Harris Financial Coaching Blog

There’s something different about landing in Jamaica. The air changes first. Then the pace changes. And before long, you realize nobody is in a hurry except the people who just got off the plane. During our recent stay at Sandals Montego Bay, we wanted to experience more than just the resort. We wanted a mix of relaxation, local culture, excursions, food, and the small moments that make travel memorable.

Sometimes travel is not just about getting there. It is about how you feel while you are getting there. That was the biggest difference for me on our Amtrak trip from Chicago to Memphis and then on to New Orleans. For three people, we paid about $1,700 total, which came out to about $566 per person. For that price, we booked two Amtrak roomettes instead of trying to squeeze everyone into one space. That was not a small expense, so the real question is fair. Was it worth it?

Some trips are planned around transportation, hotels, restaurants, and a few attractions. Then some trips end up giving you more than you expected. Memphis was one stop on our Amtrak City of New Orleans journey from Chicago to New Orleans, but it became one of the most meaningful parts of the trip. We arrived by train, walked through places filled with music and history, and left with a deeper understanding of why Memphis is not a city you should pass through.

Train travel has a way of slowing you down before you even reach the destination. For this trip, we started in Chicago and took Amtrak’s City of New Orleans route to Memphis. This was the first leg of our journey before continuing on to New Orleans two days later. Since there were three of us, we booked two roomettes instead of one bedroom. This ride was a reminder that comfort, cost, space, and expectations all matter when deciding what type of travel experience is worth

A lot of people visit Chicago for the skyline, the food, the shopping, and the big attractions downtown. And yes, those things are worth seeing. But this trip reminded me that Chicago is much more than the postcard version. There is history here. There is culture here. There is leadership here. There is Black legacy here. For my family and me, this was not just a sightseeing trip. It was a chance to experience a side of Chicago that felt deeper, more grounded, and more rea