Five Strategies for Discovering a New City

Almost daily I get an email asking for travel advice. Some come from regular readers, while others come from those who have stumbled upon my site through Google. Either way, I’m happy to help when I can, though I do with a bit of trepidation. You see, I think travel is like perfume—personal and very difficult to choose for someone else. We all have our own preferences, interests, priorities, and budgets, so what constitutes my ideal trip might be torturous or inconceivable for someone else. However, there are basic strategies for discovering a new city, no matter your taste.

Last week, my father asked me if I would help his neighbors plan their first ever trip to Paris. In their 70s, the neighbors are well traveled, but somehow Paris has eluded them. Taking into consideration their age alone, I thought that my Paris vision would be much different than theirs. Though after a series of questions, I discovered that their laundry list of things to see and do sounded much like mine as a first-time visitor to the City of Light.

Probably the one site that every visitor to Paris wants to experience.

With airfare and hotel secured, we poured over maps and possible itineraries. The more information I threw at them, the wider their eyes got. I could tell they were a bit overwhelmed by it all. The thought of navigating a massive city without speaking a lick of French was a daunting prospect. They’d waited their entire lives for Paris and wanted to make the most of their visit. I could totally relate.

After about two hours, I left the neighbors with some homework: Figure out what you want to leave Paris having seen and experienced—a priority list, if you will. A few days later, I returned and together we came up with a rough itinerary that will be polished as their October departure date draws nearer.

Paris can be overwhelming for a first-time visitor.

Last week, I got an email from a lady in Tennessee who is trying to plan a trip to Ireland for her over-worked oncologist husband. Before that, a woman in Ohio who wants to bring three generations to Texas for a summer vacation also contacted me for advice. By helping others in their trip planning, I was reminded how difficult it can be for the average person to organize a holiday. Even as someone who travels as much as 75% of the time, I sometimes find this to be true. I can only imagine how intimidating it must be for someone who maybe travels once per year.

Like I mentioned earlier, travel is not a one size fits all. However, I find myself offering some of the same advice repeatedly. It’s sort of like the little black dress of travel advice—customizable and can conform to most tastes. Given that I often dole out the same advice, I decided to put it into a post. Thus, here are five strategies that I often employ when traveling to a new city.

Private Guided

If you’re a regular reader of my website, then you know I’m a huge fan of private guided tours. Kensington Tours has organized experiences for me in Budapest, Vienna, Hong Kong, The Philippines, Paris, and Bordeaux. And I’ve explored Florence, Umbria, Rome, Naples, and the Amalfi Coast with Walks of Italy.

 Ilaria led my tours at Pompeii and in Naples.

This is my absolute favorite way to experience not just a new city, but also rediscover one that I’ve visited previously. I would definitely look into this option, especially if you have limited time and don’t want to spend it standing in line and navigating the city. I’d also suggest private guided experiences when visiting historically “heavy” places like Versailles and Pompeii. Without my Walks of Italy guide, I wouldn’t have had a clue as to what I was looking at in Pompeii. A great private guide will make a place come alive and alleviate any stress associated with traveling to a new location. If you have a particular passion such as wine, art, history, or food, then find a guide who specializes in that area. It truly makes a world of difference.

Milos Curik, named one of the world’s best guides by Travel + Leisure, showed me Prague.

Personal attention does come with a price tag to match. In a place like Paris, expect to pay around 250 euros for a half day and 350 euros for a full day. Beyond access to their expertise, additional value comes from the special opportunities afforded to those with private guides, such as not waiting in line and access to areas unavailable to the general public. For instance, by using Walks of Italy, I was able to look inside of a private chapel in the Vatican Museums, escorted by the Swiss Guard.

City Pass

One of the things I always look at when traveling to a new place is a city pass. It can be one of the best values around. Normally this card provides admission or discounts to the most popular tourist attractions, museums, and activities. In larger cities, there are often multiple vendors, thus it’s important to take a look at the benefits and figure out if a city pass is a good fit for your travel plans.

