While Boston is a large city with plenty to do and see for a longer trip, it is also possible to get a lot done even if you just have one day to spare. This itinerary is perfect if you are visiting in the summer when the weather is clear as it involves plenty of walking or biking and is generally out of doors. Boston is a city filled with so much American history and sites to discover and learn about. The energy of it’s revolutionary past really does still course through the soul of the city and you can feel it pulse through the cobblestone roads with each and every step.
To start the day, a quick coffee and pastry should be acquired to fuel the long, sight seeing hours ahead. My suggestion would be to stop at Flour Bakery, which has three locations throughout the city. The coffee is handled with care and is truly high quality. Plus the pastry options are endless and all are extremely appealing. My suggestion would be for the indescribably amazing sticky bun. They make them fresh every day and they sell them until they run out. They are quite large but totally worth it especially with a walking tour on the agenda. If you want a full breakfast/brunch experience, I would recommend Lulu’s Allston, which offers truly innovative and exciting dishes like White Trash Hash, Short Rib Mac & Cheese, and Croissant French Toast!
The best thing about Boston is that they offer a self guided walking tour called the Freedom Trail. It is a 2.5-mile long trail that is literally marked throughout the city by a red line. Start by wandering the beautiful Boston Common Park, which is a must see in the city, and then picking up the trail from there. It will take you past all the great historic sites like the Boston Massacre site, Old South meeting House, Paul Revere House, Old North Church, and ending at Bunker Hill. It also offers small signs that give you a bit of the history of each landmark. If you are looking to move around quicker, I would definitely suggest renting a bike as it is a good way to speed up the tour when you have limited time to spare.
Next, You should either bike, walk, or cab over to Cambridge from Bunker Hill. Take a stroll through Harvard Yard. The campus is truly spectacular offering plentiful open spaces and wonderful architecture. The town of Cambridge boasts tons of small shops, boutiques, and bookstores to wander in and out of. If all that walking or biking has made you hungry, stop at Beat Brasserie for a cool, jazzy, and psychedelic lunch with live music or Clover if you prefer more of a café style food experience.
After re-fueling, head back across the river and take a stroll along the Boston Harbor. If you are into slightly dorky historical experiences, I would recommend visiting the Boston Tea Party Ships and Museum. There are actors that take you through the historical events leading up to and including the Boston Tea Party. You even get to throw some fake tea boxes into the Harbor. This is particularly fun if you have kids with you! Next, be sure to check out Faneuil Hall Marketplace and Quincy Market as well which has been around since 1742 and offers about 150 shops and restaurants. As well, there will usually be street performers or live music around the promenade to just sit, watch and relax after a long day of sightseeing. As well this can be perfect spot to grab something for dinner. You can find some restaurants there that offer true New England style meals like clam chowder and fish based meals.
You can also consider checking out a baseball game at Fenway Park if you are a sports lover. The games do tend to sell out, however, so if this is something you would love to do, definitely try to book it in advance. If you have some time at night you can stop by the Improv Asylum for a comedy show, go the Skywalk Observatory to take in the nighttime views of Boston from above, or check out Shakespeare on the Common if there happens to be a show that night! As well, Boston is known for its pubs and beer so you can stop by basically any bar and pick up a nice glass of craft beer or even just a Samuel Adams!
There are plenty of other options available in Boston to make an extended stay 100% worth it, but if you are limited to just a day, the best way to get to know the city is just through walking or biking around. You can get a true sense of the history and culture that permeate throughout every street. This is the city that started the American Revolution and that defiant and passionate energy is absolutely still alive today. You only have to get out there and start walking to just see for yourself!