Do's and Don'ts of The Cross Country Drive.

On Saturday May 20th I left the small town of Highland City in Utah County, Utah to drive across the country to Boston. Not exactly coast to coast, but still a long drive. I broke up the trip so that I only had to drive about 7 hours or less per day. I stopped in Cheyenne, Omaha, Chicago, Pittsburgh, Philadelphia, New York, and finally arrived in Boston.

A couple things I wished I would have done:

Fly to Omaha, rent a car there and then drive to the other cities. Then you aren't technically driving across country, but thats alright because Cheyenne is pretty forgettable.

Book your hotels in advance. I know some people tell you don't book them until the night of. And that is nice because you are more flexible. But then you have to book hotels when you get to a new city. I would rather relax in the hotel or go see something than scour the web for cheap deals.

Just pay... You are gong to pay for parking, Ubers, cabs, food, etc. Know you are going to have to pay more than you expected. If you plan well I guess you can know your budget down to a cent. I went with no plans and tried to save money at the beginning. By the end I would rather pay for parking than be far away from things.

Here is list of the cities and why I liked, loved, or hated them. I'll include hotel recommendations or places to steer clear of.

Cheyenne--Not a huge fan. Not very a very beautiful drive and not a very beautiful city. There was a cool restaurant that had self serving beer taps and good sliders called Accomplice Beer Company. I stayed at the Historic Plains Hotel which I do not recommend. I didn't sleep at all because I could hear people yelling outside and the train going by. Selfie with one of the huge boots in Cheyenne... If a huge boot is the only attraction, might want to keep driving.

Omaha--I loved this small city. It was clean and had beautiful little structures built around the river on almost every block. I walked around the Heartland Park of America and then went to the Old Town to eat. It looked like there were lots of young people out and about. If you are renting a car I would recommend skipping Cheyenne and just flying into Omaha to rent a car and then drive the rest of the way. I would also recommend the New Victorian Inn and Suite. The hotel is 16 minutes from downtown, but very clean and comfortable.

 Chicago--I hear Chicago is so great....But I didn't really enjoy it too much. To be fair it was rainy and I didn't pick the greatest hotel. The city is so big and spread out that there is no way to get a hotel close to everything. I didn't want to take an hour on public transit so I drove downtown (which only took 20 minutes. The problem was it was about 45 bucks just to park for an hour and a half. Super expensive. Maybe I'm just not a Chicago guy, after all I'm thin crust over deep dish pizza.

Pittsburgh--I drove past Wrigley field because I didn't get to see it at night. I was kind of disappointed. I will have to go back and walk around, maybe catch a game. I drove down through Illinois, over across Indiana and Ohio. I took the route with no tolls.. stupid move. I didn't take into account that driving and extra hour or two will just cost me more gas. So I would say spend the money on the toll routs. The drive was pretty boring. I was wishing I would have just stopped in Indianapolis or another city along the way. Once you get past West Virginia and into Pennsylvania, the drive turns into gorgeous green hills and old town nestled in them.

I stayed at the Hampton Inn Pittsburgh/Greentree. It is another clean hotel that I would recommend. They even have a free shuttle that takes you downtown. Pittsburgh is a beautiful city. Lots of young and old people out and a bout to go to bars to watch the hockey game. I will definitely be going back to Pittsburgh. Try and get a sandwich with fries in them. There is also a monastery turned into a bar. I met someone at a bar who was really nice but just wanted to talk politics. I can think of better conversations to be had at a bar.




Philadelphia--Not wanting to make the mistake of staying far away from downtown, I just threw down the extra cash and stayed at Club Quarters hotel. This was a more upscale hotel than I would usually stay. They even had free water bottles with filtered water by each elevator. Philadelphia is a  nice city. It was very busy with all types of people. I saw a lot of people walking around in suits. I met a really nice guy at a bar who said most people in Philly are "dicks." I didn't notice. He took me to another bar and ended up getting in an argument about something with someone else. Definitely go to the Reading Terminal Market and get one of these little donuts. Apple pie filled. Toe curling.

New York--The Big apple just towers over you. The drive was rather quick. Traffic wasn't as bad as expected. I stayed at a Hampton in Times Square--again just wanted to pony up the money and stay close. In Philly I paid about 35 bucks for 24 hours of parking. In New York I paid 90 dollars for 48 hours. You could rent cars and just drop them off in each city to avoid parking fees. I enjoyed staying in Times Square. But New York is like Chicago in that it is so spread out. So you will have to take an uber or subway to get to some destinations. There are millions of restaurants and cool things to see. I really liked The Met (if you are into art) and other restaurants and places to grab a drink. Just do a yelp search to see what is near you. I'd also recommend a show, obviously. Nothing beats the pageantry of seeing a show on Broadway. I chose to go see School of Rock. I got a ticket for 39 bucks, but it was partial view. The partial view didn't bother me because the only things I missed were in the very back or one corner of the stage. The show rocked. I got chills at least five times.

Boston-After New York I finally made the drive to Boston. I was exhausted. I feel like I hadn't stopped in a week. I was either driving, walking around a city, or looking at hotels for the next city. I got a little place in the Back Bay to stay for the month. I love how the Back Bay is next to a bigger city but still has a quiet, smaller town feel.