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2 Days in Boston: The Ultimate Boston Itinerary

May 11, 2022
Boston Massachusetts

Two Days in Boston, Massachusetts

All it takes is an Uber ride from Boston Logan Airport for it to become immediately evident that Boston is a city defined by its history and sports culture. Drive along the highway, and you’ll see countless Bostonians rowing and sailing along the Charles River. You’ll just feel the energy emanating out of Fenway Park if you happen to visit during the end of the season. Luckily, baseball playoffs coincide with the city’s fall foliage season when Boston is aglow in rich reds, yellows, and orange hues. And of course, history abounds in Boston. Boston’s main attraction is literally a walking road map that transports you back to the Revolutionary War era. Plus, major cities like Lexington and Concord are a mere 30 minutes or so away as are notable sights like Walden Pond.

While I spent three weeks exploring the city, the neighboring towns, and other parts of New England, you can get actually get quite a feel for the city with just 2 days in Boston. 

Boston Public Gardens

In this particular Boston itinerary, your first day in Boston will be dedicated to the famed Freedom Trail, which strategically takes you through all of Boston’s most famous sights. The city of Boston literally lays out the perfect roadmap for all of its best attractions; all you have to do is follow it. You’ll have a chance to better understand Boston culture the next day with a more slow paced visit to some of Boston’s most exciting and exquisitely beautiful destinations.

Shall we get started? 

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Day of History: 1 of 2 Days in Boston

Harvard University

Harvard University

While the majority of the day and night will be spent on the Freedom Trail, let’s start our morning at the most prestigious university in the United States, Harvard University. It’s quite surreal to find yourself here and it’s also surprising just how accessible the university is to the public. 

Harvard is located in Cambridge which is actually another large city that sits just beside Boston. Luckily, you can easily take the red line on the T a few stops from the center of Boston to the Harvard station and you’ll be just a few feet from campus. Walk through the gates of the county’s most renowned university and imagine what it would have been like to study here should you have been accepted. 

I actually find the campus to be a bit underwhelming; I might be biased since it’s my alma mater, but I think the UCLA campus is much more beautiful. But, the red-brick buildings at the oldest college in the USA does deserve an hour or so walk around. Check out Harvard Yard, the John Harvard statue, Memorial Church, Harvard University Library, Memorial Hall, and Massachusetts Hall. It’s also fun to sit in the quad for a bit and pretend that you are a student. 

Old State House Boston

Boston Common/Freedom Trail

Once you’ve sufficiently meandered around Harvard University’s campus, take the T back to Park Street station on the red line which is the closest stop to Boston Common, America’s oldest public park and the start of the Freedom Trail.

What is the Freedom Trail?

It’s a 2.5 mile tour of the 16 of so of the most prominent sites of the Revolutionary War. More specifically, you’ll pass by meeting houses and churches where important protests were conducted, cemeteries where key figures were buried, and you’ll see exactly where Paul Revere took his midnight ride. Simply follow the red-brick line along the trail which will keep you on the path from Boston Common all the way to Bunker Hill.

You can choose to book a guided tour or a self-guided tour, but it is so important to learn about their significance and not simply stare at these significant historical sights while walking by. The second time I walked the Freedom Trail, I downloaded the Action Tour Guide app which was recommended by the official visitor center, conveniently located in Boston Common right at the start of the Freedom Trail. For $6.99, you can download a self-guided walking tour and walk the trail at your own pace, while still gaining important insight into Boston’s history. 

Just make sure to bring a portable charger with you if you plan on listening to audio on your phone for the majority of the day! Phone battery runs out quickly when you are constantly using Google Maps to navigate, Yelp for lunch recommendations, and taking lots of photos and videos.

Freedom Trail Tours:

Boston: 2.5 Hour Freedom Trail Walking Tour

Freedom Trail: Small Group Tour of Revolutionary Boston (2.5 Hours)

Boston Freedom Trail Walking Tour with Costumed Guide

The Revolutionary Story Walking Tour in Boston

Boston: Freedom Trail Self-Guided Tour

Sam Adams grave

Here are the 16 sites along the Freedom Trail:

  1. Boston Common
  2. Massachusetts State House
  3. Park Street Church
  4. Granary Burial Ground*
  5. King’s Chapel**
  6. Benjamin Franklin Statue
  7. Old Corner Bookstore (yes, sadly this is now a Chipotle)
  8. Old South Meeting House
  9. Old State House
  10. Boston Massacre Site
  11. Faneuil Hall***
  12. Paul Revere House
  13. Old North Church
  14. Copp’s Hill Burial Ground****
  15. USS Constitution
  16. Bunker Hill Monument
Union Oyster House

*The Granary Burial Ground. Take a pint pit stop and head into Beantown Pub which is directly across the street from the cemetery. It’s the only place in the world where you can have a Sam Adams beer while overlooking Sam Adams grave. 

**Directly across from King’s Chapel is the Omni Parker House where you can stop into the small gift shop just past the hotel entrance for an original Boston Cream Pie. 

***Faneuil Hall is one of four buildings in Faneuil Hall Marketplace. The others are Quincey Market, North Market, and South Market which are all indoor/outdoor malls and eateries. Quincey Market in particular is a perfect place to stop for a late afternoon snack. How does a clam chowder bread bowl from Boston Chowda Co sound? Or, you can grab a slice of pizza from Pizzeria Regina. Just don’t get too sick of Italian food, because (spoiler alert) you will end this day in the North End for an incredible Italian feast. 

****Truth be told, I have never actually made it to stops 15 and 16 along the Freedom Trail mainly because I have a herniated disc in my back and the thought of walking across the Charleston Bridge to see the USS Constitution and the Bunker Hill Monument always just seems a tad too far by the time I make it to the North End. Instead, I prefer to walk up to the edge of the Boston Harbor and watch the sunset instead. All this to say, if you don’t make it all the way through the trail, do not feel guilty! 

