5-Day Itinerary to Washington DC

Five days is the perfect amount of time to soak up Washington DC. Museums alone could fill that but having a longer visit leaves room for day trips and taking your time. DC has plenty to offer from historical sites and buildings to restaurants and shopping. Regardless of your interests, there's something for everyone. Having spent quite some time in DC, I've put together an itinerary for a 5-day trip that includes everything from sightseeing to day trips. Grab a pen for notes, and keep reading…

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3 Day Itinerary | Washington, DC

Quick trips are great for limited budgets but time can be an enemy. In planning a trip, it’s important to maximize the time that is available. Washington DC is full of things to see and do, so many that it can be intimidating at first, but planning is not as hard as it might seem. For starters, many things need advance planning since reservations come recommended. Second, many of the things will be similar in content: museums, memorials, tours, etc. Rather than a traditional itinerary post where we give a recommended schedule of events, we’ve put together a series of suggested activities for art lovers, history buffs and outdoor adventurers. There are also a few recommendations towards the end to pop in if you want to go off topic. Keep reading for more!

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From portraits to sculptures to magazine covers, there are plenty of options throughout Washington DC to fill the time with art-focused activities. The trick is to determine what you are most interested in and prioritize time for your top picks. The National Gallery of Art would have been my first choice if I did much art viewing. The National Portrait Gallery would have also been towards the top of my list.

Day 1: Tackle the Big Stuff
The National Gallery of Art, Hirshhorn Museum and Sculpture Garden, Smithsonian American Art Museum and Phillips Museum have some of the largest collections of art in Washington DC. It’s where many mainstream masterpieces are held like those from Picasso, Renoir and da Vinci. Other than hosting some of the more well-known artwork, these museums each take a chunk of time. You won’t be able to fit all four into your day so it would make the most sense to choose one or two and enjoy yourself. All but the Phillips Museum are located along the National Mall so if you choose any of these three, stop at the Garden Cafe for a bite to eat.

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Day 2: Dive into Culture
One of the unique things about Washington DC is the number of cultural art museums to visit. See artifacts from sub-saharan Africa at the National Museum of African Art and immerse yourself in Asian art and artifacts at the Freer Gallery of Art and Arthur M. Sackler Gallery. The Hillwood Estate, Museum & Gardens is home to a personal collection from Marjorie Merriweather Post who was passionate about French and imperial Russian art. The gardens are gorgeous if you can fit an hour or so into your schedule to walk through.

Day 3: Get Specific
DC has a variety of art museums that exhibit specific types of media. The National Portrait Gallery consists solely of portraits from presidents to public figures and celebrities. The National Museum of Women in the Arts hosts only artwork created by women with more than 5,000 pieces. The National Geographic Museum has an exhibit featuring all the magazine covers the publication has printed as well as exhibits featuring explorations, cultures and more.

History is everywhere in DC. From monuments to archived papers, there is a piece of history almost everywhere you step. It’s also where some of the more tourist-heavy traffic will be. After all, what’s traveling if you’re not waiting in line at least once? With there being so much history to experience in DC, it can be tricky to fit everything in only three days. So this itinerary breaks each day into specific themes: top tourist spots, museums, and special interest. If memorials are important to you, you might want to sacrifice one day or at least a half day of other activities to check a few off the list.

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Day 1: Top Historical Tourist Sites
The good thing about many of these spots, reservations are either required or recommended in advance so it makes it a little easier to plan your day. The bad thing, they will take up a good fraction of the day and lines might suck up even more time. This reason alone is why it’s good to get these activities in the first day. It leaves two more to cram as much in as possible. The two big ones that take reservations are tours of the White House and the Capitol Building. The White House requires reservations and a screening process in advance. If this isn’t planned ahead, you won’t be able to do it. The Capitol Building does not require reservations but they are recommended. Availability for day-of tickets are scattered and unpredictable at best. If the Capitol Building is important to you, book the reservation in advance. Other sites to consider for your first day include the Library of Congress, Arlington National Cemetery, the Lincoln Memorial, Jefferson Memorial, Washington Monument, memorials honoring wars and their veterans, and Ford’s Theatre among others.

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Day 2: Museums
There are several history museums in Washington DC, five of which I go into detail in this post. A few of the larger ones include the National Museum of American History and the National Museum of Natural History. For a deeper dive into specific cultures, visit the new National Museum of African American History and Culture or the National Museum of the American Indian. Have a little fun at the International Spy Museum which takes a look at espionage throughout civilization or get a somber lesson in history at the US Holocaust Memorial Museum. Depending on the museum, it can take a few hours or half a day to make it through. The National Museum of American History took me about three hours and I didn’t hit all the exhibits thoroughly.

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Day 3: Specific Interests
Similar to the art available in DC, there are also places to visit that cover specific historical topics. The Folger-Shakespeare Library has a special collection from William Shakespeare and hosts performances regularly. The Newseum features exhibits that focus on media and journalism from over the years. For those who love old documents and history by paper, the National Archives will provide an interesting visit. You'll feel like Nicholas Cage in National Treasure. This is also a good day to fit in any sites or museums from the first two days there wasn’t enough time for.

