Edoardo G.
review about One way from Venice, Montenegro, Syracuse and Trapani. Possibility to book 1 week. June 2017
Great commander
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 you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Adventure & Activity sailing holidays & skippered tours
29 reviews
Massimiliano P.
review about Nordic Adventure - Stage 1: from Tromsø to Bodø (ALL INCLUSIVE) June 2022
Good morning, the premise of this holiday for me was to visit places unknown to me and pristine and I must say that I got the result. Nanni has proved to be a person with very high competence and great culture. Hearing him talk about his travels was fascinating. The only negative note I found in the boat, not for the seniority but for the hygienic conditions that left something to be desired, in addition to the persistent smell of diesel. However, I was overwhelmed by the experience I was preparing to have and the fact that I was the only passenger.
Luana R.
review about The Way of the Lion - From Thessaloniki to Greece to Istanbul, Turkey August 2019
August 2019
Thessaloniki-Istanbul
Fabrizio greeted us on board with a big smile.
The destination, Istanbul, is far away: two weeks of navigation on a sea that is anything but easy. However, Fabrizio's competence and scrupulousness has always made us feel in total safety.
The boat is splendid and was already ready for the Meltemi (with armed torment) but when the wind is too much (50 knots on the quay) you do not risk, you stay in port, at the cost of having to give up the bath anchorages.
The Aegean in August is not for holiday cruise passengers, it is for adventurous, but responsible, sailors.
Certainly I would be more than ready to embark again with Fabrizio, indeed, I would have stayed there more than willingly for the return (finally with wind in favor), but the holidays end, hopefully next year!
Bruno C.
review about The Scilly Islands from southern Brittany June 2019
The skipper: Pedagogue and admirable sailor as in September 2018, lets us bar, and maneuver, helped by another skipper, Fabrice, permanently ds the cockpit, patient, vigilant and very pedagogue also.
6 ds the boat dt 2 skippers and 2 experienced sailors .the Scilly project could not be realized, weather compatibility ... too bad that the initial project does not talk about plan B for the 14 days planned (even for some not to take the trip). Not so much the modification of the project as the way it could be done. South Brittany, Patrick's "garden" is a splendid country. Thank you Patrick and Fabrice
Jean Francois M.
review about Transatlantic, experience of a lifetime! From the Antilles to the Azores April 2019
Fabulous nautical and human experience made possible by Hervé. An extremely competent skipper, patient and pedagogue who quickly familiarized us with driving a 50 feet cut for racing. Routing, weather, astronomy, sextant, splices, repairs... are all terrains that could be approached during this crossing, all in an excellent atmosphere.
Ausra G.
review about "Porto Azzurro CUP Regatta!" - Winter Championship February 2019
A beautiful experience.
Francesca R.
review about Two-week adventure to discover the Costa Smeralda and Elba August 2018
Marco is an experienced and super reliable skipper, he has studied, elaborated and respected the itinerary presented in the program, to give us dives and breathtaking views! His competence, sympathy and seriousness have made the holiday serene even in the face of any unforeseen events.
The people we met were a pleasant surprise, so much so that this holiday was full of music, laughter and Campari! :-)
So I recommend this type of holiday to all those who are afraid of getting bored on the boat! :-)
Oscar C.
review about Discover Lofoten August 2018
I did with Marco the tour of Lofoten in August.
Punctual, very helpful and precise for the pre-rociera agreements. Great skipper, from safety. Excellent cook, knows how to enhance what is available on site (fish). The boat is comfortable - only 2 cabins with very comfortable berths. The boat has its years but it is a real pleasure to lead it and gives a lot of security even with sustained winds. Little electronic but very reactive and fast., for those who like to feel the wind and observe the sails. gives a lot of satisfaction. Consiglato from all points of view.
Patrizia S.
review about Eco-Tour of the Aeolian Islands August 2018
Wonderful holiday in a beautiful and comfortable boat for 6 people. Franco was kind, helpful and sociable with all of us. For those who want to get off and visit the islands a tip: The travel program in August must be organized in detail to avoid not finding a place to moor, full restaurants or exhausted ground services.
Mariella M.
review about Offshore sailing on a Swan 65 from Sicily to Patras July 2018
This flight from Syracuse to Kefalonia in just 36 hours is unforgettable! Unforgettable the starry skies of the Mediterranean, the milky way and the moon contemplated in this offshore navigation on the oldest route to Greece.
Pieter, own and skipper, proved to be skilled, experienced and as his friend Rob tireless sailors.
