You don’t have to plan a long trip to cover a lot of ground. While I’m sure most of us would love to have week-long - if not longer - trips to any destination we visit, it’s not always an option. I love long trips, I love having extra time to explore - but short trips have this special quality to them. You know there’s only a few days to pack in as much as possible and it gives you a certain high from the anticipation. Almost like a Christmas morning feel. It’s a day that comes once a year and because of that, it’s extra special. To cover as much ground as possible, here are our recommendations for three days in Boston.
WHERE TO STAY
When your time is limited in any given destination, you want to pick as central of a location as you can. We recommend finding a place in the North End, Back Bay or Beacon Hill neighborhoods or somewhere within that general area. The Boxer Boston, located in the West End, is walking distance from the North End and Beacon Hill which is connected to the Back Bay. There is a major public transportation hub within steps of the hotel making it even easier to access other parts of the city. It served as a great central point for my own travel goals.
DAY 1: Freedom Trail + All Things History
Start with breakfast at Thinking Cup while you map your best route, take yourself through all of the Freedom Trail stops at the North end choose one or two spots to venture inside. Don’t think you’re interested in history? Still follow the Freedom Trail. It has sixteen sites, many of which are probably on your list anyway. It’s also one of the most comprehensive “tours” of Boston you’ll get. It takes you through the North End and Beacon Hill as well as parts of the Downtown, Faneuil Hall, Haymarket and Charlestown. Spots you’ll hit include the Boston Common, Bunker Hill Monument, USS Constitution, Paul Revere House, Charles Street in Beacon Hill and more.
Go Off Trail
While tackling the Freedom Trail, mark the sites which you are the MOST interested in. It is a hike so if there are parts that don’t interest you as much, you can walk by without taking an extra breath. This will also give you the chance to hit sites that are not included on the Freedom Trail but near it. For example, Acorn Street in Beacon Hill is within a block of three Freedom Trail stops. Mike’s Pastry and several other great food places are along the route that passes through North End. The Freedom Trail route will cover any of the historical sites you’re interested in and take you by other sites that you can cover in quick stops. More importantly, it’s FREE! Grab a guide for yourself and self-instruct your own route.
Grab Some Sicilian-Style Grub
Let’s pretend you start in Beacon Hill on your Freedom Tour. Start the day with breakfast at Tatte Bakery + Cafe. Make your way through Beacon Hill, around the Government center, through Haymarket and over to the North End. Grab a slice of Sicilian-style pizza at Galleria Umberto (cash-only) before picking up a cannoli or two at Mike’s Pastry. When you get back, enjoy a casual dinner at Finch because man, do they have good burgers!
DAY 2: Boston Common + Back Bay - Stay Local
Head back over to the Boston Common on day two. The Freedom Trail will only have had you glaze the park edges and this is something you don’t want to miss. Boston Common is like Central Park in NYC or Millennium Park in Chicago. The Common is America’s oldest park and a whopping 50 acres with gorgeous landscaping, statues and memorials, kiddie parks, frog ponds, live entertainment and more. Walk along Beacon Street to get a photo at the Cheers Restaurant which is just outside of the Back Bay neighborhood. Their menu is pretty basic American pub-fare if that’s something you’re interested in for lunch. If not, keep walking southeast towards the Back Bay neighborhood for more options.
Indulge Your Inner Rory Gilmore + Hit Up Some Latin Cuisine
Back Bay is home to the Boston Public Library and Mapparium, one of the most underrated sites to visit in Boston. The 3-story, stained-glass globe has a 30-foot long bridge to explore in detail. It’s a masterpiece and one-of-a-kind experience. Admission is only $6 for adults making it an inexpensive stop on your three day visit. Once you’ve successfully been overwhelmed by the Mapparium, head to the Boston Public Library. Bates Hall has a barrel-arched ceiling, purely magnificent in its design. See several murals, browse thousands of books and take a moment for yourself in the courtyard.
Still have some time before dinner? Get some shopping done along Newbury Street before grabbing a bite at Masa. A local favorite, the restaurant serves up Southwest, Spanish and Mexican cuisine. Don’t get too full though because you’ll want to head over to South End for a visit to Beehive before going back to your hotel. Boston’s most popular Bohemian bar, they host live music every day and are considered one of the “Top 100 Jazz Clubs in the World.”
DAY 3: Explore Outside of Boston
No trip to Boston should be complete without a half-day trip to Cambridge. Rise early for a quick ride over to Harvard Square. Grab a bite to eat at Crema Co. before strolling through the Harvard Yard. If you have time and it’s open, head to the Longfellow House-Washington’s National Headquarters for a tour. If it's not open or you're not interested, consider browsing one of the Harvard museums. Take one more walk around Harvard Square before heading back to the city.
Explore Something Unplanned
Walk along the Charles River to get a taste of the Esplanade or head back to Faneuil Hall to people watch. My favorite part of travel is wandering without a goal. Use your final afternoon to enjoy an area you’d like to return to. Walk the city as if you’re a local and take in all the beauty it has to offer. You’ve packed quite a few things into the last two and a half days so take a little time for yourself.
Once you’ve successfully been lost a few times and happened upon a few gems, head back to the North End. Get a pizza dinner at Locale or classic Italian at La Galleria 33. You’ll leave the city satisfied and feeling accomplished because you packed a lot of fantastic sites into three short days. Go ahead, have that second glass of wine. Get a dessert you normally would refrain from. You deserve it. And now that you’ve had a chance to get a taste of Boston, you can write your list of everything you’d like to see when you come back. You know it’s inevitable.