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From rivers to forests, there is plenty to do for those who enjoy the outdoors. Paddle Boating along the canal and hiking are just two things to plan ahead for to enjoy nature in the capitol. Explore nature by exhibit with visits to the American Museum of Natural History or the Botanical Gardens. With a milder climate, DC makes it easy to enjoy these activities almost all year round.

Day 1: Natural History & Sites
Experience cherry trees in spring unlike anywhere else at the United States National Arboretum or become an expert on flowers at the US Botanical Gardens. Get educated on the history of nature from extinct dinosaur age animals to prehistoric plant life at the American Museum of Natural History. Take a stroll through a smaller, private garden at the Tudor House for a relaxing afternoon.

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Day 2: Take a Trip To Georgetown and Explore the C&O Canal
The Chesapeake & Ohio Canal (C&O) is almost completely intact from the original build providing an authentic historical experience. Walking or cycling is available for free along the canal or rent boats for a canoe or paddle boat ride on the water. The scenery is gorgeous and the canal is a whopping 185 miles so there’s plenty to explore.

Day 3: Hike
There are many places to go for a hike around Washington DC but one of the most popular is Rock Creek Park. There are miles to run or bike as well as horse riding activities, tennis courts, golf courses and more. The national park has activities and tours for kids and adults for those interested in expert-led experiences. To get farther out of the city, Fort Dupont Park is an old Civil War fort with hundreds of acres of land for recreation, hiking and more. It includes a long trail, community garden and even hosts concerts and events during the warmer months. Great Falls Park is another great option for hiking and boasts beautiful views of the Potomac River flowing over rocks and cliffs.

Mix up the schedule by adding in a few random activities. The National Air & Space Museum is a favorite for visitors featuring airplanes, simulations and all kinds of interactive activities. Eastern Market on Capitol Hill is a fun indoor/outdoor market that opens weekly with artisans from all over selling anything from clothing to food. Walk through the National Mall whether it’s on the way to get from one museum to another or simply to enjoy the scenery. It’s a large expanse of greenery and there’s plenty to wander around and do. If you’re on a budget, check out our post sharing free things to do in DC. For other ideas on what to do while visiting, visit our post sharing six things you must do.

4 Things To Know About Washington DC

Washington D.C. has a lot of ground to cover. It’s already a large city in size so when you take into factor all the things that are squeezed into it, it’s only natural if your eyes bug out. So whether you’re visiting DC for the first time or you’re making a return visit, we’ve come up with a few things to know before visiting. Among the four notes we share below, it’s also good to remember to wear comfortable walking shoes and don’t be afraid to venture off course. Some of the best finds are when you wander down a street that looks interesting isn’t necessarily on your itinerary. Ready? Let’s go!

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1 - Don’t try to conquer everything. This one may be obvious considering the sheer number of things to do in DC but it’s worth mentioning. There are dozens of museums, hundreds of monuments and memorials not to mention the endless list of other attractions from restaurants to mansions to theaters. The list is endless. Instead of trying to conquer as much as you can, sketch out a plan. It doesn’t need to be a crazy itinerary but it’s good to have some kind of organized to-do list for each day. Focus on what you’re most interested in and work your way through the list.

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2 - The National Mall is much larger than it seems. This one I learned the hard way so I’m passing on my misgivings to you. For starters, it’s over 2 miles long and consists of everything from the Smithsonian museums to the Jefferson Memorial. I had thought I’d be able to conquer it in a day. This ambitious thought cost me half the mall. Plan to conquer it in two days, at least if you want to actually spend time at some of the spots along the mall. Take one day to go from the Capitol Building to the Washington Monument. Take another day to explore from the Washington Monument to the White House to the Lincoln Memorial. Don’t forget the Jefferson Memorial but because it’s kind of off on it’s own, figure out where to fit it into your itinerary best.

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3 - You need to schedule a lot in advance. I am all for having a flexible itinerary but Washington DC requires at least a little bit of structure in terms of advance tickets and appointments. The White House requires advance reservations and also comes with a slew of paperwork and red tape to go through in order to be granted a visit. Many buildings and institutions don’t require advance reservations or tickets but suggest them. A few of these include the Capitol Building, the Holocaust Museum, the Ford Theatre, the Spy Museum...among others. If you are dead set on hitting some of the more popular destinations, buy your tickets now and claim a reservation now. Do not wait. We looked at tour availability for the Capitol Building through December and open time slots are are limited some weeks and scattered others. Book now, people.

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4 - Certain sites need day trips or close to it. I’m thinking of three destinations in particular: Georgetown, Mount Vernon and Arlington Cemetery. Arlington is the closest to DC, just over the Potomac River but it is so massive you want to leave yourself enough time to hit all the sites you are most likely looking forward to. Georgetown is within DC but it might as well be a town of it’s own. There is plenty to see and do and if you’d like to walk or bike along the C&O Canal or take a canoe down the Potomac, you’ll definitely need the whole day. Finally, Mount Vernon is about a 30-60 minute drive from DC pending traffic. Washington’s estate is a popular spot among tourists and rightfully so. Just don’t plan much for the rest of your day if you want to actually enjoy it.