Pieter has shown surprising resource in managing this navigation that in some moments has turned in a real adventure. And despite the effort required by the shifts of uninterrupted navigation, in my night of seakness, Pieter has found away to nurture me carefully. The boat proved to be an unsurpassable vessel! Enjoy!
Luc D.
review about Viking Cruise in the Norway's Fjords April 2018
Paul is a character! who knows the Stavanger region (Islands and Fjords) well. His boat is very comfortable and safe. Good atmosphere on board with the 2 Swiss teammates Hugo and Florian with the surprise of Elizée Joy Montana made it a very nice cruise.
The boat lacked preparation, we lost a good day, the storage is not Paul's fort.
Paul needs to improve his skipper skills for other sailing and weather conditions.
Giovanni A.
review about Transat: Canary Islands - Cape Verde one way November 2017
Professional skipper in every situation. It was a pleasure to cross a piece of the Atlantic with Francesco. He has always transmitted to the crew safety and his passion for the sea!
Alessandra I.
review about The commerial routes between Spain and Sicily April 2017
Stephane is not only an outstanding sailing master, but he is a truly nice and interesting person, a lovely shipowner who makes you feel at home since from the very first beginning. He is very attentive to the needs of his crew, and able to transmit its passion for sailing and life at sea. And he has a wonderful boat, seaworthy and fast, and not just because is a Baltic (already a guarantee in terms of quality and safety) but thanks to the way and love Stephane takes care of it. It's very spacious and confortable with amenities of all kind. I spent more than 2 weeks with him and his friendly crew and was one of the best sailing trip I have ever done (and luckily I had many). We sailed more than 1,000 miles, experienced different kind of weather, wind and sea conditions, sailed night watching under clear starry skies, anchored in beautiful bays, had lot of fun, delicious meals, wines and talks, and so many other lovely memories to tell. I do really had a great time, thanks Stephane!
Robert M.
review about The Long Range. From Malta to Varazze One Shot October 2017
The trip was great, very nice spots we visited and a good care of delicious dinners.
Thanks,
Fabio en other crew members
Noemi A.
review about Discover The Sea of Cortez ! August 2017
The holiday with Nicolas was a unique experience. He is a great captain with a lot of experience, very knowledgeable in both navigation and safety. The boat is a beautiful piece of great German engineering. It is very large and roomy as well. He is always on the lookout to accomodate your needs as possible. He turned out to be a great traveling companion. Serious enough when he had to be and ready to laugh when he was relaxed. The place where he took us is beautiful. The above water surrounding mountains landscape of both islands and mainland where gorgeous as well as the beautiful blue, emerald green and warm water with a variety of sea life. But above all, It is a place that for many still unknown and ready to be discovered.
Paradigme 2.0 is the perfect boat for your sailing adventure and discovering experience. Godspeed!
Ann R.
review about Sailing from Lofoten to Alesund, One way August 2017
Guy and the whole crew made this a very enjoyable and memorable trip. He was confident and friendly in all areas. He made the trip relaxing and fun. I would highly recommend the boat and crew to family and friends.
Lamine M.
review about Dream Cruise: Cannes - Corsica - North Sardenia, One Way July 2017
Very pleasant stay in the company of Stan and his small family, accommodating and friendly skipper. Beautiful sailing experience, breathtaking landscapes. Unforgettable moments of sharing and relaxation. Excellent if you want to escape the hordes of tourists and want to discover small coves full of charm.
Massimo G.
review about Sailing and adventure at Azores July 2017
Professional skipper, very prepared, available with the participants, I recommend it!
Omar D.
review about Summer 2017: the dream of sailing along the coasts of Zante, Kefalonia and Ithaca on board the Moana May 2017
Fantastic experience both for the Boat (to fall in love with) and for the Skipper who has been able to amalgamate a heterogeneous group and pull out of the cylinder an unforgettable holiday.
Needless to say, the sea, the bays, the coves and the beaches were fantastic but the TOP was to live the boat like this: all together in common (there were no couples) and create a close-knit group; It was a fantastic experience and I hope to set foot on board the Moana60 very soon; I recommend Moana to those who leave alone and those who like to experience the sea and the boat. A great start if you do not have experience on the boat if instead you know the rudiments Nicola will make you mount the Adreanalina!!! See you soon Nicola!
Robert M.
review about Rolex Cup Giraglia...a regatta for real sailors! - All Inclusive June 2017
Good organized trip, with nice meals and friendly crewmembers.
Customer Support
Would you like some support using the platform? We've (almost) always got the answers!
Call us at +44 20351 44220
Check out our Help page
Can't find the perfect holiday for you?
Use our free holiday concierge tool - and let us find your dream sailing experience for you!
Let's find it together!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.