Windsurfing long distances with Henry Cartwright – the Journeyman.

Windsurfing long distances is a pretty niche activity. No less there are some who indulge. Henry Cartwright is doing things his own way and one of those aforementioned. Using his windsurfing kit as a vehicle Henry’s passion for journeying and touring is right on the fringe of what most windsurfers consider the sport to be. We caught up with Henry to find out more.

When and how did you first get into windsurfing?

I got into windsurfing at the age of 13. I had a go on a family longboard with a 6.1m sail and loved it immediately. I liked going (what I thought was) fast but most of all just being on the water and feeling a really powerful sensory connection to the kit, the conditions and the water.

All smiles for Henry when windsurfing.

What appeals? Why do you love it?

Windsurfing has always been a family thing for me with my brother and sister and staying down with my grandparents on Hayling so is very much associated with fun family times at Hayling Island Sailing Club. Everything about the sport appeals; to a greater exhilaration than any roller coaster while being on the sea which I would describe to any skier as being one huge wild off-piste! Windsurfing’s physicality combined with its freedom brings it into an almost spiritual realm.

Where did you do most of your sailing growing up?

I started sailing my oppy aged 8, then raced a mix of dinghies including toppers and an RS200 in my early teens around the Junior week, Mengham week, Fed week circuit. Once I discovered windsurfing that was phased out fairly rapidly although I still like dinghy sailing a lot and also sail yachts these days. All of this and the early windsurfing happened at Hayling Island Sailing Club with the occasional trip to Greece and Turkey for Sunsail holidays, Yedi Tepe in Turkey being the first time I planed on a short board! Other classic destinations like Club Vass, Dahab and Tarifa have featured since.

Essential windsurfing kit for distance and touring.

When and how did you get into destination, journey windsurfing?

Aged 15 (soon after I started planing) I drew into my geography GCSE atlas a plan to windsurf from Hayling to Penzance. At the time it was like a dream to land on the moon – totally absurd and just an escapism from school work. Then in 2007, I read about Guy Cribb windsurfing en masse from Bournemouth to Brighton and realised that people could travel on windsurf boards. In the summer of 2008 I parked my car in Brighton, got the train back to Hayling Island Sailing Club and set off to attempt my first long distance trip, making it just 2 miles to… Bracklesham on my 104 litre AHD totally unable to get out beyond the surf. There was a lot to learn, including packing kitchen scissors into my rucksack for anticipated sail repairs was perhaps not the best idea! Finally, I returned to the garden of some strangers who had kindly accommodated my kit.

In 2015 after many years of ‘normal’ windsurfing I followed Jono Dunnett’s circumnavigation of Britain and was totally captivated. Jono and I have been in correspondence since. It was in the summer of 2016 when a friend said I should visit him in Norfolk that I set off from Felixstowe on my 112 litre BIC Techno, laden with tins of tuna, to work my way up the coast! This time I was semi- successful and in true Jono style slept under the sail over the course of the 2 day trip. I was terrified throughout but absolutely loved it.

2017 was my first (unsuccessful) round Isle of Wight attempt after having completed double digit laps of Hayling that year. Again I learnt a lot rounding the Needles on a short board.

In the spring of 2019 I bought a second hand Starboard longboard which was a total gamechanger and with Mike Pringuer’s help got it down to Hayling. This was the proper start of my long distance windsurfing career and I windsurfed that board down to Penzance from Hayling over 2 weeks in 2019 and 2020, finally completing the Isle of Wight Circumnavigation in 9 hours from Hayling Island Sailing Club in 2020 as well as many other trips.

What appeals about windsurfing touring and covering distance?

Quite simply it’s the challenge and variety. There are the physical challenges and the mentalchallenges. The test of seamanship and judgement of the conditions makes it a constant – big stakes. strategical game with the elements. I like the decision making that is required; when to go and when not to go. The dynamic is always David vs Goliath where the windsurfer is naturally an underdog in the face of the sea. While it can be a battle – at its best feels like harmony.

