The City Guide Boston gives you an in-depth look at one of the oldest cities in America.

Ever since I moved back to Boston in June, I’ve been eager to reacquaint myself with my home and do some backyard travel. For a city that used to be so familiar, everything has become fantastically unfamiliar and I find myself relearning all things I once knew by heart. I’m lucky to have been given a second chance at getting to know my hometown in this City Guide Boston. Boston is the capital of Massachusetts, the 6th state in the USA. Located on the eastern seaboard, it is only a 4-hour drive from New York City. Every corner of Boston is laden with history and even though the United States is relatively young compared to every other country in the world, there’s something about Boston that feels rather nostalgic and sentimental. It’s a city of firsts, instilling in every Bostonian a sense of unrivaled pride for all the accolades present in one city: the first metro in the continent, the first public park in the USA, the first university in the Americas… we even have the oldest running restaurant in the country! Whether by land or by sea, helicopter or your own two feet, Boston is begging to be explored. I highly recommend you read up on different Tourist Passes to get the most bang for your buck for when you visit.

✱ FANEUIL HALL MARKETPLACE

Wander around the marketplace, one of four locations in the complex of 100 shops and restaurants set within the colonial-era buildings and visited by 18,000,000 people. During summertime, outdoor performers flood the promenade with their juggling, magic, and acrobatic acts.

✱ FENWAY PARK

Catch America’s favorite pastime at the country’s oldest major league baseball stadium and home of the Red Sox.

✱ THE FREEDOM TRAIL

Follow the red brick road, a2.5-mile self-guided tour of Boston’s historic sites leading you to the likes of Old North Church, Paul Revere’s house, and the USS Constitution.

✱ THE NORTH END

Appreciate Boston’s immigrant communities in places like , Boston’s Italian enclave where pastry rivals Mike Pastry’s and Modern Pastry battle it out for the best cannoli (a Sicilian dessert).

✱ ISABELLA STEWART GARDNER MUSEUM

For art museum mavens, ogling the one-of-a-kind collection of in her private Venetian atrium is a must. It’s free admission on your birthday and if your name is Isabella, congrats! You’ve won free entry for life! The empty frames on the wall used to be the home of pieces that were stolen in the world’s most expensive art heist back in 1990.

Fun Fact: If your name is Isabella, you get into the museum for free!

✱ NEWBURY STREET

The brownstone-lined street in upper crust Back Bay is a congregation of high-end designer boutiques, as well as fast fashion names like H&M and Urban Outfitters. PS, Clothes are tax-free in Massachusetts.

✱ PRUDENTIAL CENTER

Survey the city from new heights atop the Prudential Center’s Skywalk Observatory on the 50th Floor. Kill two birds with one stone by going one floor up to visit the ritzy Top of the Hub restaurant, featuring cocktail lounge seats that offer the same view, plus a drink in hand.

✱ CHARLES RIVER

… Continuing on with fresh perspectives, rent a kayak and paddle down the Charles, swerving through sailboats, to get the best view of the Boston skyline.

✱ ACORN STREET

Walk down Boston’s most photographed street, a narrow cobblestone alleyway lined with gas lamps and rowhouses from the 1800s.

Pro Tip: Beat the crowds on weekdays in the late afternoon. Or better yet, come during Christmas when all the brownstones are decked in their finest holiday array.

✱ HARVARD SQUARE

In September, thousands of collegiates flock to the academic hub of the United States. Visit the hallowed grounds of America’s oldest higher education institution, Harvard University, with MIT just a few stops down the Red Line on Massachusetts Ave.

✱ BOSTON COMMONS AND THE PUBLIC GARDEN

Visiting in winter? Glide across Frog Pond Skating Rink set in Boston Commons, the oldest public park in the United States. Right across the street is the Boston Public Gardens, best enjoyed in the summertime, when fleets of swan boats can be seen drifting across  the pond and the garden is in full bloom.

