Part 1: Boston – New York – Washington D.C. in Two Weeks, 3 Part Series
Part 1 – Trip Overview and 4 Nights in Boston
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Getting Around via Amtrak
Visiting three iconic cities in one trip - Boston, New York City, and Washington D.C. - is a well-connected and convenient experience. With a train option available, exploring these vibrant destinations is not as challenging as one might think. You can easily fly into Boston or Washington D.C. and plan your itinerary accordingly. You have the option to either start in Boston and make your way down to Washington D.C., or vice versa. Amtrak provides a reliable intercity rail service, allowing you to travel comfortably from Boston to New York City's Moynihan or Penn Station. From there, you can continue your journey by catching another train from New York City to Union Station in Washington D.C. With this seamless combination of flights and trains, you can take on an unforgettable trip filled with rich history.
Summary
Our Proposed Itinerary - The Best of the East Coast
Accommodations
Getting Around Boston
Day 1 - Arrival Day
Day 2 - Freedom Trail
Day 3 - Other Things to Do Around Boston, including a list for Kids
Day 4 - Concord, Massachusetts
Day 5 - Departure, Leave for New York City via Train
Our Proposed Itinerary - The Best of the East Coast
Our proposed itinerary encompasses the best of the East Coast. Starting with four nights in Boston, visitors can explore the historic Freedom Trail, stroll through the charming neighborhoods, and discover Concord, Massachusetts. Moving on to New York City for a five-night stay, the options are endless. From famous landmarks like Times Square and Central Park to world-class museums and Broadway shows, the city offers a wealth of cultural experiences. The itinerary concludes with four nights in Washington D.C., where visitors can visit the monuments and memorials, explore the Smithsonian museums, and dive into the political history of the nation's capital. Whether you choose to extend your stay or modify the number of nights in each city, this itinerary is an exciting journey through some of America's most visited destinations.
In summary: 4 nights in Boston, 5 nights in New York City, and 4 nights in Washington D.C.
I will break down this post into 3 parts, to make it easier to read and absorb in chunks.
BOSTON
Accommodations
VRBO might be the ideal choice for you if you're traveling with your family. A home away from home experience, complete with a kitchen and living spaces might just be what you need. Having the convenience of a kitchen allows you to prepare meals and save money while still enjoying quality time together. We stayed in Medford and took the train into the city. On the other hand, for smaller groups or individuals who prefer having their own space, a hotel can be a more comfortable and convenient option, especially if you're staying in the city. Hotels offer amenities such as daily housekeeping, concierge services, and convenient locations that can enhance your overall travel experience.
Getting Around Boston
Boston has an excellent public transit system, making it unnecessary to rent a car during your visit. With its extensive network of subway lines and buses, getting around the city is a breeze, so not only will you save money on car rental fees, but you'll also avoid the exorbitant costs of parking in Boston. However, we do recommend visiting Concorde, Massachusetts, as one of our things to do. We do recommend renting a car for that specific day. Alternatively, taking a guided tour is a viable option, and it may turn out to be a more cost-effective choice as well.
Itinerary - Things to do in Boston
DAY 1 ARRIVAL DAY
Depending on what time you arrive and from where, you might be feeling a bit jet lagged. If you’re arriving early and staying within the city of Boston, I suggest taking it easy and exploring your immediate surroundings. If you’re arriving early, you might want to schedule an evening tour, giving you a rest in the afternoon if you’re coming from a far away destination. If your flight is not that long, schedule a tour for the afternoon that would suit your schedule. At any rate, our first suggestion is to explore your immediate neighborhood – get to know places to eat or places to find a good breakfast option, find the nearest public transportation stations.
If you have time, take a food history and walking tour and enjoy the seafood offerings.
DAY 2 FREEDOM TRAIL
To gain an appreciation for Boston, where the American Revolution began, the Freedom Trail tour is a must.
The Freedom Trail is a journey through the history of the United States. Stretching 2.5 miles, this trail leads visitors through 16 significant historical sites, telling the tale of the American Revolution. From the solemn grounds of the Massachusetts State House to the legendary Old North Church, where Paul Revere's famous lantern signal ignited the revolution, each stop on the Freedom Trail unveils a chapter of our nation's quest for liberty and independence.
With minimal time stopping at any of the sites, the trail can be completed in approximately two hours on foot. However, if you choose to stop and explore the historical sites along the way, it is sure to take longer but well worth the extra time. You can make this into a full day or break it up into two half days by taking in each site, lingering to learn more, or taking in the ambiance of the place. Some areas are in a park-like setting, ideal for a picnic. There are several places along the trail where you can linger longer to enhance your experience. So, take your time.
If you are with kids, it's important to note that the pace may slow down even further. To fully enjoy the experience with young ones, it might be wise to break up the trail into shorter segments, allowing ample time for them to frolic at the sites.
If you prefer to take a guided tour, learn more here. You may also find that the hop-on and hop-off trolley rides might also be a good option for those who get tired of walking (especially with the little ones).
Freedom Trail Self-Guided Walking Map. Make sure to open the map menu by clicking on the small box on the top left corner next to the F in the purple circle - top left corner.
