‘Being offline and Trump free has been a blessing,’ says solo sailor Matt Woodside of going off-grid for the 2026 Golden Globe Race
Self-proclaimed 'sailing luddite' and solo sailor Matt Woodside is gearing up to sail around the world solo, nonstop, and unassisted using only traditional navigation techniques. Here's how he's preparing for the 2026 Golden Globe Race.
Matt Woodside can’t come to the phone right now.
He’s busy munching miles, pressing towards the East Coast of the United States on his Cape George 36, Tipi Haere, drawing closer to the start of the Golden Globe Race.
Come September, he’ll take on what has been called ‘the Voyage of Madmen’ and ‘the Loneliest Race in the World’: sailing around the world solo, nonstop, and unassisted using only traditional navigation techniques.
For this self proclaimed ‘sailing luddite,’ the limited onboard technology is part of the appeal.
‘Being offline and Trump free has been a blessing,’ he says of being out of reach of modern communication.
Photo by Matt Woodside
The Golden Globe Race bug bit him early.
‘The crazy story surrounding the 1968 Golden Globe race left quite an impression on me as a young lad,’ he says. He would’ve been a Sea Scout in Invercargill, New Zealand around that time.
He considered entering in 2022, but life ‘has a habit of getting in the way sometimes.’
Now, he’s grateful to the organisers for ‘putting on this race series and getting me off the dime,’ and for keeping the spirit of retro racing spirit alive.
Woodside has been preparing for the challenge of a solo circumnavigation by ‘racking up some serious mileage in the boat.’
He’ll be off grid until May, when he’ll stop for final boat preparations before heading to the starting line in Les Sables d’Olonne. We were last in touch when he was in the Falklands, waiting for the winds to change. He signed off, ‘Off to see some penguins after breakfast.’
Since July 2025, he and Tipi Haere have sailed from Pt. Townsend, Washington to San Francisco, then to San Diego, Nuku Hiva in the Marquesas, Samoa, and from Fiji to New Zealand. From New Zealand, he rounded the dreaded Cape Horn and headed to the Falkland Islands.
‘It has been both humbling and edifying,’ he says of the voyage. ‘I have learned a lot about the boat and how to fix things that I break. And it’s wicked good exercise.’
Photo by Matt Woodside
Woodside has owned Tipi Haere since 2010. He was working in Seattle at the time (he spent almost 30 years in the Navy), and wanted a bluewater sailboat that he could also live on. He stumbled across this one in Puget Sound, Bainbridge Island.
‘It was love at first sight: beautiful lines, well built, and with a lovely interior. And what a fine sailer she is. The fact that she had a Te Reo name was the icing on the cake.’ (Woodside did part of his schooling in New Zealand)
‘I feel most fortunate in my choice, particularly as her home yard, Cape George Marine Works, is still in operation up in Pt. Townsend, WA.’
Since Woodside acquired her, Tipi Haere has been in and out of the Pt. Townsend yard three times over.
Her latest stint was in June 2025, when she went through a major refit including all new mast and rigging, new and beefier chain plates, kranze iron, and stanchions. The cockpit and cabin top were also rebuilt with new dorade boxes.
‘Pt. Townsend has such a vibrant maritime culture that I have been able to get everything needed for this campaign: a new mast and rigging, sails, and engine work from local businesses,’ Woodside says.
‘The support and encouragement that I have received from friends across several communities and family has been incredibly gratifying and humbling.’
Photo by Matt Woodside
With over a decade and a half’s experience on Tipi Haere, Woodside says he’s particularly pleased with how she handles heavy weather.
‘The Cape George is extremely well balanced and heaves to nicely. In a fast moving storm with a light sea state, she is even comfortable lying a-hull.’
The boat has already earned a GGR pedigree; Kirsten Neuschäfer won the 2022 race on her Cape George Cutter, Minnehaha. 2026 entrants Stephen Wraith and Henry Wotton (Privateer) also intend to sail on Cape George 36s.
Over the years, Woodside added mounting plates t0 the transom to mount a Jordan series drogue, a sea anchor, and warps.
The important thing, he stresses, is to have options, and to be mindful of how much rest and preparation is required to complete every small task when sailing single-handed.
‘People don’t realise that most everything takes longer when you’re sailing alone. For example, I eat well, but prepping, cooking, and cleaning up are not as simple as they are ashore. Sail changes, maintenance, the list goes on and on. Celestial navigation is pretty time intensive.’
Woodside first learned the technique when he was in the US Navy, using a periscopic aviation sextant rather than a nautical sextant.
Thankfully, ‘the computations and plotting are the same. It’s all coming back to me.’
Kirsten Neuschäfer’s winning Cape George Cutter Minnehaha, designed by Cecil Lange, was built in the Cape George yard in Port Townsend, Washington and launched in 1988. Photo by D&JJ/GGR 2022.
He’s looking forward to arriving in Les Sables d’Olonne, ‘to meeting everyone and brushing up against the impressive French sailing culture that has had such success in my lifetime.’
But there are still a few hurdles left before the start.
Woodside worries about getting to September ‘with all of the Notice of Race requirements completed. It has been a bit of a moving target.’ He still needs to get his SSB (single sideband radio) license, and take some required classes.
While he’s rearing to go, he’s aware of the potential risks of undertaking the Golden Globe Race.
‘This is truly a marathon and these are older boats that we are pushing,’ he says. ‘I’m pretty competitive by nature, but you have to finish to win.’
Quick facts: Matt Woodside / Tipi Haere
Sail Plan?
Genoa, Yankee, staysail, mainsail, storm trysail, storm staysail, and a couple of asymmetric spinnakers. That’s what I’m thinking right now.
Furler or hank on?
She has a cutter rig. The foresail, a Yankee or Genoa is on a furler and the staysail is hanked on.
Self-steering set up?
A mighty Monitor. I have used this particular unit since 2014 and will give it a full reconditioning before the start.
Antifouling?
Seahawk CUKote
Sailing Inspirations:
I’m a reader. Slocum, Chichester, Moitessier, and any number of earlier out of print sailors.
Three unexpected items you’ll take onboard:
- There are some amazing food options out there these days. My current go to is Indian food from the Cumin Club
- I have a pile of books, but am tending to the classics from the Iliad, to Shakespeare, to the Shahnameh
- And I have my grandson Levi’s spirit animal with me!
Woodside’s grandson Levi gave him this talisman. Photo by Matt Woodside
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The post ‘Being offline and Trump free has been a blessing,’ says solo sailor Matt Woodside of going off-grid for the 2026 Golden Globe Race appeared first on Yachting Monthly.