IF YOU WANT TO TRY REAL BOSTON SEAFOOD

Eating seafood is about as New England as it gets. In Boston, you have plenty of options, almost too many, so here’s the general breakdown:

• JAMES HOOK & CO. has been loading up their lobster rolls since 1925. (15-17 Northern Ave, Boston, MA 02110)
• NEPTUNE OYSTER is also in the running for Boston’s best lobster roll. (63 Salem St # 1, Boston, MA 02113)
• THE BARKING CRAB is an open-air dining establishment right on the waterfront. The space is famous on the tourist track, but the food has been waning in quality. (88 Sleeper St, Boston, MA 02210)
• LEGAL HARBORSIDE by popular vote, wins Best Clam Chowder ( known by locals as “chowdah.”) Endorsed by Ronald Reagan, the Legal recipe is served at every presidential inauguration and can be found at Fenway Park too. (270 Northern Ave, Boston, MA 02210)
• UNION OYSTER HOUSE is the place slurp up some of that Boston brine from freshly shucked oysters and it also holds the title for the oldest restaurant in the USA in continuous operation. (41 Union St, Boston, MA 02108)

IF YOU WANT TO SAMPLE THE BEST ITALIAN FOOD THIS SIDE OF ROME

• GIACOMO’S – The people come en masse to this one room, family-operated trattoria right on the main drag of The North End. Expect a line, no matter how early you get there, with an average wait time of 2 hours on a sunny day. The standouts on this Italian menu are the Butternut Ravioli and the Linguini with a Fra-Como sauce (a hybrid of the house marinara, the Giacomo, and the fra diavolo, a spicy marinara.) If you can’t stomach the wait, there is a second restaurant in South End that accepts reservations, is much quieter and larger, but lacks the ambiance of the flagship. Cash only. (355 Hanover St, Boston, MA 02113)

IF YOU LIKE FOOD HALLS

• BOSTON PUBLIC MARKET –  The indoor food hallin downtown Boston showcases around 40 vendors selling the freshest bounty that is all locally sourced (each stall proudly display where all their ingredients come from). With a mission to educate and nourish the community, you can also take cooking lessons at The Kitchen, an on-site cooking studio. My top picks: Red’s Best (seafood), Red Apple Farm (for hot apple cider), Inna’s Kitchen (Israeli food), and Crescent Ridge (ice cream). (100 Hanover St, Boston, MA 02108)
• TIME OUT MARKET BOSTON – The newest addition to the Boston food scene, opened in 2019, is only a stone’s throw away from the famous Fenway ballpark. Opened by one of my favorite media companies, Time Out, this food hall is latest in the string of Time Out Markets cropping up in major cities around the world. There’s a ton of seating, making the food hall big group friendly. Standouts include the crispy Nori sushi tacos at Gogo ya, The Cajun karaage chicken sando at Ms. Cluck’s Deluxe Chicken & Dumplings, and The Nova Lox Sandwich at Mameleh’s, and The Cragie Burger at Craigie Burger. There are also a number of bars housed inside this swanky hall. The howcases around 40 vendors selling the freshest bounty that is all locally sourced (each stall identifies where all their ingredients come from. (401 Park Dr, Boston, MA 02215)

My sister was featured in the Time Out Market Boston promo video! Check it out below:

• ROXY’S GRILLED CHEESE – Once a food truck, the Roxy’s Grilled Cheese enterprise grew so big that it is now a brick-and-mortar shop. Today, the city’s most famous grilled cheese purveyors flip and sizzle gourmet grilled cheeses and you can order them also gluten-free and/or vegan! Just don’t forget the truffle fries. At the Cambridge location, a “barcade” for pinball wizards who can hold their drink is hidden behind the seemingly innocent swinging kitchen double doors. After the double doors, you’ll see a refrigerator door leading up to the secret A4CADE. Race your buddies on the coin-operated driving simulators and drink mystery slushies out of R2D2 cups. (292 Massachusetts Ave, Cambridge, MA 02139) 

