadian islands
7 days - 7 nights
5 departures available
August - September
Starting from
€600
Per person
4.9
Super!
Italy: Tuscany
7 days - 7 nights
2 departures available
July - August
Starting from
€870
Per person
4.3
France: French Riviera and Porquerolles
7 days - 7 nights
10 departures available
July - September
Starting from
€700
€630
Per person
4.7
Spain: The Balearic Islands
6 days - 7 nights
4 departures available
July - August
Starting from
€1,200
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 7 nights
2 departures available
July
€790
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
16180 reviews
Short sailing cruise in the Gulf of Naples
07/11/2025
Daniela D.
-
Italy
Life-changing experiences - Escape to the Pontine Islands
07/11/2025
Emanuela P.
Sailing weekend in the Pontine Islands
07/10/2025
Stefano M.
-
Italy
Experience the sea at 360 degrees? embark with us in Kos
07/9/2025
Davide M.
-
Italy
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