New York – Boston | Road Trip

New York – Boston | Road Trip

New York – Boston | Itinerary

Day One

  • Time square
  • Mugging
  • Pizza

 Day Two

  • Empire State Building
  • Rockefeller Plaza
  • Natural History Museum
  • Bagels

Day Three

  • Freedom Trail
  • Quincy Market
  • Salem


DAY ONE / Time Square

This is without a doubt a vibrant and intimidating city that feels like no other city in the world. The sheer size of it is awe inspiring but the number of people is stunning.

Driving in New York

Don’t. We drove into the city and were staying near Madison Square Garden and if you can avoid it don’t drive in New York.No one respects walking lights or rules and everyone is fighting for every inch of road. If you live there you know the unspoken rules of driving but as a visitor it will seem insane. The horn is used for everything from move to I’m coming through and the streets are seldom absent of one.



When in New York you have to walk everywhere and I was taken back by the city that I forgot to worry about personal safety. A mugger was actually scouting and had his eye on me and Lucy when I noticed him at a red light. He might have thought Lucy was by herself as it did seem like he was about to mug her before seeing me. Instead he calmly but aggressively got in this tourist guy’s face in front of us with his hand in his pocket. The guy’s face looked angry and serious and the tourist started reaching for his wallet. I was shocked this was happening right in front of us surrounded by so many people. I would have expected something like this to happen in an alley or where there wouldn’t be so many people. It happened so quickly as well, there were no police in sight, and the guy disappeared quickly.

That soured me and Lucy on the city  a bit but that is part of living in such a big city like New York. As a reminder keep moving and stick with the crowd when possible to improve your chances of remaining safe.

Time Square

So many lights and so much to see. This is a place just to soak in the environment. There isn’t much to do here but it is worth experiencing being in that area with all those lights and people.

New York Pizza

Having just arrived in New York we had pizza for dinner near MSG at NY PIZZA SUPREMA. The great thing about pizza in the city is the selection and speed. Lucy was the winner with her selection of a simple garlic cheese slice. I tried a couple of different toppings and what I learned was keep it simple: cheese or pepperoni are the best and anything more will just complicate the flavor and take away from the feast cheeses.


Here are some other spots we tried and they are all good but no two spots were the same.

NY PIZZA SUPREMA – Probably the best overall

Little Italy Pizza – Crunchiest crust

Freddie and Pepper’s -Hole in the wall for locals and good pizza

DAY TWO / Empire State Building

Empire State Building in Day

One of the craziest things that happens to you in New York is you lose scale perspective. Because all the buildings are tall no one building looks daunting. We visited the empire State building during the day and night because it has the tallest observation deck. To be specific it has two observation decks: one on the 86th floor and one on the 102nd floor but in our opinion the 86th floor is better and you have to pay extra for the 102nd floor view.

You get sweeping 360 degree views of the city and again you lose scale of everything but looking at all the cars and people below will help remind you of the immensity of the city. From here you can see the statue of liberty, the freedom tower, Central Park, Washington Arch,Time Square, the Chrysler Building, and many more landmarks. Regardless of the season bring a coat as it gets windy and cold at the top.

Empire State Building at Night

As breathtaking as the city is during the day the city never sleeps so it really becomes a festival of lights at night. Time Square by itself seems to light up the entire area but to look at a city with endless lights in all directions is astonishing. Makes you wonder how all this is capable of existing let alone how it got this way.

Rockefeller Plaza

The iconic plaza was starting to be decorated for Christmas during our visit and the plaza was the most pleasant and peaceful area in the whole city. The plaza houses a seasonal ice rink and it is very calming to watch or take part in the ice skating. To my surprise there is a mall underneath Rockefeller Plaza with a view of the ice rink and a great place to grab a snack and coffee.

Near Rockefeller Plaza you will you find yourself near Radio City Music Hall and a architecturally grand catholic church that is open to visitors.

Natural History Museum

Plan to spend a day here if you want to see it all as the place is immense. Our favorite exhibits were the Dinosaurs but we also spent a lot of time in the cultural exhibits. The only exhibits that I did not care for where all the animals as you can go to a zoo and see most of them actually still alive.


You have to try the bagels. It’s all that I heard before my trip and they were right. We tried the bagels at this neighboring bagel shop called Best Bagels and Coffee. We had various bagels:

  • Garlic bagel with eggs and bacon
  • Sesame seed with scallions cream cheese
  • Cinnamon Raisin with regular cream cheese
  • Garlic bagel with tuna salad

They were all amazing and the bagels are different. They are large and thick but soft with just the right amount of crunch when toasted.


DAY THREE / Boston

More than New York we found this city to be pleasant, welcoming and filled with so many historic sites to visit. We chose to walk th

e Freedom Trail which is about a 2 mile trail that takes you through the northern end of Boston and along the rich history of the colonial city. The city of Boston was nice enough to highlight the trail through bricks or markings on the ground so you never get lost.

Boston is exactly what you would expect from a city with great American history: amazing architecture with great exhibits and an ambiance fitting it’s history.

Freedom Trail

USS Constitution

The oldest commissioned warship in the world which means when you board the ship you are on an active warship of the US Navy.

Bunker Hill and Charlestown

The town is just amazing. We even dropped in and had a delicious bowl of clam chowder at a tavern frequented by revolutionary figures in it’s day, Warren Tavern. Preserved throughout the years this is a great way to connect to the past while enjoying a delicious meal. Nearby is the start or the freedom trail at the site of a bloody battle during the start of the revolutionary war, bunker hill.

What a beautiful field and monument for such a bloody event. We climbed the tower and you will want to as well. The whole thing trek takes about 300 steps up a spiral staircase. You reward is a 360 degree limited view of the city and bragging rights.


So many and from so long ago. There are so many graveyards along the trail but they all amount to a chance to see headstones over 250 years old and be able to learn about how people were remembered or honored in the past.

Old North Church and Paul Revere’s Home

Centered in one of the more beautiful areas of Boston the CHURCH signals one of of the most important events in American history. One by land or two by sea. This is the historic spot where Paul Revere placed the lanterns to alert the militia of the approach of the British army.

You even have the chance to tour were Paul Revere lived.  

You can just walk the streets and smell the good food in this area. Drop in on any restaurant and you won’t be disappointed.

We dropped in and were not disappointed by:

  • Mike’s Pastries
  • Pauli’s  

Boston Common’s and Boston Public Garden 

The park  is vast and a pleasant walk filled with several monuments. Bring a lunch and have a picnic or skate around the seasonal ice rink.


A personal favorite for me as a fan of the show. If you are a fan of the show this is a must do I don’t think most people there were fans of the show and the bar isn’t exactly the same but the exterior is exactly as it was during the filming of the show. I was fortunate enough to have a beer in Norm’s seat and got to tour the bar that inspired the show.

Quincy Market

A giant food court filled with decent food but not the best the city has to offer only because the city has so many great other areas filled with amazing food. The ambiance of the place is great and nowhere will you find such a variety of food.


More of a tourist town than I would have expected. I expected a small rural community and what I got was museums and gift shops so that was shocking. We visited the oldest surviving building in Salem and home to one of the Judges during the Salem Witch trials. The trials saw innocent people being executed over Witch hysteria. One of the saddest/angriest things you find out while visiting the house is that the trials didn’t end until the Governor’s wife was accused, as always who cares until it affects you.


Walking through the house is erie and seeing how they lived is astonishing. The house itself is a great experience as you don’t get to walk around a house from the 1600’s very often, let alone the home of someone that sentenced so many innocent people to death without any consequences.

Leave a Reply

Your email address will not be published. Required fields are marked *