If you cast your mind back a little more than a decade ago, when Instagram had barely come on the scene, TikTok was the sound a clock made, and XOverland had only uploaded a handful of videos to YouTube, you may remember a time when blogs reigned supreme. As my own long-term travel ambitions began to gel in the early twenty-teens, I voraciously consumed many overland adventure blogs looking for inspiration and maybe even a small dose of confidence. One stood head and shoulders above the rest: Desk to Glory. In those days, Richard and Ashley Giordano’s chronicle of their 2013-2015 Pan-American Highway journey was required reading for all overlanders, even the armchair ones in Montana, and I never missed a post.
Richard and Ashley Giordano, aka Desk to Glory, reach land’s end in Ushuaia, June 2015.
These intrepid Canadians with their little red Toyota pickup were curious, open-hearted, empathetic, real. They traveled mindfully, soaking up all their best escapades, reflecting deeply on their experiences, and never shying away from sharing their hardships. In short, Rich and Ash were the kinds of travelers I aspired to be. Of course, it didn’t hurt that they could take incredible photographs and write vividly and with conviction. The Pan-American posts still read as fresh today as they did ten years ago. Their adventures made me think, “Hey, maybe I can do that!” Just a month after Desk to Glory wrapped up their South American tour, I found myself behind the wheel of a Toyota HiLux, GPS locked in for Namibia’s Sossusvlei dunes. I suspect I wasn’t the only newly-minted international overlander drawn in Richard and Ashley’s wake.
Times change and so do platforms, but the Giordanos are still at it: traveling with intention and inviting us into their lives on the road. They also continue to ask the big questions. “Why We Overland” is Desk to Glory’s latest pursuit of far horizons and their own answers to those questions. Maybe you’ll find some of your own in their journeys as well.
Yes, that’s Scotland.
Follow Richard and Ashley as they step into full-time life in their 2008 Toyota Tundra, discovering what it means to travel overland through the United Kingdom, Europe, Northern Africa, and beyond.
New episodes will be released every Thursday on the Expedition Portal YouTube channel, beginning with Episode 1 – Canada | Why We Overland: To Build a Home, which went live yesterday.
Find Richard and Ashley on Instagram in between episodes:
@desktoglory
@desktoglory_ash
Epsiode 1 – CANADA | Why We Overland: To Build A Home
In 2013, Richard and Ashley drove their 1990 Toyota Pickup 45,000 kilometers from Vancouver, BC to Ushuaia, Argentina. Since their return in 2016, they’ve hustled to make remote work and long-term travel a possibility, subsequently building a “new” Toyota for these upcoming adventures. Join Richard and Ashley as they build their 2008 Toyota Tundra, ship it across the pond to England, and start the next phase of their overland travels.
Episode 2 – MALTA | Why We Overland: To Learn About Ourselves
Waiting for their Tundra to arrive in the UK, Richard and Ashley visit the tiny island nation of Malta, diving deep into Richard’s family history. Debuts December 11, 2025.
Episode 3 – ENGLAND | Why We Overland: To Step Back In Time
After picking up their Tundra in the UK, Richard and Ashley head straight for Scotland—but not without first getting a taste of British history. Debuts December 18, 2025.
Episode 4 – SCOTLAND | Why We Overland: To Feel Remote
Richard and Ashley search for remote regions of Scotland in Skye and the Outer Hebrides. After slowing their pace, they are able to meet with local crofters on the far reaches of the islands to learn about the centuries-old small-scale food production system. A secret tip sends them to a cliffside dwelling for a wild night under the stars. Debuts December 25, 2025.
Episode 5 – SPAIN | Why We Overland: To Eat, A Lot
There are many ways to learn about a region. Richard and Ashley learn more about Spain by staying in one area as long as possible, focusing their time in Asturias and Basque Country, and eating a wide variety of food, trekking into the mountains, and spending time with the people that live there. Debuts January 1, 2026.
Episode 6 – MOROCCO PART 1 | Why We Overland: To Spend Time in the Desert
Richard and Ashley take the ferry to Morocco with the intention of heading straight to the desert. The 30-minute ferry from Spain is like a rocketship to Mars. Debuts January 8, 2026.
Watch more:
New Video Series from Bound for Nowhere
Roam Overlanding Launches 7-part Africa Overland Series
Gon Dirtin’ Debuts “Gon Cookin’,” a 6-Part Food and Travel Series
Images: Richard Giordano, Ashley Giordano
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