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How to Spend a Weekend in Washington, D.C.

How to Spend a Weekend in Washington, D.C.

Every American (or non!) should spend at least one weekend in Washington, DC. It’s the United State’s capital, after all! There is so much to see, do, eat, and explore in this melting pot of a city. Let’s dive into the weekend itinerary for DC!

Table of Contents

  • Friday
    • Firehook Bakery
    • Founding Farmers
    • The White House
    • Hank’s Oyster Bar
  • Saturday
    • Mission Dupont
    • Explore Georgetown
    • Proper 21
  • Sunday
    • Duke’s Grocery
    • Captain Cookie and the Milkman

Friday

Firehook Bakery

DC has so many incredible bakeries and cafes. Obviously it is not possible to see all of them nearby Firehook Bakery. It’s a cute, tiny corner cafe with people coming and going all morning. They have a huge array of croissants, breakfast sandwiches, quiche, pastries, etc. to choose from. After taking an embarrassingly long amount of time to choose breakfast, I eventually settled on a spinach and tomato mini quiche and my brother chose the ham and cheese croissant. They were yum!

Unfortunately, we both had to cram in a working session in the morning. We posted up in his kitchen, made some more coffee (shout-out to Kauai Vanilla Macadamia Nut coffee), and cranked out our work so we could wrap up by lunch and enjoy the rest of our weekend in Washington, DC!

Founding Farmers

I was excited to head to Founding Farmers for lunch as several friends recommended this place. We made reservations ahead to ensure a great spot outside on the patio. This was definitely one of the spots to be seen at! Diplomats and other political figures (note: I’m actually not sure about this; I’m just assuming anyone wearing a suit walking around in DC is in politics at this point) were filing in and out. Even for our late lunch the patio was full.

Founding Farmers meal on the patio

After lunch, we made our way a few blocks south so we could spend the next hours wandering past the various monuments. The weather was stunning and the blue skies made for a perfect backdrop in our pictures. Again, I only had the weekend in DC so we power-walked to see as much as humanly possible!

If you have additional time, be sure to check out the vast list of museums. Conveniently, most are all along the same stretch between Constitution Ave and Independence Ave. Almost all were closed while we were there (thank you, Covid). However, if you find yourself fortunate to be back once this pandemic has past, friends in DC recommended the following: The Renwick, an art gallery right by the White House and the Hirshhorn, a Smithsonian museum of modern art.

The White House

Finally, we made our way to The White House. Keep in mind this visit was in October 2020, about a month before the US election. As one could expect, a plethora of extremists from either political party were out front screaming at each other into megaphones. For a people-watcher like myself, this was gold. We stood around watching the scene unfold as various reporters started to approach the crowd.

Suddenly a reporter came up to us and asked if we could answer a few questions on camera. Before I could say no, Joe quickly agreed and suddenly the camera and microphone were right up in our faces. We proceeded to get interviewed in front of the White House regarding President Trump’s recent positive coronavirus test. Turns out our interviewer was from Australian News and we made the final cut. In fact, my girlfriend who lives in Australia messaged me to tell me she saw us! When in DC….

We are ~famous~

After becoming celebrities, we took a pitstop back at home to grab some more coffee so we wouldn’t crash. I checked my phone and we were already well over 25,000 steps for the day! Then we were ready to head down the street to dinner at Hank’s. Yes, literally three down the street! I told you Dupont is a great neighborhood.

Hank’s Oyster Bar

I am now convinced you can’t spend a weekend in DC without eating at Hank’s Oyster Bar. Again, we were able to sit outside on the patio and it was a great place to watch everyone stroll by. We ordered the crab dip as a starter. Wow! It came out steaming and literally melted in our mouths. Somehow we maintained some form of self control to prevent ourselves form inhaling the entire thing before our actual meals arrived.

A weekend in Washington DC is not complete without a visit to Hank’s

We ordered our meals and shortly after I proceeded to eat the most delicious shrimp Po’ Boy sandwich of my life. Seriously it was incredible. Delectable. I’m drooling remembering it. Good food, good drinks, catching up with family – can’t beat it!

