Discover Boston Like a Local: The Complete Guide to 3 Awesome Days in Boston
Welcome to Boston! Today I’m taking you on a local’s tour of Boston. From where to stay, where to eat, and my favorite things to do. How do I know? I’ve lived here nearly my entire life, from childhood and to adulthood.
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Boston, known as “Beantown” and “the Hub" is a welcoming city brimming with history, culture, innovation, and natural beauty. You can explore landmarks like the Freedom Trail, where you can walk in the steps of the founding fathers, or the beloved Fenway Park, a must-visit for any baseball fan.
Boston is a city of neighborhoods, each with its unique charm. Take a stroll in the Back Bay area, home to Victorian brownstone houses, chic boutiques, and trendy cafes. Or soak up the creative atmosphere of the SoWa Art & Design District, brimming with art galleries, boutique shops, and the popular SoWa Open Market. Each Boston neighborhood has its distinct personality, so you can always find what you’re looking for.
Neighborhoods
The Back Bay
The Back Bay is a fashionable neighborhood that is an absolute must-see! It's conveniently nestled near the Charles River and Fenway Park, making it an ideal starting point for your Boston adventure. The Back Bay is known for picturesque Victorian brownstones and a bustling shopping scene. Stroll down Newbury Street and Boylston Street for shopping or relaxing in one of the city’s trendy cafes. Pop into the Boston Public Library, the first large free municipal library in the country. Or take a ride in the Swan Boats in the beautiful Boston Public Garden.
The South End
The South End is another must-visit neighborhood that offers a unique blend of historic charm and modern convenience. Located just south of Back Bay, it's known for its elegant row houses, vibrant arts scene, and some of the best restaurants in the city. You can explore the neighborhood's many art galleries and studios, especially during the monthly SoWa Art Walks. The SoWa Open Market is a favorite weekend destination, featuring local artisans, food trucks, and a farmer's market.
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Beacon Hill
Beacon Hill, located just north of Boston Common, is a historic and picturesque neighborhood. It’s a close call whether the North End or Beacon Hill is my favorite neighborhood, but Beacon Hill juuuust edges out the North End. What really gets me are the gas-lit streets and federal-style rowhouses. You can explore the Massachusetts State House, with its iconic golden dome, or stroll down the brick sidewalks of Acorn Street, often called the most photographed street in the US (for good reason). The neighborhood is also home to charming boutiques and antique shops, along Charles Street, along with the best bookstore ever, Beacon Hill Books and Cafe.
The North End
The North End, Boston's oldest residential community, is a charming neighborhood steeped in history and bursting with restaurants. Nestled between the Charles River and the Rose Kennedy Greenway, this neighborhood is renowned for its cobblestone streets, historic sights, and Italian restaurants. You can visit Paul Revere's House and the Old North Church. Walk down Hanover Street for some of the best restaurants in the city. The North End is definitely where you want to get some of the best seafood in Boston. No trip to the North End is complete without a stop at either Mike’s Pastry or Modern Pastry.
Chinatown
Chinatown, located in the heart of downtown Boston, is a vibrant and bustling neighborhood that offers a unique blend of cultural experiences. Here, you'll find an array of authentic Asian cuisine, traditional bakeries, and specialty grocery stores lining its narrow streets. The neighborhood is also home to the Chinatown Gate, a beautiful, traditional Chinese gate that marks the entrance to Chinatown.
Seaport
Seaport, located on the Boston Harbor, is Boston's newest neighborhood. The Seaport is convenient for travelers and full of modern conveniences, with hotels, restaurants, and shops spread across the neighborhood. While the Seaport is a convenient place to base a visit to Boston, it lacks the history and charm you’ll find in the rest of the Boston neighborhoods.
Where to STAY
Like I said above, the Seaport is full of hotels and restaurants, making it a convenient base.
A few of my favorite hotels in the Seaport:
The Envoy: The Envoy is conveniently located next to the bridge leading to downtown. It also has the best roof deck in Boston.
The Westin Seaport: You can really never go wrong staying in a Westin. The Westin is attached to the Boston Convention Center.
Omni at Seaport: Bright, spacious rooms. The hotel has an outdoor swimming pool and is across the street from the Boston Convention Center.
If you’re looking for something more centrally located, the Back Bay is a great choice.
A few of my favorite hotels in the Back Bay:
Fairmont Copley: For an upscale visit in a prime location.
Four Seasons: Impeccable hotel overlooking the Public Gardens.
Mandarin Oriental: For when you want to treat yourself.
HOW To Get Around
Please, please, please don’t drive. Traffic is a nightmare just all of the time now. And our streets were originally horse paths, and it shows. Streets turn into one-ways without notice and if you’re ever able to get to the top of Beacon Hill, you’ll never find your way back down. Luckily, Boston manages to pack a lot into a fairly small space and most of the city is walkable. We also have Bluebikes, a bike-share program. You pay by the hour and there are stations to get and return a bike all over Boston, Cambridge, Somerville, Newton, and Brookline.
Or, we have the “T,” as we call the MBTA. Ok, if you’ve googled the T you’ll see it’s fraught with issues, but it’s still better than driving. You can get to most parts of Boston on one of the color-coded lines. The Red Line runs from Braintree to Cambridge and cuts through South Boston to South Station and up Tremont Street. The Orange Line runs from Jamaica Plain to Melrose and stops in Back Bay, Chinatown, Haymarket (just across the street from the North End), and North Station (attached to the Garden, home to the Bruins and Celtics). The Blue Line is the shortest line, running from downtown to East Boston with stops at Government Center, the Aquarium, and Logan Airport. The Green Line is really 4 lines in one - the B Line runs out to Boston College, the C Line runs out to Cleveland Circle, the D Line runs out to Newton, and the E Line runs out to Jamaica Plain.
