
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.
410
experiences

4.9
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
July - September
€400
Per person

4.6
Italy: Northern Sardinia
6 days - 7 nights
6 departures available
July - October
Starting from
€650
€585
Per person

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

4.8
Super!
Italy: Tuscany
4 days - 3 nights
4 departures available
August - September
Starting from
€400
€360
Per person

5.0
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
€1,020
Per person

4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
August - September
Starting from
€600
€540
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
September
€650
Per person

5.0
Super!
Croatia: Istrian peninsula
7 days - 7 nights
One departure available
August
€649
Per person

5.0
Italy: Southern Sardinia
6 days - 7 nights
7 departures available
August - September
Starting from
€790
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
€585
€527
Per person

5.0
Super!
Italy: Tuscany
14 days - 14 nights
One departure available
August
€1,700
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
September
€950
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
18165 reviews
A week in the Aeolian Islands - 6 islands in seven days
07/23/2026
Deborah T.
-
IT
Week end in Costa Azzurra
07/23/2026
Isabella R.
-
IT
The most spectacular islands of the Cyclades: from Athens to Milos
07/23/2026
Frank W.
-
DE
Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea
07/22/2026
chiara a.
-
IT
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