The first time I went to Italy was, I think, when I was about 18 or 19 years old. My friend and I took the train down to Milan from Zug, Switzerland (where his father lives), and we got out of the train station without any idea as to where we were going or where we were going to stay. We were young and brazen and clearly not very prepared. I was probably also wearing Diesel jeans and holding a Sony Ericsson T68 in my hand. Sadly, neither of these things were all that helpful as travel aids.

Today it's impossible to imagine traveling without our smartphones and apps like Google Maps, Google Translate, Airbnb, Uber, and many others. I know that Uber has received its share of criticism over the years, but if you want to fully appreciate what Uber brought to the world, go to a place that you don't know, that is generally unsafe, and where you don't speak the language. It becomes invaluable. (This was Rio de Janeiro for me.) But even without all three of these things, it's an incredibly powerful tool.

In situations where there is zero overlap in languages, I have also used Google Translate to have entire conversations. When push comes to shove, I prefer this approach over trying to impose English (or French) on someone. After all, I am the visitor. I should be the one bending as much as possible. You can also use the app to photograph a restaurant menu and have the entire thing translated in realtime. This to me -- realtime reading -- feels like a powerful use case for when augmented reality arrives.

I also like to use to Google Maps to fastidiously track where I want to go and where I have been. I love logging my travels, and that is much easier to do today compared to the Diesel jean days. I also try and remember to pre-download whatever maps I need so that I'm less reliant on roaming. Here is what Marseille and Sicily look like right now following our trip:

(If any of you are looking for recommendations, CRABE-TORO was our absolute favorite restaurant in Marseille and Càssaro was our favorite place for a drink in Noto, Sicily. We, unfortunately, never tried the food at the latter, but I'm sure it's terrific.)

Technological change has always elicited criticism, negative externalities, and some people wishing that things would just remain as they are. And there is, of course, something liberating about getting off a train in a foreign city and figuring out things as you go. In Milan, we simply walked into various hotels, asked them what their rates were, and then probably got taken advantage of as two young Canadians.

At the end of the day, though, I am a firm believer that the world is a better place because of technological progress. From the Gutenberg printing press to Google Maps, technology empowers us as humans. And I have little doubt that 10 years from now we'll all be traveling with some sort of augmented reality device and romanticizing the good old days of pins on a Google Map.

For the Canadian readers out there, I wish you all a happy Thanksgiving weekend. I am back in Toronto and regularly scheduled programming will now resume on the blog. I hope you enjoyed some of the post diversions over the last 10 days.

Photo taken at La chiave in Catania, Sicily

I have written before about how Lisbon’s kiosks both anchor and beautify the city’s public spaces. I have also written about how Toronto should have something similar — #KioskTO anyone?

Some of you might remember an expanded street food program that the city piloted many years ago. It was a complete and utter failure. In my opinion (and from what I can remember), it was too heavily regulated. The food ended up being far too expensive and, frankly, none of it was very good.

That’s not how this should work. The entire point of things like food trucks and street kiosks is that they are cheaper alternatives to a conventional physical location. You can also more easily place them in locations where demand is being underserved.

The one pictured here is in Catania, Sicily. I carried my beer over from a panini shop down the street and then we ordered three espressos for a total of 2€. I tried to sit on a crate they had lying on the ground but I ended up breaking it. Sorry, guys. So we stood instead. It was all rather civilized.

Let entrepreneurs figure out what to sell and where. It will be a boon for both small business and for our public spaces.

P.S. I tweeted this photo out earlier today and it elicited a good discussion on Twitter. Toronto wants this.

The first time I went to Italy was, I think, when I was about 18 or 19 years old. My friend and I took the train down to Milan from Zug, Switzerland (where his father lives), and we got out of the train station without any idea as to where we were going or where we were going to stay. We were young and brazen and clearly not very prepared. I was probably also wearing Diesel jeans and holding a Sony Ericsson T68 in my hand. Sadly, neither of these things were all that helpful as travel aids.

Today it's impossible to imagine traveling without our smartphones and apps like Google Maps, Google Translate, Airbnb, Uber, and many others. I know that Uber has received its share of criticism over the years, but if you want to fully appreciate what Uber brought to the world, go to a place that you don't know, that is generally unsafe, and where you don't speak the language. It becomes invaluable. (This was Rio de Janeiro for me.) But even without all three of these things, it's an incredibly powerful tool.

In situations where there is zero overlap in languages, I have also used Google Translate to have entire conversations. When push comes to shove, I prefer this approach over trying to impose English (or French) on someone. After all, I am the visitor. I should be the one bending as much as possible. You can also use the app to photograph a restaurant menu and have the entire thing translated in realtime. This to me -- realtime reading -- feels like a powerful use case for when augmented reality arrives.

I also like to use to Google Maps to fastidiously track where I want to go and where I have been. I love logging my travels, and that is much easier to do today compared to the Diesel jean days. I also try and remember to pre-download whatever maps I need so that I'm less reliant on roaming. Here is what Marseille and Sicily look like right now following our trip:

(If any of you are looking for recommendations, CRABE-TORO was our absolute favorite restaurant in Marseille and Càssaro was our favorite place for a drink in Noto, Sicily. We, unfortunately, never tried the food at the latter, but I'm sure it's terrific.)

Technological change has always elicited criticism, negative externalities, and some people wishing that things would just remain as they are. And there is, of course, something liberating about getting off a train in a foreign city and figuring out things as you go. In Milan, we simply walked into various hotels, asked them what their rates were, and then probably got taken advantage of as two young Canadians.

At the end of the day, though, I am a firm believer that the world is a better place because of technological progress. From the Gutenberg printing press to Google Maps, technology empowers us as humans. And I have little doubt that 10 years from now we'll all be traveling with some sort of augmented reality device and romanticizing the good old days of pins on a Google Map.

For the Canadian readers out there, I wish you all a happy Thanksgiving weekend. I am back in Toronto and regularly scheduled programming will now resume on the blog. I hope you enjoyed some of the post diversions over the last 10 days.

Photo taken at La chiave in Catania, Sicily

I have written before about how Lisbon’s kiosks both anchor and beautify the city’s public spaces. I have also written about how Toronto should have something similar — #KioskTO anyone?

Some of you might remember an expanded street food program that the city piloted many years ago. It was a complete and utter failure. In my opinion (and from what I can remember), it was too heavily regulated. The food ended up being far too expensive and, frankly, none of it was very good.

That’s not how this should work. The entire point of things like food trucks and street kiosks is that they are cheaper alternatives to a conventional physical location. You can also more easily place them in locations where demand is being underserved.

The one pictured here is in Catania, Sicily. I carried my beer over from a panini shop down the street and then we ordered three espressos for a total of 2€. I tried to sit on a crate they had lying on the ground but I ended up breaking it. Sorry, guys. So we stood instead. It was all rather civilized.

Let entrepreneurs figure out what to sell and where. It will be a boon for both small business and for our public spaces.

P.S. I tweeted this photo out earlier today and it elicited a good discussion on Twitter. Toronto wants this.