How Do You Even Begin to Plan a Trip Like This?

The short answer? A lot of research—and a healthy partnership between one person who dreams big and another who grounds those dreams into a workable itinerary. I bet you can guess which one of us is which! I’m definitely the ideas person, and Gary is all about logistics. Together, we’ve planned this seven-month adventure using a mix of old-school spreadsheets, an app we now can’t live without, and the incredible experiences shared by other travellers online.

The App That Changed the Way We Travel Plan

Yes, we still love a good Excel spreadsheet, but for a trip with so many moving parts—especially one involving road trips, flights, trains, and cruises—we needed something smarter. Enter Wanderlog. It’s a paid app, but worth every cent. It helped us map distances in places like Iceland (a country that looks small until you realise how long it takes to drive around it!), identify must-see attractions, and book accommodation along the route. Iceland’s rugged beauty really called to us, and we wanted to make the most of it without spending half the time in the car trying to figure out where we were going to sleep next.

Planes, Trains, Automobiles… and a Cruise!

One of our musts was cruising the Norwegian coast. After loving our Alaska cruise a few years back, we were keen to experience the Arctic Circle from the water—especially after catching the Northern Lights in Sweden in 2023. This time, we’ll follow the midnight sun north before catching the train south through Norway and into continental Europe.

We also grabbed a Eurail Global Pass during a rare 25% off sale. It gave us six weeks of first-class rail travel, perfect for our plan to cross Northern Europe by train. After Bergen, we head to Copenhagen, then zigzag through the region, avoiding the peak of European summer holidays by timing our visits to England, Scotland, and Ireland during August.

The 90-Day Rule & A Surprise EU Passport

There was a bit of a hiccup early on: between us we’re Australian and British citizens, which means we’re subject to the 90 days in 180 days Schengen rule. We thought my Italian heritage might help, but Italy had changed its citizenship laws, which closed that door. Fortunately, Gary ended up securing an Irish EU passport, which gave us the freedom to stay longer—and that changed everything. It also meant we could postpone the second half of our Europe itinerary until we had confirmation of that passport.

But what if we couldn’t stay in Europe? We needed a Plan B.

From Europe to South America: A Bold Detour

If this really is our trip of a lifetime, we didn’t want to play it safe. We decided that if we had to leave Europe after 90 days, we’d make it count. South America had always been high on our bucket list, especially Machu Picchu and Chile, so we began researching tours. Safety was a top priority, and since we’re unfamiliar with the region, a small group tour felt right. We settled on a 25-day Inspiring Vacations tour that hits all the major spots except Chile, which we’ll explore on our own in December before flying back to Australia.

We haven’t locked everything in yet—some train seat reservations and accommodations are still pending. And figuring out how to coordinate arrival and departure times with Airbnbs (that often don’t store luggage) has made us grateful for another travel lifesaver: LuggageHero, an app that helps you find short-term luggage storage around the world.

Learning from Others & Letting the Journey Evolve

So much of this journey was shaped by listening to other people’s stories—Utube videos, Facebook travel groups, blog posts. One post about the wine regions of France totally changed our timeline. What started as a two-week plan in France grew into four weeks, thanks in large part to a utuber named Vince (and his passion for vino). We’ll be following several wine trails, mostly based in smaller towns rather than big cities, and can’t wait to explore these lesser-known gems.

Packing for a Trip Like This: Not for the Faint of Heart

Packing has been one of the hardest parts—trying to fit for both hot and cold climates, stay under airline luggage limits, and be nimble enough for train travel and cobblestones. After three different bags (including a hybrid backpack from Eagle Creek and a lightweight North Face duffle), I finally settled on the Patagonia Rolling Duffel 100L. It’s spacious, durable, and just light enough. Gary went for the North Face Rolling Thunder 95L—a beast of a bag at 5kg empty but incredibly tough.

I had to make a few sacrifices: one less dress, no denim jeans (still mourning those), and sadly, no daypack. My packing strategy focused on neutral tones—creams, browns, greens, black—with four pairs of shoes: white sneakers, hiking boots, sandals, ballet flats, plus a pair of slip-ons for around the pool.

Gary packed for 10 days, with gear for both hot and cold weather. He’s the practical one—shocking, I know.

We also had to think about tech and toiletries—my tripod alone weighs 1.35kg! I packed my old GHD instead of the newer (bulkier) hair tools, and contact lenses, which I’ll probably lose at some point. It’s all part of the adventure.

Up Next: Sharing Our Itineraries by Country

I plan to share each leg of the journey in more detail soon. After all, we learned so much from others—what worked for them, what didn’t, where they stayed, what they loved. But everyone’s trip is personal, and what suits one couple might not suit another. Your sense of adventure, budget, and travel style will shape your route.

But if you’re dreaming of your own pause—a proper break from work, routine, and “someday” plans—maybe some of our choices will help spark your own.

Stay tuned.