WHERE You Should Eat
Seafood
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The Daily Catch: Like most restaurants in the North End it’s small, only about 20 tables. And they only take cash. But it’s well worth the trouble of stopping at an ATM, they have some of the best seafood dishes I’ve ever tasted.
Prezza: Get the Fish Stew. Trust me.
B&G Oysters: It’s in the South End, not the North End but it still deserves to make the list.
Union Oyster House: Also not in the North End, but they have the best clam chowder in Boston and you have to try clam chowder when you’re in Boston.
Outdoor Dining
The Envoy Hotel: The Envoy in the Seaport has the best roof deck in Boston. They have comfortable chairs and couches around low tables for lounge areas or high-top tables if you want to eat a meal.
Legal Harborside: One of Legal Seafood’s locations, this one right on the water in the Seaport.
Bartaco: Another one in the Seaport. Bartaco has a patio, not a roof deck, but it’s an amazing patio. Plus they have the best tacos.
Coffee Shops, Cafes, and Diners
Dunkins: of course, you have to try Dunkins while you’re in Boston. Order a Regular and you’ll get equal parts sugar and cream and coffee. But somehow it’s still delicious.
Cafe Nero: This is actually one of the best coffee shops in Boston. You can find them all over the city.
Pavement Coffee: A local coffee shop that you can find throughout the city.
South Street Diner: An old-fashioned diner.
JP Licks: This is an ice cream place, and they have delicious ice cream, but they also have amazing coffee.
Other favorite restaurants
Tres Gatos: The best tapas in Boston, located in the Jamaica Plain neighborhood.
Aquitaine: A French bistro in the South End with an amazing dinner and brunch menu.
Regina Pizzeria: The best pizza in Boston.
Belle Island Seafood: Just outside Boston in Winthrop, but it’s worth the ride for the best Lobster Rolls, ever.
WHAT To Do In Boston
There’s something for everyone in Boston, from sports events to museums to shopping.
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Sports
There’s never a time in Boston when one of the big 4 teams (Red Sox, Celtics, Bruins, and Patriots) isn’t playing. If you catch a Red Sox game you’ll have the benefit of visiting the famed Fenway Park. If you catch the Celtics or Bruins you’ll get to visit the Garden, which has gone major expansions and renovations. If you catch the Patriots you’ll get to visit Patriots Place, which is the neighborhood the Patriots built around Gillette Stadium down in Foxboro.
Museums
Interested in art museums? Boston is the home to the Museum of Fine Arts and the Isabella Stewart Gardner Museum. More interested in science? Boston is home to the Science Museum. Interested in history? Boston has the JFK Library, the Boston Tea Party Ships and Museum, and the USS Constitution Museum.
History
Boston is the birthplace of the American Revolution. You can walk the Freedom Trail to follow in our forefathers’ footsteps. You’ll see the Olde North Church and the Paul Revere House in the North End. You can stop at the Green Dragon for a quick drink to see where the idea of the Tea Party was dreamed up (over a couple of drinks, of course). You can take a day trip out to Concord and Lexington to see some of the first battlefields. You can visit the Old State House, which was a meeting place and the center of politics pre-Revolutionary War.
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Parks
Boston has some great outdoor spaces. You can run or bike along the Charles. Or you can rent a sailboat or a paddle board for the day or even a few hours. If you want to stick along the Esplanade, you can catch an outdoor concert or movie at the Hatch Shell and grab dinner at one of the food trucks. Or you can walk through America’s oldest park, the Boston Common. During the summer you’ll find food trucks and pop-up stalls and in the winter you can skate on the Frog Pond. Just across the street is the Public Gardens, my favorite park. When you walk through you might see a wedding happening in one of the corners.
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Boston Public Library
Even if you aren’t a bibliophile the central branch of the Boston Public Library is worth a visit. You can stop for afternoon tea at the Tea Room or sit in the courtyard, a favorite spot for weddings at BPL.
Day Trips
Salem
Salem is about a 30-minute train ride or a 45-60 minute drive from Boston. Just be careful in October, it can get crowded!
Cape Cod
In the summer the MBTA runs the Cape Flyer, which is the only time the train runs all the way to the Cape. Otherwise, you can take the bus or drive.
Concord/Lexington
Best to drive out to Concord or Lexington, since public transportation isn’t readily available out there. As long as you avoid rush hour, it’s only about a 20-minute drive.
HELPFUL Tips and Fun Facts
Best times to visit
Although the last few years haven’t been bad, Boston winters can be brutal. The best times to visit are May, June, September, and October. You’ll miss the worst of the summer crowds and have the best weather.
Watch the sidewalks
Especially when you’re downtown you’ll be sharing the sidewalks with Bostonians going to and from work and they are in a rush. You’re likely moving a little slower, so keep to the side and don’t let your entire party spread across the entire sidewalk so no one can get by you.
We’re nice!
We aren’t terribly patient or outgoing but we are nice! Especially if you need directions somewhere, don’t be afraid to ask!
I hope you enjoyed this local’s guide to Boston!
