A historic and walkable New England city, Boston makes for a great 4 day getaway. It is easy to get to from NYC, with plenty of places to stay in, dine at, and explore. You can be as active as you want, maybe running the half marathon “A Run to Remember” honoring Boston’s first responders like my friend did, or you can be relaxed and spend an afternoon basking in the sun on the Charles River Esplanade, followed by dinner in Beacon Hill. You can be a romantic, floating through the Boston Common in a Swan Boat. How about catching a Red Sox baseball game at Fenway Park? You can definitely be an American history buff, with sites like the Paul Revere House and Faneuil Hall along the Freedom Trail telling the story of the American Revolution.
Boston is divided up into neighborhoods making it easy to navigate around, especially if you get comfortable with their public transit system, the MBTA or “T” Subway system.
We’ve gone to Boston twice on long weekend trips (so far). . . so here I condense the best of what we saw into an engaging 4 day itinerary.
Day 1 – Arrival and Fenway Park
Giving yourselves travel time during the day, time to catch a bite to eat and settle into the place where you will be staying, the next order of business is to catch an afternoon Red Sox game in Fenway Park.
Fenway Park
What a treat to see a Red Sox game! Just taking the train over there and watching baseball fans packed into the car with their caps and jerseys, already getting hyped up for the game, was amazing. We got tickets for fairly decent seats in advance, but got there a little late, about into the sixth inning.
Lucky for us, no one had scored yet. We got pretzels and beer at the concession stand, and as we settled into our seats the game really took off with the Red Sox scoring and winning the game in a very intense ninth inning. On our way out of the stadium, trying to make our way through the bustling crowd, we spotted the pitcher Valdez exiting in his fiery red convertible with the crowd cheering him on!
Hungry and a little strung out after a long day of traveling and the excitement of the game, I was more than ready to settle into a good place to eat. There are a number of places nearby, and we decided on The Yard House [126 Brookline Avenue, (617) 236-4083]. Admittedly it had a noisy atmosphere with tons of people conversing at the bar, so we tried to get a table a little bit away from the crowd. The food was very good, I chowed down on my burger like it was my last meal. Another beer hit the spot too. Then it was off to get a good night’s sleep before a big day of seeing the sights of Boston.
Day 2 – The Boston Common and a History Lesson
The Boston Common
This is America’s oldest public park, founded in 1634. The Boston Common has seen all of American History – it is where militia of the American Revolution dealt with the British Red Coats who were encamped on the grounds in 1768. George Washington came here to celebrate the nation’s Independence. The park has seen the Civil War, World Wars I and II, the Vietnam war and the ongoing fight to protect civil liberties. On Memorial Day weekend in 2019, the city commemorated service members by placing a flag in the ground for each Bostonian service member who lost their lives fighting in a war – more than 37,000 flags were placed into the ground at Boston Common.
The Freedom Trail
At the park’s visitor’s center you will find the beginning of the Freedom Trail, which is a great introduction to the history of Boston. This trail covers 16 important historical sites that take you from the Boston Common, through Faneuil Hall and Quincy Market, The Old North Church, the North End neighborhood, the USS Constitution and Museum all the way to the Bunker Hill monument.
It can be walked in about two hours or more, depending of course on how often you stop and spend time at each of the sites. See my post on our experience of The Freedom Trail – Boston, MA and to get more information.
If you want to grab lunch at a historic landmark before you go, you can head over to Cheers [84 Beacon Street, (617) 227-9605] for some food, fun and nostalgia.
The Swan Boats
A sweet thing to do before you leave the Boston Common is to take a ride on the lagoon on a Swan Boat. Bostonians used to be able to take out small rowboats themselves, but in 1970 a man named Robert Paget decided to introduce a paddle boat built with a swan constructed on it that he let people ride on for a fee. The idea was based on the romantic German opera Lohengrin, where a knight of the Grail crosses a river in a boat drawn by a Swan to defend the innocence of his heroine, Princess Elsa. The Paget family introduced a fleet of these paddle boats which soon replaced row boating on the lagoon. We took a ride, gliding along the surface of the water, as the edge of the boat sits nearly at water level….if you use a little (or a lot of) imagination you can feel like a swan yourself floating around on a sunny day. swanboats.com
Copley Square and Trinity Church
After the Freedom Trail, the last stop for the day might be making a right on Bolyston Street at the south of the park towards the Back Bay neighborhood and Copley Square. The Boston Marathon famously finishes here, and it is a cultural center with the Museum of Fine Arts, Museum of Natural History and the New Old South Church located here. It is also the location of Trinity Church, which dominates the square next to the towering and sleek black John Hancock high-rise building, offering a unique juxtaposition of historic and modern. Trinity Church was founded in 1733 and is open to the public. It is a stunning example of the Romanesque style. You can check out their website trinitychurchboston.org for service and concert schedules.