City passes include admission to some of most popular tourist sites, like Versailles.

I’ve used city passes throughout my travels, including Dublin, London, Salzburg, Vienna, and New York. For my January trip to Paris, I received a Paris Pass. Valid for two, four, or six day durations, it includes access to the Louvre, Versailles, Centre Pompidou, the Orsay Museum, and sixty other museums and monuments. Also included is a metro ticket valid for two days of unlimited travel within zones 1-3, which is essentially all of Paris.

Since many of these attractions were places I was going to visit, the Paris Pass was a smart thing for me to have. What I found really extraordinary about the Paris Pass is that it’s actually three individual passes: Paris Museum Pass, Paris Attraction Pass, and Visite Pass. The cool thing is that I didn’t have to activate all the passes at once since all three are separate cards. For instance, I only activated the Paris Museum Pass, which was good for two days. The others are valid for a year, so when I return to Paris in the fall, I can still use the other two passes.

Admission to the Louvre is included with the Paris Pass

Very often, a city pass is a great value if it is actually utilized. I have found tremendous value in some cities and not in others. Though, I’d definitely check it out when planning a urban trip.

Hop On—Hop Off Bus

This may come as a surprise, but I really like a hop on—hop off bus tour. I’ve taken them recently in Dublin, Paris, and Budapest. What’s great about this kind of touring is that it gives an overview of a city, while allowing visitors to get their bearings. An audio guide accompanies the tour, which gives the history of prominent attractions, as well as insight into the culture and information on the city’s most noted people. I call it the Cliff’s Notes tour.

Hop on–hop off buses provide a great overview of a city

Often I’ll buy a 24-hour ticket on my first day. Not only does this give me a lay of the land, but I also discover unknown places that are worth a visit. In addition, this is a terrific way to explore when you’re suffering from jet lag. I actually fell asleep on a bus in Dublin! This was no big deal, as I could just take another loop around.

On a nice day, get an open-top bus for great views

If you’re very limited on time or just interested in the main attractions, this is a great option. It’s easy to figure out—just go to one of the designated stops, pay the driver, and get on. Then just disembark at your desired location. Some of the city passes also include hop on—hop off tours, so be sure to check that out.

Apps and Audio Tours

For the more independent and tech-savvy traveler, smart phone apps offer an unlimited resource when traveling. There truly is an app for everything. Beyond apps that track flights, convert currency, and book hotels, there are some really great options to use for touring.

Mozart’s birth house in Salzburg had it’s own app downloadable on site

On my first visit to the Vatican Museums, I found an amazing interactive guide for my iPhone. With interactive maps, two hours of audio, over 170 photos, and even route planning, I still think this is one of the best apps I’ve used. More recently, I visited Mozart’s birth house. At the entrance, there is a Wi-Fi spot and a QR code to scan. From there, visitors are taken to the iTunes store and the free app that includes an audio tour of the museum. I think it’s super handy and forward thinking to include that Wi-Fi hotspot.

This Vatican Museums app is one of my favorites.

There are tons of other apps that are helpful when visiting a city—they run the gamut. I normally head to the app store before jetting off and search for the city or country name. Then I just comb through the apps to see if anything sounds interesting. When traveling to a foreign country, it’s always a bonus to download an app that can be used offline, since data is expensive and searching for Wi-Fi can be inconvenient.

Another way I like to utilize my iPhone is by downloading audio tours from iTunes. As goofy as I find Rick Steves, he has some great audio tours available. I used three of his tours during my first trip to Rome. They are interesting, easy to use, and educational. I also downloaded an audio tour of Central Park in New York City. Just a quick search on the iTunes store yielded that find. Plus, it came with a downloadable PDF map that was very helpful. Often times these tours are even free. It’s also worth looking at the tourism board’s website for resources. I know Houston offers three different audio tours, and I’m sure many others have something similar.


