How I Explore a City

“My ultimate travel suggestions: have fun, take the photos, try the road less traveled, and sit at the bar!”

I love to explore. And after of lot of exploring over the years, I’ve come up with my personal approach to fully experiencing cities—cities that are new to me or my old favourites. I can enjoy a city purely as a visitor or work to see it from a local’s perspective.

First on my list: I find the water. If I’m in a city near water, I will find a way to be on it or in it. I always do a boat cruise. The views are great and you learn a lot about the city. I recently took the Chicago Architecture River Cruise and loved gliding by spectacular views of the Chicago skyline. In London, I always recommend that visitors and locals take time for the river cruise.

If the city has a hop-on/hop-off tourist bus, I grab it. I especially love open-top buses. If I’m showing friends around London, I insist that we go on the London Open Top Bus. It’s easy, you see a lot, and it’s a lot cheaper than Uber.

I like to pester locals for recommendations. I ask my hotel concierge where they go with their friends and family. While sipping a G&T, I ask bartenders and bar patrons for their favourite haunts. Then I eat where the locals eat. I always encourage fellow travelers to ditch the chain restaurants and find the holes-in-the-walls, the independent restaurants that reflect the local culture and cuisine.

Another way to experience local lifestyle: take advantage of locally-hosted experiences offered through services like Explore Withlocals and AirBnb Experiences.

I travel on my own a lot and I don’t bother with restaurant reservations. I can almost always get in, especially since I’m happy to sit at the bar. (Especially at a rooftop or waterfront bar!) It’s my favorite spot. I get to talk to other patrons and can always get great insights on the city from the bartender. (Read about enjoying dining solo.)

But I don’t stress if I can’t get into the restaurant I was shooting for. I walk a block or two and typically find a great restaurant away from the tourists, where locals eat. That’s what my Mum and I did on a recent trip to Florence. Diverting from our plan on where to eat meant finding some of the best Italian food I’ve ever had.

Bruschetta and a variety of Italian foods

Connecting with locals means doing the best you can in the local language. At a bare minimum, I learn “please” and “thank you” in the local language. I find that the effort is appreciated by people I engage with, even if that’s as far as the conversation can go. My go-to resource for translation is Google Translate, for speaking and reading words in local languages.

Like finding the water, I also always work to visit a local market—anything from a weekend farmer’s market in a U.S. city to the vast alleyways of souks in the Middle East. I especially love local markets in India. The array of spices, colours, street food, and smiles is incredible.

Local markets are usually best early in the morning and I’m almost always up at the crack of dawn, wherever I’m exploring. I was recently in Washington D.C. and went to the Lincoln Memorial in the afternoon. It was mobbed with visitors and I couldn’t get near it. I scrapped that plan and went to a museum instead. The next morning, I was back at the Lincoln Memorial at 7am, just as the sun was coming up. It was just a few other people and me to experience the power of that stunning place.

Being willing and able to shift my plans like that is key to how I explore cities. I work to stay flexible. To research and have a plan, but not to over plan. To be OK with changing plans, even at the last minute. With tools like Instagram, TripAdvisor, and web sites for local attractions, it’s easy to find alternative things to see and do near where you are.

And that means walking! Despite my love of fashionable shoes, I almost always have comfy ones on so I put in some serious miles. On a recent trip to New York City, my best friend and I averaged 20 miles a day on foot.

My bottom-line rule when exploring cities: have fun. I don’t let myself get stressed or disappointed in my plans don’t work out. I just make different plans! I call up my favourite travel apps (like TripAdvisor, Timeout, Expedia, Get your Guide, Culture Trip, and Noken) and explore my alternatives.

My ultimate travel suggestions: have fun, take the photos, try the road less traveled, and sit at the bar!

“The world is a book and those who do not travel only read one page.” — St. Augustine

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