IF YOU’RE UP TO SPEED WITH POPULAR CULTURE

• MR. BARTLEY’S – The kitschy decor, riotous atmosphere, and extensive menu are but a few things to fall in love with at Mr. Bartley’s. The burgers are All-American and they don’t want you to forget it with each burger named after local personalities such as “The Joe Biden” and “The Tom Brady (Triumphant!),” Hollywood superstars like “Snoop Dogg” and “Beyonce (Hot!),” and anything relevant to current events like “The MBTA” and “Cuba.” With a menu that gives you an insight into Boston humor and onion rings to match, you won’t leave hungry or bored. And they keep the drinks retro— think: lime rickeys and frappes. (1246 Massachusetts Ave, Cambridge, MA 02138)

IF YOU WANT TO EAT AT A CELEB FAVORITE

• GOURMET DUMPLING HOUSE – Another spot where the long line is synonymous to good eats. This pan-Chinese single room restaurant has an overwhelming menu but you’d be an absolute fool to you miss out on their mini juicy dumplings, which are super-sized soup dumplings. There are only two kinds: pork and pork and crabmeat. If you want to get seated fast, don’t go with a large group. And I have to confess: their xiaolongbaos may be better than Din Tai Fung. Keep drinking the house tea to curb the bloating. (52 Beach St, Boston, MA 02111)

IF YOU NEED A MORNING PICK-ME-UP

The idolatry of coffee in Boston is obvious by the profuse amount of Dunkin Donuts shops found on every corner of the city.

• DUNKIN DONUTS – Dunkin Donuts is an institution in all of Massachusetts, providing cheap coffee on-the-go for the working/student populace. Greater Boston is also the birthplace of the premiere  coffee shop in the country. (543 Southern Artery, Quincy, MA 02169) 
• POLCARI’S COFFEE  – the most visited coffee joint in Massachusetts and is very photogenic on a downcast day. (105 Salem St, Boston, MA 02113)

IF YOU NEED TO STOCKPILE YOUR ARSENAL OF BAKED GOODS

Dessert shops in Boston warrant a larger conversation but here are some musts when you get to your dessert course.

• OMNI PARKER HOUSE has been pleasing crowds with their homegrown Boston cream pies since 1856 in the hotel restaurant. (60 School St, Boston, MA 02108)
• MODERN PASTRY (257 Hanover St, Boston, MA 02113) and MIKE’S PASTRY (300 Hanover St, Boston, MA 02113) are two Sicilian desert shops in The North End with whose claim-to-fame relies on their longtime feud. Everyone raves about the cannolis at Mike’s (hollow shells stuffed with sweetened ricotta cheese and studded with chocolate chips or pistachios), but the cannolis are arguably better at Modern Pastry. Get the lobster tails at Mike’s instead.
• FLOUR BAKERY by renowned chef Joanne Chang’s serves up perfectly glazed sticky buns decorated with chopped pecans. You can’t have just one. (1595 Washington St. Boston, MA 02118)
• TATTE BAKERY is an eatery heavily influenced by Israeli flavors that are dietary-restriction friendly—my suggestions: the lamb shakshuka, halloumi sunny side breakfast sandwich, and their flourless Halva brownies and cookies. (70 Charles St, Boston, MA 02114) 
• SOFRA BAKERY is a Middle-Eastern cafe with savory and sweet selections, but if you’re not afraid for new flavor profiles, try their Tahini Shortbread and Chocolate Hazelnut Baklava. (1 Belmont St, Cambridge, MA 02138)

✱ BLEACHER BAR – The most unique feature at Fenway Park is a bar built beneath the stadium bleachers. A floor-ceiling-window looking out onto centerfield gives bar guests an unbeatable view of the action, all from the vantage point of the Green Monster wall. Be prepared for a packed room on game days, but no complaints: you’re watching the game for the cost of a pint of beer. Sweet Caroline! (82A Lansdowne St, Boston, MA 02215)

✱ HONG KONG BOSTON – Faneuil Hall Marketplace is also a popular nightlife spot in the city and the dive bar not only has karaoke every night, but also the “Teriyaki Man” who peddles $1 sticks of chicken teriyaki on the dance floor to inebriated college students. (65 Chatham St Boston, MA 02109)

