East Coast Vacation: DC, Philly, NY, New Haven, and Boston.

View of Manhattan from the Staten Island ferry.

I recently took my family to the east coast for vacation. This post shares not just the fun of traveling, but also the planning, logistics, and costs of the trip. My goal is to inspire you to travel with the understanding that it doesn’t cost a fortune to explore and have a good time.


On June 1, I asked my parents if they would like to go on vacation. They said yes. Three hours later, I booked three one-way flights from LAX–>Baltimore and from Boston–>LAX.

That same night, my mom suggested I invite my sister Cindy. I called. She said yes. I bought a fourth set of flights for her. Family trip official!

Neither my mom nor sister have ever been to the east coast. My dad and I agreed that this trip was ultimately for my mom and sister’s enjoyment. He helped me plan the itinerary:

From June 15-20, we were to visit Washington DC, Philadelphia, New York, New Haven, and Boston.

  • Washington DC: one whole day along the National Mall
  • Philadelphia: one evening exploring the city center
  • New York: two full days exploring Manhattan
  • New Haven: half day touring Yale University
  • Boston: one day touring Cambridge and the Freedom Trail


My travels in recent years have affirmed that I am indeed an impatient, Type A travel snob who’s anxious about every little thing. Therefore I took care of all the travel details.

My family’s travel style is consistent across the board, which made logistics easy. Our goal is to maximize time exploring and minimize time eating food. And the purpose of lodging is to sleep after spending all day outside — no need for fancy hotels.

Flights were booked via United, which was the cheapest option I found after browsing Skiplagged, Google Flights, Southwest, and Expedia. Flights were so cheap that it wasn’t worth booking with points. It only cost $313.40 round trip per person.

Car rental was a Dodge Grand Caravan through Chase Ultimate Rewards. Pick-up at Baltimore and drop-off at Boston. Prices were competitive across all sites, but I used some points to save money. $666.38 became only $247.78 + 33,488 points.

Lodging was five nights in four cities for a total of $469.57. I was able to effortlessly find and secure Airbnb bookings that fit our criteria of:

  • Shower + toiletries
  • Wi-Fi
  • Fridge for perishable goods
  • Enough places to sleep whether it be beds, couches, and/or air mattresses
  • Parking for rental car
  • Safe neighborhood

Food was tricky. When traveling, the Cheng family treats food as nothing more than sustenance. Why spend money and lose time eating at a restaurant when you can bring food in your baggage? Each of our luggage was jam packed with both ready-to-eat and raw foodstuffs, causing (first world) problems at LAX.

Luggage was difficult getting to the east coast, and comically easy (explained later) on the return trip. Our bags were inspected due to all the food items that raised alarm. My Type A personality caused my Type O blood to boil watching TSA take their sweet time rummaging through our belongings. But alas, we were clear for takeoff!

Note: a full accounting of trip expenses is available at the very end of this post.

Washington DC

We landed at 5:41am in Baltimore. None of us got a wink of sleep. We drove to Starbucks and used up some gift cards to load up on lots of caffeine and food. During that time, I registered with SpotHero (highly recommended) and reserved an all-day valet parking spot inside Washington DC for only $19.00.

We arrived in DC at 9am and began our day-long walking tour.

In total we walked 7-8 miles.

The White House was blocked off, but we could still see it from afar.

We walked by Eisenhower Executive Office Building (my favorite building), then to the Washington Monument.

We walked around the WWII Memorial, then to the Reflecting Pool and the Lincoln Memorial. This was where Forrest ran across to hug Jenn-aye.

We walked by the Korean War Memorial. Then to the most boring part of the day because I’m not cultured like every other adult out there… museums. We visited three. I took two fabulous power naps inside the viewing rooms.

Real talk though, I learned a lot about James Smithson. I had no idea he was the patron of the Smithsonian buildings; that the cause of his donation was out of extreme chance; that he was a Frenchman who never even visited the United States. Mighty interesting stuff.

After looking at lots of paintings in many museums and failing to reach an existential crisis, it was time for dinner. We walked to Reren Lamen & Bar to meet up with an old college friend whom I hadn’t seen in five years. Behold, Jonathan Wang!

We last saw each other in DC!

‘Twas the end of the day. Our Airbnb was a studio inside an apartment complex called The Graham. My sister and mom shared a full size bed; my dad the couch; and myself on an air mattress that was fully deflated by morning.

View from the studio.


The drive to Philadelphia was long. We took a spontaneous detour to Gunpowder Falls State Park after seeing the name across the freeway sign. We ate lunch next to a beautiful river.

A little toad stood by us the entire time, hoping to grab leftovers.

