Instructors Are Key

Your instructor will make or break your sailing course. A jaded, salty instructor does not make for an awesome week, especially if you’re in your 20s or 30s. For that reason we have a unique selection method for our instructors. Every instructor with Sailing Virgins is not just an accredited instructor with one or more of the global sailing associations, but must have the following:
  • Minimum two ocean crossings. Our guys know their offshore sailing;
  • Minimum two seasons working with The Yacht Week. Our guys know how to have fun;
  • Minimum two seasons working together. The bond between instructors is strong and the banter is real.

Working as skippers, lead skippers, route managers and instructors with The Yacht Week and The BucketLust forms a bond that translates into the awesome culture everyone who has sailed with us talks about. For some other reasons to choose us, check out this page.

James Kell, Founder

James started sailing as a boy with his family in New Zealand.  The Bay of Islands contains fantastic sailing grounds and is an excellent nursery for a sailor.  Fast forward a few years, cross the Atlantic a few times, and James is now running things at Sailing Virgins.

Leaving corporate life in 2012, James spent a few summers working for legendary (and, in the best way, notorious) sailing events company The Yacht Week, including as Route Manager of Greece in 2015.  James holds senior instructor qualifications with all of the top three global sailing organisations: ASA (Advanced Coastal Skipper and Catamaran Instructor), IYT and RYA (Yachtmaster Instructor).


“I love sailing and get a kick out of sharing what I know with people who are keen to learn.”

James Kell, confirmed tree-hugger, callsign “Carpe Diem”.

Jack Karger, Senior Instructor

Hailing from the not-at-all-coastal town of Bordertown, South Australia, Jack grew a healthy obsession with BMX riding at a young age. His sailing started when his cousin Riley invited him to help sail a boat he had just bought called La Vagabonde. La Vagabonde happened to be moored a few boats away from Libertas (captained by James) in Cape Verde as both boats prepared to cross the Atlantic. They all caught up again on the other side, with both crews literally running into each other in Road Town, BVI. La Vagabonde has since become a Youtube sensation, with over 300K subscribers, and Libertas is the flagship of Sailing Virgins fleet. Following the second meetup, James and Jack spent several weeks in the Caribbean sailing together. Jack subsequently worked several European and Caribbean seasons with The Yacht Week as skipper, lead skipper and ultimately Route Manager, as well as some transats under his belt. Jack holds his Yachtmaster Instructor certificate from the Royal Yachting Association and loves to teach catamaran hacks.

“I reckon this is champagne sailing right now…”

Jack, call sign “Just The Tip”, sharing the love.

Rupert Covell, Sailing Instructor

This is Rupert. He’s from Yorkshire. He’s a special kid our Rupert. Like all Sailing Virgins instructors, Rupert has spent a few seasons working as a skipper for The Yacht Week. More recently he and a few partners started The BucketLust: a week of sailing plus the odd party every now and then. Rupert hails from the UK and holds instructor qualifications (including catamaran endorsement) with the American Sailing Association.

rupert covell

“I wish I was an Australian”

This is what happens when your quote is written by your boss. Rupert Covell, callsign “Maverick”.

Image thanks to Roam Travel PR

Kirill Osipenko, Sailing Instructor

We’re all citizens of the world, but Kirill really takes the cake. Born in Ukraine, Kirill moved to Israel as a boy and grew up there. Army time did little to his predilection for long curly hair, but it did introduce him to his beloved capoeira dance. This came in handy after one ocean crossing, when pirates attempted to board his boat in Brazil. Music on, capoeira moves busted out, pirates gone. Not only a great sailor but possibly the most positive person you will ever meet; spending a week on a boat with Kirill is a treat.


Image thanks Raphael Picas and The Yacht Week

“Currently enjoying life 

Kirill’s Facebook Introduction, and life philosophy

Hugo Pulse, Sailing Instructor

Hugo is the real deal. The last time this Frenchman crossed the Atlantic in his 26′ monohull, he took the well-worn trade route from south of Gibraltar to pick up the easterly trade winds and enjoy the expected 20 day crossing. The easterly winds turned to rare westerlies for the first week, which extended his trip by ten days. We met up with him in Martinique, on the Caribbean side, and asked him how it was. “Oh it was fine” was his classic, no-big-deal response. He rationed to 1/2 a gallon of water per day for everything (including drinking water), and just went minimalist for the crossing. No issues. Hugo has his own Youtube Channel called the Sailing Frenchman, with 15,000 subscribers. If you get Hugo as your instructor, you’re in for a treat.
hugo pulse
Hugo Pulse (image thanks Anne Beaugé)
“You need to sail a boat like you bake a baguette.”
Hugo Pulse, giving epithets that leave us confused, callsign “Sailing Frenchman”

Thanks Michael Vanarey for half the shots on this site.  Vanarey is awesome!

Thanks Céline Freixe for most of the videos that have been produced so far. We ❤️ Céline.