A tour guide can extend horizons for a solo traveller, writes Stephanie Holmes.

After being screamed at by an angry homeless woman within my first 15 minutes of stepping outside my hotel, I wasn't sure I was going to enjoy my time in Portland.

It was raining and the grey skies were mirrored in the grey streets, the Willamette River snaking powerfully through the city like a major artery. It didn't help that it was Halloween, I was jetlagged and I didn't really have any idea where I was going or what I was going to do with myself.

Travelling alone can be a blessing and a curse, sometimes both at the same time. There's a sense of joy in the freedom it affords you — you can go wherever you want, whenever you want, without having to explain or commit to anyone else.

A tea-tasting flight at Smith Teamaker. Photo / Travel Portland
A tea-tasting flight at Smith Teamaker. Photo / Travel Portland

But when you're a stranger in a new town, that freedom can sometimes be overwhelming, often lonely.

You really need to put yourself out there to meet new people — there's no safety net in the same way there is when travelling with a friend or a partner.

A place like Portland — known for its super-cool hipster vibes, world-class food and huge craft beer scene — can be slightly intimidating. Where do you start in this city of approximately 77 breweries and 3744 restaurants? And who will you to talk to while you sample the city's best?

Well, that's where a guided tour becomes your new best friend. You get to find some of the most amazing spots in the city and — best of all — you have an automatic posse of new pals to enjoy it with. Even if you're the only one booked on to the tour, there's always going to be a guide, and they're obliged to talk to you, it's their job.

On my trip there last year, I found three great ways to see and experience Portland, no friends necessary.


Portland is a sprawling city and its 77 breweries are dotted across its 95 official neighbourhoods.

Navigating public transport is no fun when you're on holiday, especially if you're getting merry drinking beer, which also means self-driving isn't an option.

Touring with Cycle Portland. Photo / Travel Portland
Touring with Cycle Portland. Photo / Travel Portland

Enter Brewvana, a tour company that will take you to some of the city's best breweries either on foot, or by mini-bus.

I was on the Pacific Northwest is Best tour, visiting four different breweries and sampling a few different beers at each. The four-hour itinerary is enough to really get you well-oiled and, quite frankly, ready for bed.

Our guide, Benjamin, was the perfect Portland host — he moved to the city for the beer, and now takes great pleasure in showing guests the best on offer.

He drove us around in a 12-seater mini-bus, which had the tour rules printed clearly on the wall — including be respectful of others and yourself and, worryingly: "no puking on the bus".

We visited four of the city's best independent breweries — Culmination, Laurelwood, Ex Novo and Lompoc, spanning a few blocks of the city's Eastside. Although, really, you have no need to know where you are or how it relates to the rest of the city as your guide will get you everywhere you need to go, tell you how long you have at each stop, show you where the toilets are, remind you to pick up all your things when you leave, before dropping you right back where you started as if the whole thing never happened.

The tour is a happy medium between complete craft beer nerdery and beginner basics — our group of four spanned those categories and everyone seemed to leave happy. And probably a little drunk.


I was surprised to learn The Big Foody, a walking tour company, began in Auckland 10 years ago. It was founded by British expat Elle Armon-Jones and the tours are designed to showcase a city through the eyes of a local. She runs six Auckland itineraries, plus one in Canterbury. The idea has proved so successful her friend, Laura Morgan, transported it to Portland and launched The Big Foody PDX.

Laura's not from Portland but she was drawn there thanks to its amazing food and drink and now loves sharing it with visitors. She has excellent industry contacts, so knows the places to go that aren't necessarily easily found by tourists.

We were due to meet for our tour at Smith Tea, a boutique tea-maker and cafe on the central southside. Walking there in the middle of the day, I wondered if I had somehow got lost ... there was nothing but warehouses all around and the area had a rough around the edges, "should I be here alone?" kind of vibe.

But, out of nowhere, Smith Tea appeared, a tranquil space where I sampled four different varieties with pleasant names, like Red Nectar, Meadow and Silent Night.

Across the road, a non-descript doorway lead to Olympia Provisions, one of the best charcuterie restaurants I've experienced. If I'd been on my own, there's no way I would have walked through that random warehouse doorway, too fearful of potentially having taken a wrong turn. But with Laura's guidance, I felt as if I was getting an insider's glimpse at a hidden secret.

Olympia Provisions. Photo / Travel Portland
Olympia Provisions. Photo / Travel Portland

We walked many blocks, sampling some of the best local produce — Jacobsen Salt, hard liquor from New Deal distillery, and heavenly chocolate at Cloudforest.

All the producers had something in common with Laura — none of them was from Portland, but they have grown to love it thanks to its excellent food and drink scene.

And, thanks to my tour with Laura, I started to feel that way too.


One of the best ways to see a new city is by bike. You can get in among its hidden neighbourhoods, away from the well-trodden tourist paths, and discover things it would take hours to find on foot.

If that sounds appealing, meet Cycle Portland, a tour and bike rental company conveniently situated downtown, close to the river and the weekend markets.

Portland is a great city for cycling, with more than 550km of bike paths, and the majority of drivers patient and happy to let cyclists pass.

We cycled an easy 12km over the course of four hours, across some of Portland's famous bridges over to the trendy Central Eastside of the city. Each stop negated the calories we'd just burned on the bike as there was a small feast waiting for us.

Like every New Zealander knows, a day can't start without coffee, so our first stop was Cup & Bar, the cafe combining Trailhead Coffee and Ranger Chocolates. These two companies both have a focus on ethical, sustainable, small-batch production and distribution. Trailhead even delivers its beans to local cafes by bike.

Portland has become synonymous with food carts — this is the city that launched the trend that enables talented chefs to get their start in the industry, without the burden of high leases and overheads. There are now more than 500 carts around the city and competition is fierce.

Sam, our cycle guide, took us to one of his favourites, Cartopia, a pod of food carts in the super-cool foodie neighbourhood of Hawthorne. A giant serving of Portuguese chicken and potatoes meant it was hard to get back on my bike — luckily we took a gentle ride through leafy suburban streets. By the time we made it to Fifty Licks, I had made room for a scoop of their gourmet icecream.

We rode along the Willamette River, heading back to Cycle Portland. Their base was only a street away from where my Portland experience began — the corner where the angry homeless woman screamed obscenities at me.

But this time, the sun was shining and everything looked a lot brighter. All it took was a few new friends to show me the vibrant heart underneath the city's hard surface.

Spirits from New Deal craft distillery, Portland. Photo / Supplied
Spirits from New Deal craft distillery, Portland. Photo / Supplied



United Airlines

flies from Auckland to Portland, via San Francisco. Return Economy Class fares are from $2158.

House of Travel has deals for flights and three-night accommodation in Portland from $1810pp.