Holidays and cruises on sailboats with organized activities.
Do you love to relax but also need to stay active or pursue your greatest passions? On a sailboat, you can enjoy a week or weekend of sailing and sea, combining activities such as trekking, yoga, snorkeling, and even gastronomic tastings.
17
experiences
17
experiences
5.0
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
August
€1,430
€1,287
Per person
5.0
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
July
€870
€790
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
3 departures available
July - August
Starting from
€135
Per person
5.0
Super!
Italy: Southern Sardinia
5 days - 6 nights
2 departures available
October - November
€1,450
Per person
5.0
Greece: Saronic Islands and Athens area
6 days - 7 nights
12 departures available
July - October
Starting from
€990
Per person
5.0
Africa: Egypt & Red Sea
6 days - 6 nights
One departure available
August
€795
Per person
Greece: Cyclades
7 days - 7 nights
2 departures available
September - October
Starting from
€997
€798
Per person
Greece: Cyclades
7 days - 7 nights
3 departures available
August - October
Starting from
€1,020
€816
Per person
France: Corsica
7 days - 7 nights
2 departures available
July - August
€1,100
Per person
5.0
Italy: Tuscany
6 days - 7 nights
One departure available
August
€1,559
Per person
4.5
Italy: Northern Sardinia
7 days - 7 nights
One departure available
July - August
€1,250
Per person
Croatia: Kornati Islands
7 days - 7 nights
2 departures available
July - August
€700
€630
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 - Holidays and cruises on sailboats with organized activities.
1301 reviews
Weekend a Capraia, trekking e natura
07/5/2025
Sonia G.
-
Italy
Weekend a Capraia, trekking e natura
06/22/2025
Leonardo D.
-
Italy
Weekend a Capraia, trekking e natura
06/18/2025
Giovanni N.
-
Italy
Weekend a Capraia, trekking e natura
06/10/2025
Kristian G.
-
Italy
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