App vs. Friend

US Wealth Napolitano |

By: Alex Weiss, CFP®

It feels like every day someone is telling me about a new app that ‘I have to download.’ It can be anything from ordering a cup of coffee in advance so you don’t have to wait in line or providing a review of a restaurant. Ashley and I recently took a trip to Chicago and as you would imagine, I built out my lists and worksheets to make sure we utilized every minute while we were there. What this trip reiterated to me was the app on my phone can help give a general review, but it does not replace the personal conversation with someone familiar with the area. Especially if they know you personally.

One of the hardest decisions as we headed to Chicago was #1, where do you get deep dish pizza and #2, with only 3 possible dinners, where should we dine out! Let’s tackle the pizza as an example. If you google best deep dish pizza in Chicago, you get 15,800,000 results in less than a second. Now how is a boy from Boston supposed to figure out which place is the best without eating deep dish for 9 meals over a long weekend (I considered that as an option at one point!). Then you go to the food review apps – same issue - it is hard to sort out which one is ‘the best’. Our solution was to ask someone that has similar taste and knows the Chicago scene. For those of you keeping score at home, the winner was Lou Malnati’s – and if you have not had the butter crust pizza, you are missing out!

Chicago is a large city, especially compared to Boston, and it is impossible to do everything over a weekend. But with the guidance of the same friend who helped us figure out the pizza situation – she guided us to the Architecture tour (which we never would found, and it was very enjoyable), museums, Navy Pier, multiple parks, a few roof top bars, and had dinner at our first Michelin star restaurant (which we wouldn’t have even known if we didn’t literally walk into the sign!).

While I am just as guilty as the next person about relying on an app for instant feedback or a review, it was worth taking the extra time to speak with someone that knows the area you are traveling to. With the back and forth we had, we built the best itinerary we could and even though we did a lot, it did not feel like we were running around the entire time. A shout out to NC for the help!

If you are ever traveling to Boston (no matter the distance) and have something specific you are looking to do or eat, always feel welcome to give us a call! Between myself, John, Fletch, Tom, Jenn and the team, I am sure we can recommend something that you would love.

Until next time…