DESCRIPTIONS OF EACH SITE ON FREEDOM TRAIL
Here's a list of the 16 sites along the Freedom Trail. There are Freedom Trail plaques marking each site. You can start or end anywhere along the way. For more information on each site, go here. I have included several places where you can linger longer to enhance your experience.
Freedom Trail starts at Boston Common, a beautiful park that’s perfect for a leisurely stroll or picnic. It is the oldest public park in the United States established in 1634, and it is over 40 acres of land. It is a historical site where the Puritans punished misdeeds and where the Redcoats camped out during the British occupation in 1775. Just next to the Commons is Public Garden, the country's first botanical garden, where you can admire the vibrant flowers and serene ponds. **Linger in the park for a bit – walk through the treelined paths. If you have kids, it’s a great place to play.
Massachusetts State House. Built in 1798, this historic landmark has a stunning white dome, serving as the seat of government since its construction. The architectural splendor of the State House showcases a perfect blend of Federal and Georgian styles.
Park Street Church. A historic site built in the early 19th century, once serving as a landmark for travelers coming to Boston. The Park Street Church has witnessed pivotal moments in American history, serving as a platform for influential speakers such as Martin Luther King Jr. and William Lloyd Garrison.
Granary Burying Ground. One of the oldest cemeteries in the United States, it dates to 1660 and holds the remains of many notable figures from the American Revolutionary period, including Paul Revere and Samuel Adams.
King’s Chapel & King’s Chapel Burying Ground. Built in 1754, its elegant Georgian design includes a stately bell tower and intricate stained-glass windows. It is also home to the King's Chapel Burying Ground. Established in 1630, the quaint cemetery adjacent to the chapel is the final resting place of many notable figures from Boston's past, such as John Winthrop, the first governor of Massachusetts, and Mary Chilton, one of the Mayflower passengers.
Boston Latin School/Benjamin Franklin Statue. Founded in 1635, it holds the distinction of being the first public school in America.
Old Corner Bookstore. This charming brick building, dating back to 1718, has witnessed centuries of literary brilliance and cultural significance. The Old Corner Bookstore once served as the epicenter of Boston's thriving publishing industry, publishing books by Henry Thoreau and Nathanial Hawthorne.
Old South Meeting House. Originally built as a Puritan meeting house in 1729, played a role in how the Boston Tea Party began. It was here, on a fateful evening in December 1773, that the colonists gathered to protest the oppressive taxes imposed upon them by the British crown. The discussions held on that night eventually erupted into an act of defiance as crates of tea were dumped into the nearby Boston Harbor. Another must-visit site along the Freedom Trail is the Boston Tea Party Ships & Museum. Take a tour and see a reenactment of the historical events that led to the American Revolution and even throw a crate of "tea" overboard (taxes without representation! Huzzah!).
Old State House. Constructed in 1713, this building is where heated debates over liberty and self-governance took place, leading up to the American Revolution.
Boston Massacre Site. On the evening of March 5, 1770, tension between British soldiers and American colonists reached a boiling point, culminating in a tragic incident that would forever be remembered as the Boston Massacre. Today, visitors can stand where the first sparks of revolution were ignited and pay tribute to the lives lost in the pursuit of freedom.
Faneuil Hall served as a meeting place for revolutionaries during the early days of the nation. Today, it continues to buzz with energy as a bustling marketplace, lined with a variety of shops, restaurants, and street performers. Just steps away from Faneuil Hall, a historic marketplace where revolutionary speeches were once delivered, is the Boston Public Market, a year-round indoor market that showcases an array of fresh produce, cured meats, artisan cheese, and specialty products. It's a great spot to grab a snack or sample local delicacies. There is also the Greenway Carousel near Faneuil Hall that the kids might enjoy.
Paul Revere House – worth going in and taking a tour. Built in 1680, this wooden structure served as the former residence of the renowned patriot, Paul Revere. Visit the Paul Revere Museum to learn about the famous midnight rider and his role in the revolution.
Old North Church. With its elegant Georgian architecture and white steeple, this building dates back to 1723, making it the oldest standing church in Boston. It was from the Old North Church's tower that two lanterns were famously displayed in April 1775, signaling Paul Revere's midnight ride and alerting colonial troops of the approaching British forces. Old North Church is in the North End, so be sure to explore Little Italy, where you can savor delicious Italian cuisine and experience the vibrant culture of this historic neighborhood.
Copp’s Hill Burying Ground. Dating back to the late 17th century, it is one of the oldest cemeteries in Boston and serves as the final resting place for many residents from the North End.
USS Constitution. Commonly known as "Old Ironsides," launched in 1797, stands as the oldest commissioned warship. This majestic three-masted frigate has weathered numerous battles, including the War of 1812, famously defeating several British warships. Today, the USS Constitution serves as a floating museum.
Bunker Hill Monument. This granite obelisk commemorates the Battle of Bunker Hill, one of the early clashes in the American Revolutionary War. Completed in 1843, it serves as a reminder of the sacrifice and resilience of those who fought for liberty and independence.
