Which Walking Tour is Best?

Walking tours are a great way to see a city, whether you’re there for a short amount of time or forever. Not everybody loves taking a walking tour - I think it’s too close to the word “tourist” for a lot of people. But how better to get oriented to a city in a relatively short amount of time? But what kind of city tour was my jam - which walking tour would I recommend to my best friend?

Which Walking Tour is for You?

I’ve always been a proponent of looking up free walking tours when you travel. I may not be in grad school anymore, but the grad school budget is still strong. Recently, though, a tour company called Context Travel came across my radar. The thing that caught me? Their hashtag: #deeptravel. They claim to be “(Very) small group tours for the intellectually curious traveler.” Well, I am intellectually curious! I had to give it a try.

I decided to put it to the test in my own city of Philadelphia. But which walking tour would come out on top?

Free Tours by Foot: Philadelphia

As a seven-year resident, I spend most of my time totally avoiding the historic area of Philadelphia. It was time to educate myself. I recruited my sister to check out their “Independence Mall Tour.” The description of the tour online said it was geared towards “entertaining you and revealing hidden secrets, fun trivia, and light hearted anecdotes” about the area. I don’t know about hidden secrets, but it was definitely entertaining.

This was your typical walking tour - tour guide speaks, move on, tour guide speaks, move on.

Context Travel Philadelphia

In the interest of keeping things even, I signed up for Context’s “Colonial City in Context” tour. The stops looked comparable to the free tour with just enough variation to keep me interested. All of Context Travel’s guides (or “docents”) have to have a Masters or PhD to lead. Mine went to the University of Pennsylvania for history, so you know, I had faith he knew what he was talking about and not just reciting a script.

This tour was still tour guide speaks, move on BUT he definitely did a great job of including us in the conversation. He would ask us what we observed before he jumped into an explanation - one of my most favorite teaching styles in the whole wide world. Honestly, just ask my past students.

Which Walking Tour is Better?

Like any good millennial on the job hunt - I broke this down into a pro-con list to see who comes out on top.

Price: Obviously, guys, the Free Tours by Foot is going to win here. It’s free. Even with a pretty nice tip, it still is way cheaper than the $85/person for the Context Travel tour.

Group Size: One of the reasons I think people hate going on walking tours is the feeling of being part of a herd of cattle, snapping away and straining to hear anything interesting the tour guide might have to share. Free Tours by Foot, being free, attracted quite a large crowd - complete with strollers. It definitely had the cattle feel. Context Travel had 5 people, including the guide. Winner!

Time/Duration: Both tours started at 10am. The Free Tours by Foot ended up being about 2.5 hours. Context Travel was 3 and some change by the end of it. Either way, I needed a snack to get through both of them. But with lunch timing, I would say Free Tours by Foot wins. Food tours might be a totally different story, though.

Content: Number of places? Free Tours by Foot wins (only by a handful of sights). Depth of information? Context wins hands down. Both provided me with some fun facts, but I feel like I actually understood Philadelphia a little more after my Context Travel Tour. Plus there were handouts. I love handouts.

Style: This is going to vary hugely by tour guide, I’m sure. For a science lover on a history tour - neither Free Tours by Foot or Context Travel was boring (and with degree-riddled tour guides for Context…this was something I was worried about!). I feel like my Context Travel guide was way better at answering questions that were off the cuff. Free Tours by Foot seemed a little bit watered down.

After-tour Recommendations: I am big on asking for recommendations on things to do after the tour. In my own city, it was more me observing the options they gave to other people. And they seemed about on par with each other.

Variety of Tours: If you’re visiting a city, Free Tours by Foot has some partners that all work together to offer you some great “pay as you wish” options. And they’ve got food tours! Context seems to have a big variety of tours, but the frequency of tours doesn’t appear to be quite as large. This probably just has to do with supply and demand but definitely check into your travel dates and destinations for either tour!

Hamilton Musical References: ZERO. From both tour groups. Are you SERIOUS, you guys? You both failed this category. But don’t worry, I made my own using Snapchat.

In Conclusion…

If you’re looking for a budget-friendly option (read: you’ve spent 95% of your budget on the airplane ticket and accommodations), go for the Free Tours by Foot. You’ll still get an overview of the area you’re in and you can pepper your guide with questions about what to do after the tour. I’d also recommend this if you’re doing multiple cities in a trip. But for Pete’s sake - remember to tip your guide!

If you’re looking for a way to really sink your teeth into why a place is the way it is, I’d go with (appropriately named) Context Travel. Honestly, yes, it is more than I’d want to spend if I were on a budget trip. BUT. I would be completely satisfied with skipping any museum and going on a tour instead - so if you balance out museum admission with the tour cost it could be more comparable than you think.

Let’s Chat!

  • What’s your opinion on walking tours? After this breakdown, which walking tour do you think you’d choose?

I was hosted by Context Travel on this specific tour, but all opinions are my own - I wouldn't tell you I think something is awesome just for a free tour! Some of these links are also affiliate links - no different for your cost of booking, though!