Due to the detour, we arrived in Philadelphia late in the afternoon. We scrapped plans to tour the United States Mint and UPenn.

We began our adventure at Elfreth’s Alley, our nation’s oldest residential street with homes built between 1728 and 1836. Yes I Wikipedia’d that.

Real people live here! There were signs that reminded us to keep our noise levels down.

We then tried to walk into Franklin Square, but there was a Chinese festival that had ended. They weren’t letting anyone inside, so the next stop was Liberty Bell!

Looks like the replica at Knott’s Berry Farm, but with a 30-minute wait to see it. Place was jam packed.

And of course, Independence Hall.

Since I was the “tour guide,” my family kept asking me what various buildings were. Google Maps became my best friend and helped me explain that we were looking at the Second Bank of the United States, the Carpenter’s Historic Hall, the First Bank of the United States, the Museum of the American Revolution.

The First Bank of the United States. The kid and the cart ruined what would have been a perfect shot.

On our way back to the parking garage, a signpost “Best cheese steaks in Old Town!” caught my attention. We walked into Fezziwig’s Kettle Korn and ordered some for the family. It tasted pretty good, and I have no basis for comparison on other cheese steaks in town.

Our Airbnb in Philadelphia comprised of two queen beds and a couch in a large room inside a four-story house. My family took the beds while I slept on the couch.

New York

My favorite city of the trip. We arrived at Staten Island at 11am and took the St. George Ferry into Battery Park. We spent the day in Lower Manhattan and Midtown.

Orange is public transportation. Red is walking.

The Ferry runs every 20-30 minutes, 24 hours a day, 365 days a year. It’s completely free. I thought that was so cool and convenient.

On the way there, we enjoyed looking at Governors Island and Manhattan on starboard side. Little did I know that port side was where the majority of folks were looking at Lady Liberty.

Manhattan is completely visible from Staten Island. I was so pumped.

The ferry takes about 20 minutes each way. We arrived, then began walking through the Wall Street area to the Brooklyn Bridge.

Brooklyn Bridge from the ferry.

Brooklyn Bridge in the flesh. It reminded me of Grand Theft Auto IV.

Afterwards, we walked to The Oculus and the 9/11 Memorial.

We spent quite a lot of time there, then took the subway for the first time. Was pretty confusing at first, but turns out it’s very convenient. Things I learned:

  • You swipe a paper ticket through the machine and walk through the revolving door.
  • You can swipe multiple times. Each time it deducts the same amount.
  • The fare is a flat fee of $2.XX. You can go anywhere in the entire subway system on that flat fee.
  • Your ticket gets some free credit if you refill at greater amounts.
  • The subway runs 24/7/365 and is one of the biggest transit systems in the world. By far the biggest in the US.

We got to Chelsea Market, walked through it, and then along The High Line.

Chelsea Market is a big warehouse with foods and shops to browse through.

The High Line is a long decommissioned railway that’s been transformed into a walking park.

For dinner, we ate four small cheeseburgers costing $46.82 in Chelsea Market. I was annoyed at the cost; the Cheng family does not like spending premium numbers on basic foods.

Time to go back to our Airbnb on Staten Island. We enjoyed the Statue of Liberty sunset view.

Our Airbnb was an entire 2 bed 2 bath apartment with a big living room. My family took the rooms, and I took the couch. It was supposed to cost $201.19 for two nights, but we only paid $161.19. I invited my sister to join Airbnb, and she received $40 off her first booking.

I enjoyed our second day in New York equally much. We started in the Grand Central Terminal, walked by the Empire State Building, and then to Times Square.

Looks exactly like what you see in all those movies and YouTube social experiments.

For lunch, we ate The Halal Guys per my girlfriend’s recommendation. Apparently the street food is really famous.

Chicken and beef with rice. The beef was too salty, but the chicken is to die for. We committed a grave sin by throwing out a lot of food — the portions were way too generous.

After lunch, we spent the rest of the afternoon walking around Central Park. I took a quick detour to The Plaza Hotel due to having Home Alone 2 engraved in my childhood memories.

My sister grabbed a map and we followed her lead. Beautiful as the park is, the naming conventions of all the sectors were incredibly bland. “The Pond… The Lake… The Playground…” Come on you can be more creative than that.

It’s incredibly impressive to be immersed in nature, then look up and see we are in the middle of a megalopolis.

We didn’t have any time to visit The Met. That’s because we met up with an old time high school friend, Jackie Napalan!

The last time I saw Jackie was in Summer 2012, when we both studied abroad in Beijing. It’s been six years!

We ate dinner at Patsy’s Pizzeria, then made our way back home. Two days was too short in New York. I plan to return and spend more time exploring.