5 Day Boston Itinerary

With a few extra days in a trip, you can afford to take your time seeing the sites. While that may be nice, you also don’t want to waste any time. The trick is to find a nice balance so you cover a lot of ground without feeling rushed or overwhelmed. Being a walkable city, Boston makes that easy. And if a destination happens to be a little too far for walking, their public transportation system has you covered. Keep reading while we take you through a five-day trip in Boston.

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DAY 1: The Natural Side of Boston
Your first day in any city should always have flexible plans. You never know what delays you’ll run into and then there’s always traffic. Isn’t that fun? Assuming your first day has at least a few hours to explore, go without a specific plan. Visit the Boston Common and the Esplanade. Both are open to the public and have plenty to see and do. It’s an easy way to get your trip started and they should be on your Boston bucket list anyway.

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DAY 2: Embrace Your Inner Tourist
Let go of all the negative connotations that come with being a “tourist” and embrace it for a day. Every city, including Boston, is full of sites that are considered tourist attractions. Chicago has Navy Pier, Boston has the USS Constitution. Chicago has Millennium Park, Boston has the Boston Common. Chicago has Lou Malnati’s, Boston has Neptune’s Oyster Bar. I could go on for days. To encourage tourist behavior even more, we recently shared 8 tourist spots to visit in Boston. This includes the Cheers Restaurant and Fenway Park among other popular destinations you will find groups of tourists visiting.

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This is also a great day to visit a few monumental sites like the JFK Library & Museum, USS Constitution or Museum of Fine Arts. A few tips to keep in mind, do a little research before you go. Make sure you know the hours of the locations you’d like to browse around like museums and historical sites. Find out what their entrance fees are, if there are any tours available and buy tickets in advance for everything that you can. This will save you lots of time and it will usually guarantee your entry.

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DAY 3: Day Trip to Cambridge
Even in our three-day guide to Boston, I still included a trip to Cambridge. This neighbor city is a gem all on its own. With the Harvard and MIT campuses located here, it’s full of lively coffee shops, restaurants, bars and town squares. Walk through the Harvard Yard, take a photo on the steps of the Widener Library, enjoy one of the many museums from archaeology to art. Take a tour of the Harvard campus led by students, grab a cup of coffee in one of the local cafes and reflect on what you’ve seen and done in Boston so far. It’s a great place to pretend like you’re a local and just enjoy the beautiful day.

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For the history lovers, take a walk over to the Longfellow House - Washington’s National Headquarters. This gorgeous historical home takes tours through late October/early November before closing for the season. Grab photos of Memorial Church which has a beautiful architectural design before a bite to eat at one of Cambridge’s many restaurants. Check out our recommendations in our Cambridge Neighborhood Guide.

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DAY 4: Walk the Freedom Trail
This is the ultimate tour of Boston. It takes you through all the hottest spots in the city including the sites with the most historical significance. It’s also a great route to deviate off of in case you want to see extra sites like Acorn Street. The tour itself is free and will take you through the North End, Downtown and Beacon Hill neighborhoods. Most of the sites are free like the Granary Burying Ground, Boston Common and many churches. You can view all of them and grab photos but several like the Paul Revere House cost an admittance fee.

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Do a little research beforehand to create a route that suits your interests and allows you to veer off course if you’d like. This is also a great time to check out any of the freedom trail destinations that allow you to explore inside. Check out their hours and if there are any admittance fees so you can budget both time and money. Again, anything that you can purchase in advance is ideal so you can skip potential lines and save time.

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DAY 5: Eat Your Way Through the North End
I can’t think of a better way to end a trip than eating your way through an Italian neighborhood. Am I right? The North End has everything from Neptune’s Oyster Bar to traditional white tablecloth Italian restaurants and pastries so divine and indulgent, you’ll feel guilty for weeks. If you’re lucky enough to walk through on the weekends, they have a farmer’s market in the morning with all kinds of produce and fish that were caught that morning. Being a Midwestern native, this is something I have never seen before so it was pretty cool.

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A few recommendations while you’re eating your way through the North End. Grab coffee at Thinking Cup. This local coffee shop has incredible lattes and cappuccinos and there’s a ton of space to sit down and take your time. Grab some pizza at Umberto’s Galleria or Locale. They’re two different experiences so it depends on what you’re looking for. Umberto’s has traditional Sicilian-style pizza offered first come-first serve during lunch and is cash-only. Locale is a more trendy pizza joint with equally tasty pizzas that have every topping you can imagine plus appetizers and a great drink list. Grab some sweets at Mike’s Pastries but be ready to wait in line. If you still have room left, head over to La Galleria 33 for mind-blowing pasta. As far as I’m concerned, you haven’t had Italian until you’ve had pasta.

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