Watch the shore dump!

How come you haven’t followed the freestyle, slalom or wave path?

Well that’s a function of being based at Hayling Island Sailing Club and (mostly) not having had a car during my windsurfing career. I used to watch Lars Petersen’s ‘Free Your Mind’ video on repeat. During my gap year job in Winchester I realised in my one hour lunch break I could walk home and back in 50 minutes and watch 10 minutes of this video – totally worth it! So my freestyle is limited to (some of) Lars’ tricks being mostly carving manoeuvres. I hope to windsurf for many years to come and avoid injury, so have generally avoided aerial tricks although I could definitely get into wave sailing.

This summer you completed a milestone England to France crossing. Tell us about the experience.

Really notable was the sheer range of conditions I sailed, from getting becalmed to 30 knots, always being on the same 6m sail! It was really great seeing parts of the coastline I didn’t know and the Beachy Head and Seven Sisters cliffs were a real highlight and totally majestic. I felt comfortable with the scale of the challenge and most scenarios, from limited landing opportunities to choppy sea states and difficult landings. Hayling Island Sailing Club has made me so accustomed to easy landings that I found the shore dump along much of the South East coast pretty testing, particularly when you have a 377 litre board, heavy rucksack and multiple bottles of water strapped to the board! One bad landing was at the seemingly benign shingle Elmer Beach in West Sussex where I managed to snap my fin clean in half. Not ideal when you are in the middle of nowhere. Otherwise, I felt my experience in managing my fear and being in open water around ships had been helped enormously by my 15+ unsupported crossings to the Isle of Wight. People seem to be enjoying my YouTube series and it’s very satisfying to hear people are returning to windsurfing having enjoyed the videos which can be found at

Any other big windsurfing journeys planned in the pipeline?

Watch this space…

What are your key tips for anyone fancying some of the same?

Do lots of smaller trips before putting yourself at risk of danger. There are many great trips in Poole Langstone or Chichester Harbours. Otherwise, they say you are only as good as your last performance but in long distance windsurfing I say you are only as good as your current one. That is to say, I am no better qualified than anyone else. The sea does not care what you may have previously achieved. It will judge you based on your decisions right now. I would suggest you get a longboard with a daggerboard so that you can get upwind and sail off the plane and also ensure you carry appropriate safety devices such as mobile phones, EPIRB, VHF radio and GPS trackers and of course tell someone where you are going or ask them to track you. Do not risk kit failure so you need well serviced kit. I had my board separate from my rig 3 miles off Sidmouth due to a faulty pin. It was truly a miracle that I managed to reconnect the two while being in the water.

Spot the windsurfing board!

Talk us through your most used windsurfing kit.

My most used kit is my new 377 litre Starboard Phantom. I bought it last year because the slot flusher on my old longboard kept coming loose. This is a plastic strip on the underside of the board over the centreboard slot which can present real danger if detached in an offshore wind. I have a nice collection of Ezzy sails from 6.0m to 7.5m and use my 7m most but plumped for the 6.0m for journeying from Hayling to France as it was mostly downwind and I really didn’t want to be overpowered mid-Channel.

Any further thoughts on windsurfing?

While it’s of course the most beautiful sport there are some obstacles that windsurfing needs to overcome. Firstly, it is difficult so needs to be fun at the beginning. Something I have learnt from making videos – otherwise people switch off. Secondly, it needs to overcome the ‘car’ issue. Fewer and fewer young people have cars so hire kit needs to be accessible. Thirdly is the wind – well that’s inherent to the sport. Longboards and foiling address that and we are in a much better position than 30 or 40 years ago with better forecasts. I would love to see more people come into the sport and hope in a very small way to be showing people what can be done in the world of windsurfing!

This article was first published in the autumn 2023 digital issue of Windsurfing UK which you can read here.

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