Modern Pastry cannolis
Modern Pastry

Dinner in North End

The other reason I never make it over into Charlestown is because I always plan on having dinner and cannoli in the North End which is a Boston must. Be sure to make a reservation in advance – unless you are set on going to Giacomo’s Ristorante which does not take them. All of the restaurants in the North End book up quickly, especially on the weekends, so just go on Open Table to read reviews and choose your favorite. 

Native Bostonian and travel companion/tour guide, Caroline, took me for an aperitivo at Caffe Vittoria which is the oldest Italian-style coffee shop in the North End. The vibes are immaculate – imagine a traditional, bustling atmosphere packed with groups of people gossiping excitedly while eating pastries and sipping cappuccinos or a glass of wine. Do keep in mind that it is cash only. 

There is nowhere else to end the night but at Mike’s Pastry or Modern Pastry for cannoli. You might ask, which spot has better? I say, the one with the shortest line. And yes, I have had cannoli from both establishments. Both are absolutely delicious. If you are a cannoli connoisseur, perhaps you might wish to do more research. But, if you have a sweet tooth and love a good pastry, you will undoubtedly fall in love with your cannoli from either Mikes or Modern.

Boston Public Gardens park

Day of Culture: 2 of 2 Days in Boston

You’ve now seen most of the important historical sights in Boston, so let’s spend today getting a better feel for Boston culture. 

Fenway Park/Museum/Duck Tour

Start off strong with a visit to a unique Boston landmark that is of a particular area of interest to you. The choice will vary based on your preferences, but I would suggest either a guided tour of Fenway Park, a visit to one of Boston’s exceptional museums like the Isabella Stewart Gardner Museum, Museum of Fine Arts, or Boston Tea Party Ships & Museum. And, if none of those strike your fancy or if it’s splendid weather in Boston, you can take a Duck Tour along the Charles River.

I’m a sports fan so, for me, the clear choice was to take a tour of the Green Monster and the iconic Fenway Park; it did not disappoint. And while the tour was fabulous, you get bonus points if the Red Sox are playing a game whilst your in Boston, and you attend. However, if you are more into the arts or didn’t get enough of a history lesson yesterday, then one of the museums might be a better fit. Finally, the duck tours -whilst absolutely touristy- provide you with a great excuse to get out on the water and see Boston from a different vantage point. 

Boston Fenway Park: 1-Hour Guided Walking Tour

Tour of Historic Fenway Park, America’s Most Beloved Ballpark

Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

Boston Duck Tour: The Original and World-Famous

Boston Tea Party Ships & Museum Admission

Beacon Hill

After a visit to your Boston attraction of choice, it’s time to head toward glorious Beacon Hill for lunch and a coffee. With its red bricks, black shutters, charming cobblestones, and tree-lined streets, this neighborhood is quintessential Boston and what you might have anticipated Boston to look like prior to your visit. Make sure to wander through some of the streets in the neighborhood, especially Acorn street which is one of the most photographed streets in the world. I would recommend just walking by though because the local residents can get quite aggravated if they spot you taking pictures. 

latte from Tatte bakery

Boston Public Gardens

Is there anywhere better to have lunch than everyone’s favorite Boston bakery, Tatte? I think not! Personally, I am madly in love with their sweet potato and avocado tartine. The bread is soft, the aioli is delicious, the egg is poached perfectly, and the radish and mint garnishes complete each bite to perfection. I purchased the tartine and a vanilla latte to-go from Tatte’s Beacon Hill location and walked a few blocks to the most beautiful place in all of Boston, the Boston Public Gardens. When I say I could come here every day and never tire of its beauty, I truly mean it. Sit yourself on a park bench and watch the goings on and you will be entertained for hours. You’ll spot couples getting married and taking wedding photos, people riding swan boats in the stunning lake, and you might even hear musicians playing live music which will elevate your gardens experience even further. 

sweet potato and avocado tartine from Tatte bakery

Back Bay

Once you’ve spent some quality time in the gardens, slowly make your way across in the direction of the George Washington statue and the Garden of Remembrance 9/11 Memorial. You’ll find yourself in the Back Bay neighborhood of Boston, one of the area’s trendiest spots and what was once a literal bay that was filled in during the 19th century.

There’s much to check out in this prestigious area of Boston. I would suggest starting in the Copley Square, Trinity Church, and Boston Public Library region. From there, zig and zag your way up and down the long blocks on Newbury Street and Commonwealth Ave all the while making your way toward the Charles River Esplanade for sunset. Get your shopping on at Newbury Street and gawk at the beautiful Victorian brownstones along Commonwealth Ave. 

Charles River Esplanade at sunset

Charles River Esplanade

End your second day in Boston walking along the Charles River Esplanade at sunset. If the weather is nice, you’ll find native Bostonians picnicking and students from the local colleges’ sailing teams out on the river practicing their sport. We found a beautiful spot with an unobstructed view of the sunset before making our way to a local beer garden popup – the Owl’s Nest – that is in the area during the summer season. Grab dinner in the Back Bay at Saltie Girl or any of the other restaurants that strike your fancy where you can dine al fresco (weather permitting). And, if you’re looking to have drinks for your final evening in Boston, I’d suggest checking out an area of the city that you have yet to explore.  

Have you been to Boston before? When is your favorite time of year to visit? And, what activity are you most looking forward to during your 2 days in Boston? Let us know in the comments below!

Don’t forget to check out these other posts on WOAW!

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Winter Packing List: What to Wear in New York City

What Shoes to Wear in New York Winter

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