The city of Boston is a treasure. There aren’t enough words to describe how much love I have for it. The first time we travel anywhere, there’s always an expectation. We’re influenced by pop culture, articles, history lessons and stories told by friends and family. Sometimes we set the bar too high, like I did for San Francisco. Other times our expectations are low and we’re blown away. Once in awhile, not very often, our expectations are on par with the actual experience. This is exactly how I felt in Boston. I knew it would be incredible and that I would feel right at home.

As much as I loved Boston, there were a few things I didn’t quite expect on my first visit. Nothing particularly mind blowing but things you might want to prepare yourself for. For example, you might want to add comfortable walking shoes and plenty of cash to your must-bring list.

Brick and cobblestone roads are much harder to navigate than you might expect. I’ve had plenty of experience with brick roads and sidewalks - *ahem* I'm looking at you Paris - but the streets of Boston were a challenge. Cobblestone is a feat all on its own. I don’t know how locals do it in heels. If you’re not confident in your walking abilities, I strongly suggest packing a comfortable and supportive pair of gym shoes.

There are intense hills. This was the biggest surprise to me. Beacon Hill is not just a name of a neighborhood. It’s an actual hill that has angles even San Francisco would be proud of. Navigating the hills plus brick and cobblestones is one heck of a workout challenge. If it’s raining, be extra cautious and avoid piles of leaves. They are slippery and will cause you to fall.

It’s not as large of a city in terms of mileage as you’d expect. Maybe this is because I’m used to walking miles to get from Point A to B in Chicago but you can trek most of Boston on foot. Save your cab money and use their public transportation system if you feel the need to hike longer distances at a time. It’s easy to navigate and much cheaper.

Cambridge is right over the river. For those of us geographically challenged, Cambridge seems like it would be further away from Boston but it’s right across the Charles River. It’s an affordable cab ride or you can use their public transportation system. Cambridge itself is pedestrian-friendly so I recommend walking anywhere you need to once you’re there. It’s the best way to explore any new place and it’s full of photo opps.

A lot of the older businesses are cash-only. I was surprised at how many bakeries, shops and restaurants only took cash. Since I didn’t plan ahead and take cash with me (I had a whole $10), and there were no ATMs or branches for my bank, I was out of luck. Why not use other ATM’s....I’m anti-fees.

The people are pleasant, not surly. I don’t know how the east coast has received such a bad rep when it comes to their attitudes. I’ve only had fantastic experiences along the coastline. Boston has a slight reputation for being not particularly friendly and welcoming. While I didn’t stop every random person on the street to ask for directions, the people I did talk to were helpful and accommodating. No one wanted to start a long conversation with me but that’s something I appreciate.

Now that you’ve been prepped with a few warnings before traveling to Boston for the first time, it’s time to plan your trip. Find out where to get the best donuts, where to get unbeatable bolognese and where to stay, We’ve got tons more content coming up on what to do, where to go and what to see. Stay tuned!

In the meantime, check out my travel playlist on Spotify!