New Haven

The next day, we started a long drive to New Haven. We drove along the magnificent East River that made me wish I didn’t have to focus on driving. Family stared in awe as well, so nobody took any pictures. Damnit, I miss its beauty.

Along the way, we stopped at a gas station just off the highway in Connecticut. Like it’s literally a pit stop off the shoulder. These cute little stops appeared once every few miles, reminding me that Connecticut has the 3rd highest GDP per capita in the country.

We arrived in New Haven shortly after noon. Our sole purpose was to tour Yale University. Boy was it pretty!

Here’s a pretty building whose purpose I do not know. Guessing it was dorms.

Here’s the building I was convinced was the library. We walked in and discovered it was the gym.

Here’s the library that looks nothing like what you can Google. Perhaps I suck at taking photos.


We originally wanted to go to Newport, RI to see the tycoon mansions along the coast. Unfortunately we were behind schedule and had to drive straight to Boston.

We arrived in the small town of Somerville adjacent to Cambridge, parked at our Airbnb, and walked to the restaurant Waypoint. There we met Susan Park and Adil Islam.

Dinner was fantastic and comprised of oysters, fries, fancy appetizers and shrimp, an entire grilled fish, and seafood pizza.

After dinner, Adil (a Harvard alum) gave us a magnificent tour of the campus, including the square where Zuckerberg ran across campus to become an accidental billionaire — I learned that from The Social Network.

Susan dropped my parents off at the Airbnb. Cindy and I then spent several hours hanging out at Susan and Adil’s apartment. We played with their lovely dog, drank some dank oolong tea, caught up, and took a selfie.

Accidentally matching.

We called it at midnight, walked back to the Airbnb, and slept soundly.

The next day was spent touring MIT and walking the Freedom Trail. We walked across the Charles River through Massachusetts Ave. and met up with my dear roommate from college, Sameer Abraham!

Sameer is doing his Ph.D in Physics at MIT and gave us a gracious school tour.

The largest lecture hall on campus.

Fun fact: all the buildings on campus are just labeled as numbers. They’re also randomly assigned, so one could walk from Building 4 to Building 11. One also does not really know when they walk into another building, except when looking at it from a map. Nerds man, I tell ya.

MIT Library from the outside. Another fun fact: the mound of dirt behind us is from the graduation ceremony took place just a couple weeks earlier. I felt like a MIT grad, except for the smart part.

After saying our goodbyes to Sameer, we took an Uber to Bunker Hill. We started at the end of the Freedom Trail and backtracked to the beginning in Boston Common.

The British are coming! The British are coming! Unfortunately no good pictures to show. I was playing tour guide while my family took massive amounts of pictures.

Here’s us eating four burgers that cost $30.99, still expensive but at least 25% cheaper than New York.

We walked through Back Bay to the parking garage. I rushed the family due to the risk of missing our flight. A certain sister *ahem* spent a little too much time shopping for souvenirs for her friends and husband’s family.

Driving to the airport was an absolute nightmare. It was close to 3:00pm, and the traffic in Boston was abysmal. We arrived at the gate 10 minutes before boarding time, and my Type A anxiety finally came to an end as we had safely concluded our wonderful family trip.

Didn’t I mention earlier that luggage on the way back was comically easy? To elaborate, the Cheng family threw away their clothing each night. These were very old clothes collected over the years that were to be worn one last time and disposed of on family trips. Makes for less laundry upon coming home. We also threw away the oldest suitcase, then placed a smaller suitcase inside a larger empty one. Easy travels.


In total, the trip cost $2522.49 over six days. Divide by four people, that’s $105.08 per person per day, inclusive of everything.

Final Thoughts

This was my first vacation since taking my parents to Belize & Costa Rica 2.5 years ago. I’ve been promising my parents that I’d take them around the world. I aim to be more consistent and take them on a trip once a year.

3 thoughts on “East Coast Vacation: DC, Philly, NY, New Haven, and Boston.”

  1. That sounded like an awesome family trip Andy! You’re such a good son/friend/tour guide. LOL. It’s very cool your family is oriented towards maximizing the trip experience while minimizing everything else. If I had to choose one word to describe this trip, it would be “efficient!” I can’t believe you actually pulled off your method of “traveling light” like that. I won’t say how, just in case anyone jumps to the comments before reading the whole thing. But that must have been a relieving feeling. I would love to do the same one day.

    By the way, did the $30.99 burger or $46.82 burger taste better? Hahaha thanks for sharing man.


    1. Lawrence my friend, thanks for reading and the comment! The $30.99 burger tasted better. It had both avocados AND asparagus inside, way better than NY which was seriously just a small cheeseburger.

      Liked by 1 person

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