One of my favorite ways to discover a new city is to just set out on foot and wander around. No plan—no guide. By doing this, I see things that aren’t on the tourist track, but are equally as awesome. I figure I always can find the Roman Forum, but that little restaurant with great people watching and Jewish artichokes might not get discovered if I only follow my set agenda.

View of Prague from the Metronome

I don’t believe there’s a right or wrong way to travel. Instead, it’s about personal preference. Even in planning my own trips, my approach varies based on location and interests. But what doesn’t seem change are these suggested strategies, which can be adapted to fit most any person’s travel style.

Do you have a favorite general travel tip? If so, let me know in the comments.

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  • Tim
    April 18, 2014

    I couldn’t agree more. So difficult to apply the emotions and passion that drive one person to fall in love with a place, onto another person. It really is such a personal preference.

    • Leah Walker
      April 20, 2014

      When I don’t particularly care for a location, I try not to pass that on to others that are planning on going. I don’t want to cloud something that others may love. Hey, to each his own.

  • Sally@Toddlers on Tour
    April 19, 2014

    I love how you said the idea of travel is different for everyone. It is so true.

    Your own ideas of travel also alter as your get older and your circumstances in life change.
    eg. as a child I camped with my parents, as a young adult I drove around Australia, then backpacked around the world. Now in middle age (my god am I that old) with a child I look for relaxation with kids clubs, I know that when my child becomes a teenager then an adult my ideas of travel will evolve again and again.

    • Leah Walker
      April 20, 2014

      You’re exactly right! My idea of travel has changed a bit over the years, and I imagine it will continue to do so. I expect that having kids is a huge adjustment, and still changes as they get older. It’s ever-evolving.

  • Gran Canaria Local
    April 19, 2014

    We totally agree, Leah. You can make some great discoveries stumbling around. Get your head out of the guidebook and see things you might easily miss if following an itinerary.

    • Leah Walker
      April 20, 2014

      I’ve stopped buying guidebooks. They used to be my travel Bible, though now I like to just wing it or use private guides. Both ways I find things I didn’t expect.

  • Raphael Alexander Zoren
    April 19, 2014

    Very good points, it is often that I’m asked to be a travel agent for my friends!

    • Leah Walker
      April 20, 2014

      I hope you’re giving them great advice!

  • scarlet jones
    April 21, 2014

    I totally embrace the ‘just wander’ approach. Many cities also offer free walking tours and if you stay in hostels they are good sources for additional activities and visirs that you msy not have heard of or considered

    • Leah Walker
      April 27, 2014

      I took a free walking tour in Prague, and it was wonderful. Nice suggestion.

  • Craig Zabransky
    April 21, 2014

    love the hop on hop off approach on the first day… totally gives you the lay of the land… but “falling asleep” in Dublin, how many pints did you have?

    stay touring, Craig

    • Leah Walker
      April 27, 2014

      I had been to a certain storehouse prior, but really, I arrived in Dublin at 6:00 am. This was before I was so good at hitting the ground running. 🙂

  • Traveling Ted
    April 21, 2014

    I definitely give the Dion approach the thumbs up. They call me the wanderer Yeah, the wanderer I roam around, around, around. The Miyagi Hop on hop off approach is also a solid tip.

    • Leah Walker
      April 27, 2014

      Yes, Ted. I should have added your hitchhiking approach. 😉

  • Eliza Snow
    April 22, 2014

    I love all of your strategies, and have used each one at different times and locations. But just wandering around on foot is usually my favorite way to explore a place too. I’m more likely to engage in conversation with the local people when I’m not working against a specific timetable or agenda, and that has led to delightful surprises, ranging from being directed to a favorite hidden garden to being spontaneously invited to join in on a family dinner.

    • Leah Walker
      April 27, 2014

      Great point about the interaction with locals. I find that my best times traveling include chatting at a cafe with those that live in the area. They’re a wealth of information.

