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.
168
experiences
168
experiences
5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
One departure available
September
€790
Per person
5.0
Super!
Italy: Liguria
2 days - 1 night
One departure available
September
€225
Per person
5.0
Super!
Italy: Southern Sardinia
7 days - 7 nights
4 departures available
September - October
€990
Per person
4.8
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€420
Per person
4.7
Italy: Naples & Amalfi Coast
3 days - 3 nights
One departure available
September
€452
Per person
4.3
Spain: Andalusia
9 days - 9 nights
One departure available
October - November
€470
Per person
5.0
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September
€900
Per person
4.8
Italy: Tuscany
2 days - 2 nights
2 departures available
October - November
€300
Per person
5.0
Italy: Tuscany
3 days - 2 nights
2 departures available
September
Starting from
€300
€270
Per person
4.8
Italy: Aegadian islands
7 days - 7 nights
One departure available
September
€600
€570
Per person
4.7
Spain: The Balearic Islands
6 days - 7 nights
3 departures available
September - October
Starting from
€600
Per person
Greece: Cyclades
7 days - 7 nights
One departure available
October
€580
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
17477 reviews
Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation
09/17/2025
Mauro Z.
-
Italy
Weekend at the Pontine aboard a splendid 16-meter sailboat
09/17/2025
Giulia E.
-
Italy
Egadi paradise for sailing and snorkeling
09/17/2025
Vicky H.
-
Belgium
A week in the Aeolian Islands - 6 islands in seven days
09/17/2025
Giuseppe I.
-
Italy
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