DAY 3 OTHER THINGS TO DO
Harvard University Tour and stroll around Cambridge. On your tour, you'll have the opportunity to visit historic landmarks like Harvard Yard. Or you can take a stroll along the Charles River and enjoy the views of the city skyline. Explore the vibrant streets of Cambridge, filled with cozy cafes, quirky bookstores, and lively street performers.
Fenway Park Tour. Fenway Park is the oldest ballpark in the Major League Baseball, having opened in 1912. It has been the home of the Boston Red Sox since it opened. The park offers tours for fans and tourists, providing an opportunity to learn about the park's history and get up close to its most famous features. Take the Green Line B,C, and D to Fenway Park (see our guide on Boston’s Public Transportation); Green Line E does not stop at Fenway Park.
Museum of Fine Arts. Notable for its diverse collection of American art (including a significant number of pieces from the Colonial and American Revolutionary War periods), European paintings (Degas, VanGogh, Rembrandt, Renoir, and more), Asian and Egyptian collections, and more.
Isabella Steward Gardner Museum. The museum houses an art collection of world importance, including Titian, Manet, Boticelli, and many more. The collection is displayed in a historic building fashioned after 15th century Venetian palace with a lushly planted courtyard that is a significant aesthetic of the museum.
JFK Presidential Museum and Library. The museum holds all the original papers of the Kennedy Administration, as well as special materials, such as books and other publications that President Kennedy and his family had. The museum has permanent exhibits on President Kennedy’s time in office, including the race to space and his public campaigns.
Boston Public Library. The McKim Building of the Boston Public Library is a National Historic Landmark and is listed on the National Register of Historic Places. The library has significant collections of rare books and manuscripts, maps, prints, and a wealth of other resources. This includes the personal library of President John Adams and early Shakespeare editions.
Stroll around the Waterfront
For Kids
Children’s Museum. Established in 1913, it is the second-oldest children's museum in the United States. The museum is located on Children's Wharf along the Fort Point Channel in Boston and is recognized for its emphasis on an interactive approach to learning. The museum also offers various educational programs and workshops that encourage creativity and critical thinking.
New England Zoo. Located in Boston's historic Franklin Park, features a variety of exhibits, including the Tropical Forest, which houses gorillas, lemurs, and many other species; Serengeti Crossing, featuring zebras and ostriches; Kalahari Kingdom, home to lions; and the Giraffe Savannah, where visitors can view giraffes and zebras. There is also a butterfly garden, a bird's world exhibit, and a children's zoo. The zoo is dedicated to conservation and education, with interactive exhibits and informative presentations that shed light on the importance of preserving our planet's biodiversity.
New England Aquarium. A must-visit for all marine life enthusiasts. From the massive Giant Ocean Tank, where you can spot sea turtles, stingrays, and even sharks, to the Penguin Colony, where you can watch these adorable creatures waddle and swim, there's something for everyone. The aquarium also focuses on conservation and education, providing valuable insight into the importance of protecting our oceans.
DAY 4 CONCORD MASSACHUSETTS
We highly recommend visiting Concord, Massachusetts for a full day. Immerse yourself in the rich history and literary legacy of Concord, Massachusetts, a charming town overflowing with literary tales from the past. You can do it on your own or take a guided tour.
Begin your day by stepping into the hallowed grounds of the Minute Man National Historical Park, where the echoes of the American Revolution still resonate. Stroll or bike through the paths, where brave patriots once stood in defense of their cherished ideals. Make sure to read the plaques along the path to learn about the Revolutionary War.
Discover the legendary North Bridge, forever etched in history as the site where the famous "shot heard 'round the world" (a phrase coined by Emerson, we learned) was fired. And just right next to it is “The Old Manse,” home to Emerson’s grandfather and later to Ralph Waldo Emerson and Nathaniel Hawthorne.
The Manse.
Venture into the heart of the town, where quaint streets lined with historic homes and shops beckon you to explore their treasures. Stop by the Ralph Waldo Emerson House, the former home of the renowned philosopher, and dive into the profound wisdom that emanated from this literary haven.
Ralph Waldo Emerson’s House.
No visit to Concord would be complete without a visit to the well-known Orchard House, the residence of Louisa May Alcott, where she penned the much-beloved novel "Little Women." Step into the pages of this literary masterpiece as you wander through the rooms that inspired some of the greatest works in American literature.
Orchard House
For those seeking a deeper connection with nature, make your way to Walden Pond, immortalized by Henry David Thoreau through his writings. Breathe in the serenity that Thoreau once cherished and find solace in the simplicity of nature, just as he did during his renowned experiment in self-reliance.
Walden Pond.
DAY 5 – LEAVE FOR NEW YORK CITY VIA TRAIN… TO BE CONTINUED.
This concludes our Boston leg of the journey. Take the Amtrak train from Boston North or South Station to New York City’s Moynihan Station. Our comprehensive Destination Guide to New York City includes information on how to use the public transportation. We’re now headed to New York City on Day 5 of our 3-part series on BOSTON – NEW YORK – WASHINGTON D.C. in TWO WEEKS.
In the meantime, Happy Travels!
Zellie, your forever a traveler.
