Boston is a city that deserves at least five days for a visit. If you want to do a day trip to Cape Cod or the North Shore, you may want to add a few more days. Yet, I come across people who say they are only in Boston for 24 or 48 hours, or even a long weekend of 72 hours. And those visitors ask me: what are the things that are must-see in the city? Many of these individuals spending limited time here may never have visited before, either.
This blog post will cover things you should do if you’ve never been to the city and want a good overview of what Boston is about. This is through the lens of what I see as important, so your opinions may vary. Yet, I’ve spoken to hundreds if not thousands of visitors to Boston in the past five years, so I’m also taking into account what I’ve heard from them. I also want to throw in some hidden gems that many guests miss.
Start off with a trolley tour from Old Town Trolleys. There are a few ways to get a broad overview of the city. But I prefer Old Town Trolley because they cover a wider area, including going to the Seaport neighborhood and MIT in Cambridge. Your ticket also gets discounts at the Old State House and the Tea Party Museum, which are both worth hitting up. They’re also both on the trolley tour route. On your tour the driver will give you an overview of what you’re seeing, some history, and fun facts. Ride the entire route and then ride the trolley back to anyplace you want to visit again. All tickets are good for two days’ worth of rides, which makes this tour an even better deal.
For lunch hit up Boston’s North End, also known as our Little Italy (but only call it that if you want to out yourself as a tourist). There are more than 80 restaurants in this less than one square mile neighborhood. Most are open for lunch and offer specials. They’re also not as crowded then. Almost all the restaurants are solid choices, but check out my recommendations for some favorites.
In the afternoon, hop back on the trolley and go to Bunker Hill Monument. From there you can walk The Freedom Trail. This 2.5-mile brick path covers over a dozen historical sites that are important in our nation’s history. Feel free to take your time and go into the sites that interest you, or walk the trail and you’ll finish the route in as quick as 90 minutes. Don’t forget to check out some of the odds and ends on the Trail, which will add a little liveliness to this historic path.
If you have some time, check out the Boston Public Garden, located next to the Boston Common. (The Common is the oldest public park in the United States. The Public Garden is the oldest public garden in the US. We’re a city that’s big on history if you haven’t figured that out yet.) See the Make Way For Ducklings statues or rent a swan boat and paddle around the pond. Afterward, for dinner, make your way down the shopping-centric Newbury Street and see which restaurants suit your fancy. Along the way you can check out stores that range from Tiffany and Co. to Urban Outfitters.
Another option is to head to Charles Street on Beacon Hill. There you’ll find many boutique shops as well as plenty of food options. Afterward, walk around Boston’s richest (and one of the oldest) neighborhood. Make sure and see Louisburg Square and Acorn Street.
In the evening, head to the Theatre District to catch a show or head down to the Esplanade and stroll along the Charles River.
Grab breakfast at Friendly Toast, a diner in Back Bay (make sure to get there early), or Mike & Patty’s in Bay Village. The latter is a hole in the wall whose breakfast sandwiches are top notch. The former is a fun diner with a huge menu.
Today is a great day for a picnic, but not at any old location. How about having it at a 19th-century fort on an island in Boston Harbor? Grab some picnic foods and head to Long Wharf to board a ferry for Georges Island. Enjoy the breeze off the water and your lunch. Then explore Fort Warren and take a guided tour by a National Park Service Ranger. Make sure and bring a bag to carry back your trash, as all the islands are carry on, carry off with garbage.
Spend your afternoon hitting up some of the locations you may have missed on the Trolley Tour the day before. I can't recommend the Mapparium enough. It’s a 30-foot-tall stained-glass globe which you can walk into that depicts the world as it was in 1935. Afterward, head over to the Christian Science Church for a free tour and see the beautiful stained glass and architecture.
Walk down Huntington Avenue to the Boston Public Library and explore this wonderful building (both the old part and the modern one). If it’s possible, take the free tour to learn more about the art and architecture.
For dinner, check out Chinatown. If you’re vegetarian, I recommend My Thai Vegan Café, but in Chinatown you’ll find everything from dumplings to hot pot.
End the day with a drink at either Yvonne’s or The Last Hurrah (located in the Omni Parker House). Both are fine cocktail bars with class.
Today is the day to hop on the T, which is what Bostonians call our subway system. Buy a day pass from a kiosk at any subway station and take the Orange Line to the end at Forest Hills. If you're in town on a weekend, get brunch at The Dogwood, located right next to the station.
There are two things worth checking out in this immediate area: Arnold Arboretum and Forest Hills Cemetery. The Arboretum is a partnership between Harvard University and the city of Boston. It’s the oldest public arboretum in North America. At 281 acres it’s got a creek, hills with great views, a Colonial cemetery, and a bonsai garden. After that, check out Forest Hills Cemetery, located on the other side of the T station. Here you’ll find great sculptures, beautiful grounds, grand mausoleums, and the final resting place of a litany of famous people. It’s one of my favorite places to visit because of its mix of old and new, as well as how peaceful and beautiful it is.
Head back to the Forest Hills T station and walk up South Street (which will merge into Centre Street after a while). You’re in the Jamaica Plain neighborhood, a hip but quaint residential part of Boston. As you walk up Centre Street you’ll find a bevy of cute shops and restaurants. Try one of them out for lunch. And then head to either JP Licks or FoMu for some ice cream!
Next, hop on the Route 39 bus and take it to the stop for the Museum of Fine Arts. While I do recommend a trip to the MFA, if you’re here for a limited time I actually prefer the nearby Isabella Stewart Gardner Museum. This building is a mixture of early 20th-century mansion and art gallery, with a beautiful courtyard to boot. You’ll find art from Ancient Greece up through the late 19th-century. This was also the site of the largest art heist in history: $500 million worth of items in 1990. The art is still missing and the crime remains unsolved.
From the Gardner head over to Fenway Park and get a tour of the stadium. I’m not much of a sports fan, but even I enjoyed my tour of the oldest professional baseball stadium in America. There’s some great history here and the tour allows you to go behind the scenes. There’s also a museum at the end of the tour. Boston is a sports town and it’s good to get a feel for that on your visit.
Many visitors come to Boston with an intention to eat seafood, especially lobster. And we’ve got more than enough places to please. Any of the following should meet your craving: Neptune Oyster, Sail Loft, James Hook, and of course any Legal Seafood location is a safe bet. In the evening head over to one of the best bars in the North End for a drink.
And most importantly, make sure you squeeze in a tour with Historic Boston Crime Tours!