If you’re ready for dinner, a nice spot in the neighborhood is Met Back Bay [279 Dartmouth Street, (617) 267-0451]. We had great burgers there and they are also good for brunch.
Day 3 – Relax, Shop, Eat
After a lot of walking the day before, now is time to slow down and savor. You can start at Faneuil Hall and Quincy Market to do some shopping for souvenirs. I get my Boston T-shirts here. You can saunter around as long as you want, there’s a Starbucks for a quick bite and coffee if you need it, or stop for lunch at the over 50 places to get food. We got some decent lobster rolls at the Salty Dog Seafood Grille and Bar [206 S. Market Street, (617) 742-2094], which has great outdoor seating for people watching at the market while you eat.
Charles River Esplanade
After lunch, take a car service or the T subway over to Beacon Street and walk over to the Charles River Esplanade, an expansive green space with bike paths, canoes, and plenty of room to stretch your legs and gaze at the water. You could bring a picnic here or just nap for a few hours before dinner.
Beacon Hill
When ready, head over to Acorn street in the Beacon Hill neighborhood. A protected historic district, Beacon Hill gets its name from the beacon that used to be located on top of the hill to announce invasions to the city. It was home to many famous Americans, including Robert Frost, Sylvia Plath and Louisa May Alcott. Charles Street has antique shops and local restaurants. Acorn street is Boston’s narrowest street and is said to be its most photographed street. The centuries old cobblestones are picture worthy in themselves. A walk around the Beacon Hill neighborhood offers many opportunities for some picture taking.
For a lovely dinner on your last night in Boston, I might recommend 75 Chestnut, [75 Chestnut, (617) 227-2175]. It’s an intimate but upscale dining spot with a Mediterranean influence, and menu items such as pumpkin ravioli, Meyer lemon chicken breast with rainbow potatoes, or beef tenderloin with a peppercorn brandy cream sauce and grilled asparagus.
Day 4 – Before you leave…..
John F. Kennedy Museum
It may be tempting to sleep in before the afternoon ride home, but if you can muster the energy it’s worth it to spend the morning at the John F. Kennedy museum. It sits on a 10 acre park on the Boston waterfront near the University of Massachusetts. To get there take the T Red line to the JFK/UMASS stop. There is a free shuttle from the subway stop to the JFK library and museum. You can see a film in the theatre on the story of the Kennedy family and their rise in politics. As you walk through the museum, the rooms recreate the world of JFK for you, as do the multimedia exhibits. If you need refreshments, there’s a cafe but I enjoyed the bookstore, where I got a copy of John F. Kennedy’s book “A Nation of Immigrants”, and a DVD of Jacqueline Kennedy’s televised tour of the White House.
On the main floor a large room with floor to ceiling windows looks out onto a lawn where they have anchored a sailboat that JFK and his family used to own. As you gaze out over the water beyond the lawn, you can almost picture yourself a Kennedy running out to take a sail on their boat.
Many historic moments are anchored here in Boston, and there was a lot to think about as I read “A Nation of Immigrants” on the way home.
Top 10 Things to do in Boston
- Fenway Park
- The Boston Commons
- Swan Boats
- The Freedom Trail
- Faneuil Hall and Quincy Market
- The North End
- Copley Square and Trinity Church
- Charles River Esplanade
- Beacon Hill
- John F. Kennedy Museum
List of Books to Read Before You Go Here is a random list of some books I think would be a good read before your trip or while travelling. I have not read these books, except for the Boston Girl novel, but want to:
Common Ground: A Turbulent Decade in the Lives of Three American Families – J. Anthony Lukas (How Boston’s Landscape has changed over time.)
The North End: A Brief History of Boston’s Oldest Neighborhood – Alex R. Goldfield (A story of cultural change.)
A Short History of Boston – Robert Allison (First rate history book, with wonderful illustrations and lovingly written.)
Boston’s Freedom Trail: Trace the Path of American History – Cindi D. Pietrzyk (What it says it does)
Patriot’s Farewell: The Boston Brahmin, a Political Thriller Book – Bobby Akat (Fiction, if you like thrillers.)
The Boston Girl – Anita Diamant (Fiction, a charming novel following the growing up years of an immigrant girl living in Boston in the previous century.)
Dates of Trip:
September 2015 and May 2019
The Full Itinerary 