Saturday

Mission Dupont

DC is well-known for its popular bottomless brunches that seem to be offered at almost every restaurant. Essentially you pay an upfront fee (usually around $25-30) and get unlimited alcohol. And it’s a marathon, not a sprint, people! Therefore, since I was checking off everything to do during my weekend in Washington DC, we booked a bottomless brunch! Twist my arm…

My brother secured a morning reservation for us at Mission Dupont. The food was incredible. I ordered the Breakfast Quesadilla with chorizo and it was massive – I could only eat half! It was so delicious though. My brother ordered the Breakfast Burrito and also verified it was delicious. We cooled off with some Bloody Mary’s and margaritas. The theme of the weekend continued: amazing food, amazing drinks, amazing vibes.

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Explore Georgetown

After lunch we walked toward Georgetown to explore M Street. They have everything here! The store fronts were super cute and we walked in and out exploring them all. Then we grabbed a coffee and sat near the river. It was a beautiful afternoon and boats were chugging past us. Eventually, we peeled ourselves away from the scene and wandered back toward Dupont.

Proper 21

By dinnertime, I was still stuffed from my quesadilla and did not have much of an appetite. However, I am never one to waste a Saturday night, especially in a new city! My brother and I wandered up and down some streets until we found a place we could eat outside that had people. We ended up stumbling upon Proper 21.

I texted a friend who lives outside of the city since I knew he had dinner nearby. He and his wife joined us for a drink and it was great to see my brother gain some connections with other people in the city. They gave him the low-down of some of the neighborhoods and some of the restaurants and bars and their stereotypes.

Old friends in new cities!

Sunday

Sunday morning we took a long stroll past other neighborhoods. We started in Cardozo and checked out the shops and restaurants on U Street and 14th Street. Then we wandered north through Meridian Park toward the Mt Pleasant neighborhood. I could’ve walked all day! It was nice to see more of the residential side of the city.

Stumbling upon different murals in DC – RIP RBG!

We then wandered back down to Embassy Row. I loved walking past the different buildings and trying to test myself to see if I knew which embassy it was based on the flag.

Duke’s Grocery

Our final meal was at Duke’s Grocery. I actually skipped breakfast because I heard so much hype about this burger and wanted to inhale the entire thing. Duke’s Proper Burger has consistently won “best burger in DC” for years, so I couldn’t wait to judge it myself. My brother opted for the pastrami sandwich.

The burger arrived and my mouth watered just looking at it. The first bite was heavenly. The burger really did live up to the commotion! Music was bumping and the restaurant had a super fun vibe.

Captain Cookie and the Milkman

My one last pit stop before we left was to check-out Captain Cookie and the Milkman. Although I was stuffed from the burger, I heard this was the Diddy Riese of DC (a famous ice cream cookie sandwich stop in LA). I ordered my cookie sandwich: chocolate chip cookie, snickerdoodle cookie, and chocolate ice cream.

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A post shared by Captain Cookie (@captaincookiedc)

Admittedly, the cookie itself was pretty hard. Like rock hard to the point I almost snapped my tooth off. The ice cream was delicious though! I ended up just eating the ice cream and throwing the cookie pieces away. Oh well, I can at least check that off the list.

The weekend flew by much too fast, but gave me such a great taste of the offerings in DC! I loved the various neighborhoods, the international flair, the history sprinkled in around each corner. I will hopefully return soon to spend longer than just a weekend in DC!

Check out some other fun, US city guides:

  • A Quick Guide to New Orleans, LA
  • How to Spend a Weekend in San Francisco, California
  • The Best Piano Bars in Chicago

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DestinationsItineraries & GuidesTravelUSAWashington DC
About Sara

About Sara

I’m an American who quit my job in Chicago to seek out an Italian adventure. I currently live and work in Milan, Italy.

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About Me

About Me

Sara in Italia, Italophile

Ciao! I'm Sara. An American who quit her job in the US and moved to Milan to seek out my journey of La Dolce Vita. Follow along for Italy guides, tips, and general rants about the pros and cons of moving to Italy.

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Follow along as I try to figure out my life abroad 🇮🇹

Sights and sounds from a Sorrento summer. 🌀 . . . Sights and sounds from a Sorrento summer. 🌀
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