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Adventure & Activity sailing holidays & skippered tours

Unusual adventures at sea on board an exceptional cruise on the sailing boat or catamaran of a passionate skipper. Enjoy the sensations and come back with a lot of memories!



Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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 - Adventure & Activity sailing holidays & skippered tours

41 reviews

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Cape Horn and Patagonian glaciers cruise 15 days / 14 nights


Sandro S.



Bellissimo viaggio attorno le isole della Terra del Fuoco, nella natura selvaggia e paesaggi mozzafiato. Laurent é un preparatissimo skipper che vi guiderà in questa avventura fin sotto i più bei ghiacciai della Patagonia
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Sail west and south coast of Norway and discover the fjords and archipeligo


Jeannou B.



Sailing from Bergen to Oslo with Steinar was a great experience! Besides being a good cook, he has many stories to tell and likes sharing them :). He is also a man with a lot of sailing expertise and knows what he is doing. Would defenitely recommend sailing with him!
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Islands at the edge of the world


Enrico M.



Una vacanza semplicemente meravigliosa, guidata da uno skipper premuroso e squisito sotto ogni punto di vista, su una barca che fa rimpiangere la direzione presa dai cantieri nautici nei gli ultimi 30 anni, in un ambiente che spesso ci ha lasciato senza parole. Marco e Britta vivono a Vannoya, una di queste isole ai confini del mondo che abbiamo avuto la possibilità di visitare, e riescono a condividere con i loro ospiti tutto il loro entusiasmo per questi luoghi. Non riesco ad immaginare guide migliori! Un piccolo avvertimento per chi pensa di intraprendere questo viaggio: avrete voglia di ritornare a trovare nuovi amici, di rimettere le mani sulla ruota del timone di Cadeau, di visitare l’accogliente Haus of Books. Grazie ancora Britta e Marco, arrivederci a presto!
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In the footpath of the Vikings - Bergen - Shetland - Orkney Islands


paolo m.

Ottimo skipper e bravissima persona. Molto consigliato

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6 reasons to choose Sailsquare for your next holiday:

  • If you have a desire to explore the world, push boundaries and discover new lands
  • If you want to go on one of those trips that will stay in your heart forever, such as sailing across the Atlantic
  • If you want to get away from mass tourism, off the beaten track, you can for example go to discover "virgin" places such as Antarctica, Greenland...
  • If you are looking for pure adrenaline, in which case you can opt for a cruise combined with an extreme sport
  • If you feel like disconnecting from the digital world, contemplating the wonders of nature, living with it, rather than with your smartphone
  • If you want to share with other people this unusual adventure

Go on an adventure without further delay

You don't have to be an old sea dog to achieve incredible sailing adventure holidays. Crossing the Atlantic, polar expeditions, exploring fjords and glaciers, discovering deserted atolls, whale safaris... Here you will find adventure cruises in sailing boats organised by professional skippers all over the world. You will find here cruises in wide open spaces, sport cruises, and long duration cruises.

Everything you need to know before going on an adventure cruise:

What's the best time of year for an out-of-this-world adventure:

Every time is a good time to satisfy a thirst for adventure. There are some in all the seas of the world, so it is possible for you to go in winter as well as in summer!

Adventure cruises: how much do they cost?

Adventure trips are often one-week or longer trips, naturally the longer the trip the more expensive it will be. Exceptional places are also more expensive. However you can find exceptional adventures from as little as €800.

How old are the people who take part in adventure holidays?

There are adventures for all profiles. If you are looking for a trip that is out of the ordinary, whether you are a family, a group of friends, a couple or a solo traveller, you will find an experience that suits you!

The best destinations for an out of this world holiday

There are adventures all over the world, to suit all budgets and tastes:

  • Grenadines Kitesurfing and Adventure Cruise: a trip to discover the best kitesurfing spots in the Grenadines for maximum thrills.
  • Glacier adventure in Patagonia: sailing through glaciers and rounding Cape Horn is quite a symbol for travellers, a pre, wild and sublime adventure.
  • Transatlantic towards Martinique: sailing in the open sea is an exceptional adventure for sailing enthusiasts.
  • Sailing course in Canada: go and perfect your sailing skills in the middle of a unique landscape, the east coast and the islands of Canada.

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