My favorite big city in the U.S. is Boston. Steeped in history and packed with charm, Boston is a fantastic destination for travelers who love culture, walkable neighborhoods, and great food. Whether it’s your first visit or a return trip, the city offers plenty to see and do. I’ve been three times now and each time I find something new to see and do or a new street to wander down and take in.
Walk the Freedom Trail
The Freedom Trail is one of the best ways to experience Boston’s history. Don’t miss this, it really helps tell the story of Boston and U.S. history. This well-marked path takes you past major landmarks like the Paul Revere House ($6 for adults), Old North Church (starts at $10 for adults), and Bunker Hill Monument. It’s an easy walk and a rewarding introduction to the city. Best of all, it’s free unless you want to go to certain locations.
Relax in Boston’s Best Green Spaces
My favorite spot in the city is the Boston Public Garden. Located downtown, it’s perfect for a stroll and offers beautiful city views. Skip the picnic, though as the squirrels are bold (one actually climbed my leg while I was stopped and stood checking my phone.) And whatever you do, don’t feed them. Don’t miss the famous duckling statues.
Right next door is Boston Common, the oldest public park in the U.S. In winter, the Frog Pond turns into an ice-skating rink, though when I was there it seemed a little slushy (They’d gotten a bit of rain.)
Explore Beacon Hill & Historic Sites
Nearby, the Granary Burial Ground is worth a visit. It’s the final resting place of Samuel Adams and other notable figures.
While the Cheers baris close by, I prefer wandering through Beacon Hill.
See Cheers if you’re into that, but I thought it was a bit too touristy and crowded for my liking. Acorn Street may be crowded, but the entire neighborhood is charming.
Don’t Miss the USS Constitution aka Old Ironsides
One of the places that I very much enjoyed was visiting the USS Constitution and Museum. (Free). The cannon is fired daily in the morning and crews still work on the ship. It’s a fascinating look into naval history, especially a vessel that played such a major role in the War of 1812. Allow at least an hour here.
Visit the Boston Public Library
The Boston Public Library is a must-see, even if you’re not a library person. The architecture is stunning, and the interior courtyard is a peaceful escape from the city. The library is absolutely stunning. There’s also a nice cafe there. Next time I go, I’m spending time in the Map Room Tea Lounge.
Museums & the Waterfront
Boston has excellent museums, including the Museum of Fine Arts Boston (adults $30) and the Isabella Stewart Gardner Museum (adults $25). That said, one of the city’s greatest pleasures is simply wandering, especially along the harbor and waterfront paths.
Hop Over to Cambridge
Cambridge, home to Harvard, is worth exploring. Harvard has some museums, and you can do a guided tour if you want, but I very much just enjoyed strolling around campus looking at all the old buildings.
Shop, Eat, and Wander
For shopping and people-watching, stroll along Newbury Street, which is great for browsing boutiques and grabbing coffee.
Food lovers shouldn’t miss the North End. Its narrow streets are lined with Italian restaurants, bakeries, and cafés which is perfect for a long meal and dessert.
And leave time here for just taking in the sites. While on a visit, we stumbled upon an outdoor street festival celebrating the Bruins. I wish we would have come across it sooner, but there were activities, games, entertainment and more.
Where To Stay in Boston
There are plenty of great hotel options. I’ve stayed near Boston Common and more recently in the Seaport District Boston. I especially enjoyed the Omni Boston at the Seaport Hotel, thanks to its modern feel, nearby restaurants, and quick access to the airport. The Boston Common area has more of an edge because it’s a bit closer to attractions, but there, Back Bay, Seaport, etc., are all very walkable to the majority of things you might want to see in Boston.
Quick Planning Tips
- Grab coffee or breakfast at Tatte Bakery
- Walk part of the Boston Harborwalk
- Expect crowds at peak tourist spots—but quieter neighborhoods are always nearby
- No need for a car. Most attractions are walkable and parking is hard to find and expensive.
- Take a ride share to/from the airport. It’s fairly quick to get into town from the airport.
There are many other activities in Bean Town including Duck Boat rides, Harbor Cruises, etc. But honestly, I just like the vibe of the city, the wandering through the old neighborhoods and admiring the architecture. It’s a city that I enjoy and one in which if circumstances were different, I’d probably live there. What do you think, have you been to Boston? What’s you’re favorite thing to do there?
