A 2.5‑Month Journey Across a Continent, a Bucket List, and an Escape From Winter — Featuring Epic Landscapes, Curious Animals, and a Travel Group That Shrunk by the Week

If you ever want to test your sanity, your marriage, and your tolerance for WhatsApp group chats, try planning a 2.5‑month South America trip for a rotating cast of 16 adults. I did. Miraculously, everyone survived, everyone enjoyed it, and everyone told me I did a great job — which obviously means they were either being polite or I accidentally became competent. I’m still processing both possibilities.

This trip had everything: dramatic landscapes, rare wildlife encounters, good wine, a surprisingly lovable country or two, and a slow, Agatha‑Christie‑style disappearance of our travel companions until — yes — then there were none. Galapagos was the official excuse. The real reason? To escape the Canadian winter before it escaped us. Please keep that confidential; I don’t want to be flagged as a snowbird.

How It All Began (a.k.a. My Descent Into Planning Madness of a Galapagos & Other South America Adventure)

Fifteen months before departure, I began researching the Galapagos Islands — a bucket‑list destination that had been sitting there so long it practically became a fossil. These volcanic islands, populated by creatures that look like they were designed by a committee of biologists, demanded a visit.

We’re not luxury‑cruise people. We prefer expedition cruises, where suffering is included at no extra charge. Wake up at dawn. Jump into a zodiac. Hike, snorkel, sweat. Lunch. More hiking. More sweating. Bliss.

And because I apparently enjoy stress, I found a small ship and recruited 14 other willing masochists for an 8‑day/7‑night Galapagos expedition. Yes, I organized it. Yes, it was a lot of work. Yes, everyone said it was fantastic. No, I still don’t know how that happened.

The Original 16: The Start of Our Long South America Trip

Hockey has the Original Six; we had the Original six…teen — older age, fewer fistfights. The Galapagos cruise was only the beginning. Obviously, eight days weren’t enough for us, so we needed to “fill” another 11–12 weeks to reach the scientifically determined perfect trip length of three months. We almost succeeded. Almost

Nursing Time on a Galapagos Beach

Ecuador: The Warm‑Up Act

Since Galapagos belongs to Ecuador, the first leg was a no-brainer.

Five of the 14 Galapagos companions joined us for an 11‑day mainland adventure: rainforest hikes north of Quito, climbing Andean volcanoes, and wandering the beautiful colonial cities of Quito and Cuenca. I volunteered to organize everything — because apparently, I enjoy spreadsheets more than peace — and it turned out spectacularly. People even thanked me. I’m still suspicious.

…and then there were 14… (Rapa Nui & Santiago, Chile)

After Galapagos, twelve of the original group followed us to Rapa Nui (Easter Island). The moai encounter was far more emotional than expected — somewhere between Angkor Wat and the Sistine Chapel, but with fewer crowds and more giant stone heads silently judging you.

Moai in Rapa Nui. They stair at you and you feel they judge every step you make.

We returned to Chile, and all 14 of us explored Santiago. Six members decided they had “more important plans,” which I assume means laundry, Netflix, or simply “we’re checking out before he schedules another volcano.” At this point I also realized I did all this planning — and herding fully grown adults — for free, which in hindsight feels like a questionable business model.

Neptune Terrace at Cerro Santa Lucía — Santiago’s most dramatic staircase to nowhere in particular.

…and then there were 8… (Valparaíso, Wine Country & Atacama Desert)

Each couple rented a car and drove to Valparaíso — a city so colorful and artistic that you almost forget how rugged and dirty it is. Almost.

Street art mural on a step street in Valparaiso

Naturally, we couldn’t be in Chile without visiting wineries. Contrary to what many people think (including myself till I got there) Chilean wine is very good, sometimes excellent, and always cheaper than what we get in North America. Especially in Canada, where wine prices are set by people who clearly hate joy.

After a week of wining, dining, and pretending we understood tannins, we flew to the Atacama Desert. We’d seen the Bolivian side before, but the Chilean version is a whole new level of hot, dusty, and spectacular.

The driest place on Earth, but you can still find 2 lakes in the Chilean Atacama Desert. This one is Laguna Miscanti.

…and then there were 6… (Patagonia & Tierra del Fuego)

After 3.5 days of criss‑crossing the driest place on Earth, one couple decided that five weeks of travel was enough. They headed home. We flew to Punta Arenas — the southernmost city in Chile — rented cars, and drove to Puerto Natales, gateway to Torres del Paine National Park.

To me, Mount Fitz Roy was always the most beautiful mountain I’ve ever seen. After Torres del Paine… let’s call it a tie. A very dramatic, photogenic tie.

We hiked for two full days, returned to Punta Arenas, and boarded another expedition cruise — this time through the fjords of Tierra del Fuego. Stunning doesn’t even begin to cover it. I haven’t seen Norway’s fjords, but if they’re better than this, I’ll eat my hiking boots. As a bonus, we even landed at Cape Horn — a rare treat, since the weather usually says “absolutely not.”

The Pía Glacier in Tierra del Fuego — because apparently the Andes needed one more show‑off

…and then there were 2… (Ushuaia & Uruguay)

The cruise ended in Ushuaia, the southernmost city in the world (this time in Argentina). The remaining two couples surrendered and flew home.

We, however, needed rest after six weeks of hiking, cruising, snorkeling, driving, and general overachievement. So we flew to Montevideo and spent a month eating the best beef on Earth, drinking Uruguayan tannat and albariño, and making friends with locals and fellow wanderers.

Palacio Salvo — because every city deserves a diva.

…and then there were none… (Buenos Aires & Home)

Teatro Colón in Buenos Aires: where the acoustics are perfect and the architecture is showing off.

After a month in Uruguay, we took the ferry to Buenos Aires, inhaled the big‑city air (pollution included), and after three days boarded the flight back to Toronto. Our kids were waiting for us. Who needs more than that?

What a trip. Probably the best I’ve ever planned — and yes, I’m saying that out loud. It wasn’t always easy managing a group that occasionally offered more “helpful suggestions” and “gentle nudges” than strictly necessary, but it was great fun. People liked it so much I’m starting to worry I’ll be asked to plan someone’s wedding next. And that final month in Uruguay, just the two of us, made everything feel perfect. The unpleasant moments? Forgotten. The great ones? Still glowing.