  • Lance | Trips By Lance
    April 23, 2014

    I love the Paris pass. It’s a thing of beauty. I’ve only done a hop on hop off bus once, although I’ve meant to do it many times. I think we’ll use them more now that we travel with our son more. That one time we used it was in Bath, England. When we arrived at the train station it was pouring rain and I had been sick for the past week. I couldn’t eat and actually lost 15 pounds. So my idea of just walking around Bath was out the window. We booked the hop on hop off at the train station and used it to really take in more of that beautiful city than we would have trying to walk it. Oh, and the picture inside Versailles reminds me of pretty much the same photo we have there. Only this one includes a 5-year-old boy trying to mimic the naked statue he had just seen. It almost became a horrifying parent moment. But even at 5, he did have some modesty in him.

    • Leah Walker
      April 27, 2014

      First off, I’m gonna need that 15 pound weight loss diet.

      Secondly, the hop on-hop off bus is a great alternative during bad weather. I also have used it as an inexpensive alternative to taxis. 🙂

  • Amanda
    April 23, 2014

    I, too, am a big fan of city passes and hop-on-hop off buses, especially if you’re in a big city you’ve never visited before and don’t know where to start.

    • Leah Walker
      April 27, 2014

      It’s a great introduction if you have an extended time or if you just have a short visit. Either way, I think it’s a winner, too.

  • Vid
    April 24, 2014

    Wander Wander Wander 🙂

    Completely agree with the suggestions, especially the last one. And the picture that you got from the Metronome – that spot is one of my favourites to get a panoramic shot of Prague !

    We have never really dared to get on a hop-on hop-off bus till now, but are tempted to 😉

    • Leah Walker
      April 27, 2014

      I know the bus sounds so touristy, but give it a shot one time and see what you think. It’d be a great place for a photo shoot, especially if it’s open top.

  • Sam
    April 26, 2014

    I love this analogy of travel to perfume: spot on! I generally go for just wandering, but I really like the idea of apps and audio tours, but I’ve never actually tried one, so thanks for these recommendations!

    • Leah Walker
      April 27, 2014

      Yes, give the apps and audio tours a shot. Sometimes I like to get lost in my own world when traveling, and this helps me do this.

  • The GypsyNesters
    April 27, 2014

    We prefer the wander method, with research ahead of time. But sometimes a tour is a good idea, especially in crowded attractions where skipping the line can be huge.

    • Leah Walker
      April 27, 2014

      Oh yeah, especially in the summer when lines are around the block.

  • Robert Bruce
    May 1, 2014

    I must concur with several of the others here, I really, really love the wandering method. I think of one of the trips I took with my wife’s family to San Francisco. They have traveled with us before, so they were prepared for our technique. Aside from a few special places, we would start at one end of the city and walk through various neighborhoods, stopping along the way for food, drink, and entertainment.

    We would use a combination of apps like Yelp and our common sense. It is the best way to explore a city, especially one that you haven’t visited before. Thanks for another great post.

  • Leyla
    July 14, 2014

    Yes! the first thing I do when I get to a new city is ride the public bus… not the hop on hop off but the local city buses – where it’s allowed (it’s not everywhere) I ride to the end of the line, and then ride back. The people who get on and off give me a sense of the kind of neighborhood it is, and I can note the bits I liked – or didn’t – and spend the next few days exploring.

    • Leah Walker
      July 31, 2014

      Public bus…that’s a good idea. I hadn’t thought of ever doing that.

  • Monty
    February 16, 2015

    The older I get the slower I travel. It’s not a bad thing. Now I am on country 142 I find myself going back to my favorite places, Then off to new ones. Things are changing in the world so fast I see new things each visit. One month in a city and I start to learn it not just see it. Hope to live in 10 new city’s in the next two years. You inspired me to stay in Paris again.


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