Heading off solo around the world - first stop, Manhattan
A Tearful Goodbye on a One‑Way Ticket
After a tearful farewell to my parents at Heathrow, I was soon high above the Atlantic on my way to New York, the city I’d fallen for during a brief stop the year before. It was the first stop on my one‑way ticket to Australia for an open‑ended Working Holiday, via the USA, the Cook Islands and New Zealand.
My First Backpacker Mistake: The Limo
Walking out of Arrivals at JFK, I was greeted by an enormous taxi queue. I’d barely been standing there five minutes when a well‑dressed man approached and asked if I wanted to share a stretch limo to Manhattan with a few others. Forty‑five dollars.
This was the start of my massive backpacking trip. I was on a tight budget. Why on earth would I spend $45 on a limo?
Because I’m an idiot. And that’s exactly what I did.
Luckily it was rush hour and the limo came with free vodka. I took full advantage. Two hours later I stumbled out of the stretch limo, half‑cut, into the hostel reception and was greeted by confused looks from fellow backpackers who had clearly arrived by more sensible means.
A quick mindset shift was required. Flashpacker to backpacker. Otherwise I’d be home penniless within a month.
Hostel Life and the Art of Making Friends
Fortunately, I slipped into hostel life quickly, making friends with a group of Australians and Scots, some of whom I’m still in touch with 20‑plus years later. I’d never experienced anything like it: meeting people from all over the world so easily. My planned few days in New York became two weeks as we explored the city and drank far too much Budweiser from the liquor store around the corner.
The American Breakfast That Broke My Brain
One morning in a local café, I ordered what I thought was a simple “eggs on toast.” The chef offered me seven different ways to cook my eggs.
Seven. I was English. All I knew was “fried.”
Then he asked what shade I wanted my toast. Shade. In England you get whatever comes out of the toaster which anything from burnt black to warm bread. I opted for “medium brown,” trying to sound like I knew what I was doing.
A brief trip to Niagara Falls before travelling the East Coast of USA
A Trip to Niagara and a Painful Lesson
I eventually dragged myself out of the city for a two‑day trip to Niagara Falls, eight hours north by train. I woke early to pack and noticed my locker padlock was fastened the opposite way round to how I usually locked it. I didn’t think much of it as my passport, camera and travel wallet were all still inside.
A few hours into the train ride, rummaging through my bag, I realised my travellers’ cheques were missing. All $2,000 of them. Turning my backpack inside out revealed nothing. Then the padlock moment clicked. Someone had picked it.
The good news: travellers’ cheques were replaceable. The bad news: Amex customer service was useless and it took five days.
Niagara Falls was spectacular. The Canadian side offered far better views than the American side, which despite being tiny still had a few dimly lit “no‑go” streets. I did the obligatory Maid of the Mist boat trip, got soaked through, and loved it.
Reuniting With My Brother in DC
Next stop: Washington DC, where my brother flew out to join me for a couple of weeks travelling down America’s east coast.
We stayed in a hostel in the lively student area of Adams Morgan. At the time I was still new to hostels, but now having stayed in over a hundred, I can confidently say I’ve never stayed in one like this.
The Worst Hostel Room of My Life
The bunk beds were triple‑stacked. And there were three of them. In a room the size of a shoebox.
I got the top bunk, naturally. It was so close to the ceiling I kept whacking my head every time I moved. The ladder was useless meaning the only way up was to step on the other bunk users’ faces like some sort of human staircase. The whole thing wobbled like a game of Jenga. Getting down was a leap of faith, like jumping off a garden shed.
It got worse. When we woke in the morning, two extra travellers had joined the nine of us and were sleeping on the floor. I nearly crushed one of them with my Olympic‑style dismount. Out in the common room, more bodies were scattered across sofas, floors, even the kitchen tiles. It was carnage. Clearly someone either couldn’t say no or was terrible at maths.
Touring DC: The Pentagon, the White House, and a Gun
DC itself was alright. We toured the Pentagon, almost exactly a year before it allegedly got hit by a plane. We visited the White House, initially confused because it looked nothing like it did on TV… until we realised we were standing at the back.
We also toured the FBI building, where a cop ended the visit by firing a live gun at a target while smiling and reminding us, “Remember, guns are not for fun.” Hmmm.
Southbound by Train: Richmond to Savannah
From DC we travelled by Amtrak down the East Coast, stopping in Richmond, Virginia, then passing through the Carolinas before reaching the beautiful, historic, cobbled streets of Savannah, Georgia. Founded in 1773, it was once a British colonial capital and a strategic port in both the American Revolution and the Civil War. Today it’s packed with tourists, students, and dolphin‑spotting trips.
We took a boat out to Tybee Island to see dolphins, but that was about the limit of our adventures outside of drinking frozen cocktails at Wet Willie’s legendary bar.
Traveling the East Coast of USA to Florida
Florida: The Humidity State
And then, onto Florida.
The Sunshine State. Or more accurately: The Humidity State.
It was hot. What felt like 100% humidity, the kind that melts your soul. Our first stop was Fort Lauderdale, where in an attempt to save a few dollars we walked from the station for miles with heavy backpacks in the sweltering heat… only to find the hostel had closed and been converted into a motel. We stayed anyway, too exhausted to care.
Meeting Edward, the “Inventor”
That afternoon we debated whether to meet Edward – a man we’d met on the train earlier. He was in his late 70s, casually dressed, confidently spoken, and claimed he’d invented the photo booth. He chatted to us for half an hour, then gave us his number and invited us to dinner.
So there we were, two inexperienced travellers, sitting in a motel room wondering whether we were about to be murdered by a pensioner or treated to a nice meal.
We put on our best clothes (jeans and a t‑shirt) and were picked up an hour later by Edward and his wife in a brand‑new Jaguar. He took us to a fancy restaurant, treated us to a fantastic meal, and even gave us $20 each for drinks afterwards. He’d just bought a holiday home in town, didn’t know anyone, and enjoyed meeting new people. Lovely.
Years later, I looked him up. Turns out he had invented the photo booth, had been mayor of Utica, had lived a colourful political life… and at the time we met him, had a $54 million sexual harassment lawsuit against him from four male employees.
Maybe he did want to do something with us after all.
Miami: Beautiful People, Brutal Humidity
After a brief stop in the Disney town of Kissimmee, we headed to Florida’s glamorous playground for the rich and beautiful – two things we definitely weren’t: Miami.
“Bouncin’ in the club where the heat is on…” sang Will Smith about SoBe, or South Beach. Bronzed, slim, plastic people lined the beach by day and partied all night. Hundred‑thousand‑dollar cars cruised the strip past Art Deco hotels. Clubs charged extortionate cover fees. Boutiques didn’t bother with price tags.
We popped into a few boutiques occasionally – purely to stand under their freezing air‑con to escape the humidity, before being politely ushered out, clearly not their target demographic in our shorts and sandals.
The Road to Key West
From Miami we took a scenic bus to Key West, Florida’s island outpost connected to the mainland by a chain of impressively engineered bridges. The journey was stunning: crystal‑clear water, palm trees, endless beaches.
Key West was brilliant – slower, calmer, beautiful beaches, great bars, many once frequented by Hemingway, and just a stone’s throw from Cuba. We stayed four days, partied, relaxed, and soaked it all in before heading back to the mainland.
Goodbye Bro, Hello Solo Adventure
For my bro, it was back to work. For me, it was the start of an epic solo adventure to the other side of the world.
Next stop: Hawaii.