✱ LOOKOUT ROOFTOP AND BAR –  Rub shoulders with Boston’s YUPPIES (ie. Young Urban Professionals) at this Boston harborside rooftop bar inside the Envoy Hotel, which is surprisingly relaxed considering the type of clientele it panders to. Lines can get long so make sure to get there before 5 PM if you are planning to beat the after hours work crowds. (70 Sleeper St, Boston, MA 02210)

✱ THE SAMUEL ADAMS BREWERY – The local brewer has gained notoriety thanks to its free tour (although there is a suggested $2 donation to sample the brews from the test kitchen) but you get to bring home the collectible glass at the end. (30 Germania St, Boston, MA 02130),

✱ HARPOON BREWERY – Another crowd-pleasing brewery tour, renowned for their happening beer hall and famous pretzels! (306 Northern Ave, Boston, MA 02210)

✱ DOWNEAST CIDER HOUSE – Appealing to the gluten free population, this hard cidery is known for their inventive seasonal craft ciders, but you have to book in advance for their free tours that only run on the weekends. (256 Marginal St #32, East Boston, MA 02128)

EXPERIENCES

✱ THE LAWN ON D – Boston’s trendy outdoor event space has a calendar of public outings like movie screenings and beer fests. But people don’t go to “the lawn” just for the recreational activities; you cannot miss out on the swing installation, plastic rings  rigged with color changing LED lights. (420 D St, Boston, MA 02210)

✱ TD GARDEN – Boston is the uncontested sports capital of the United States and you must attend at least one sporting event while you’re there. If baseball is off-season, check out the TD Garden, which is also the regional commuter rail station, to see the Celtics play basketball or the Bruins play hockey. Boston earned its nickname “Championship City” due to every local sports team having won a championship in the last decade. (100 Legends Way, Boston, MA 02114)

✱ NEW ENGLAND HOLOCAUST MEMORIAL– Each of the six glass towers of the  symbolize a major extermination camp and are engraved with the identification numbers of the 6 million Jews that died at the hands of Nazi brutality.

✱ DUCK BOAT – By land or by sea: ride around Boston in a military-grade, amphibious, which drives straight into the Charles River for two different view of the city. Get tickets here.

✱ MAPPARIUM  – For anyone interested in the world, the exhibit in the Mary Baker Eddy Library is a stained glass, inside-out globe that is viewed from a 30-foot-long bridge. Also known as the “whispering gallery,” the curvature of the glass allows you to hear a person standing at the other end of the room perfectly. (200 Massachusetts Ave, Boston, MA 02115)

✱ CASTLE ISLAND  – Looking to take a leisurely stroll away from the chaos of the city? Enjoy a power walk at and around the historic Fort Independence. Short on time? Take the Castle Island Loop. If you have time to spare, try the Pleasure Bay Loop. (2010 William J Day Blvd, Boston, MA 02127)

PLACES TO VISIT

✱ BODEGA  – Calling all sneakerheads! This sportswear shop is hidden behind a fake Snapple vending machine that doubles as a sliding door when activated.  The vending machine is located in Latino-run convenience store, hence its name, eluding to a small grocery store in Spanish-speaking neighborhoods. (6 Clearway St, Boston, MA 02115)

✱ YUME WO KATARE – The concept is simple: finish your serving of ramen, announce your dreams to the whole restaurant. The logic is that if you can finish up the bowl, you can achieve anything you want in life. (1923 Massachusetts Ave, Cambridge, MA 02140)

✱ YUME GA ARUKARA – Just opened: the udon answer to Yume Wo Katare ^^ see above. (1815 Massachusetts Ave, Cambridge, MA 02140)

✱ TAZA CHOCOLATE FACTORY – A hipster chocolate factory known for their stoneground Mexican chocolate, with a compelling gritty texture, that you can buy in both disks and bars. Take a tour of the factory for only free $8 and get your money’s worth in free samples. (561 Windsor St, Somerville, MA 02143)

✱ FREE ART MUSEUMS –  More a modern art fan? THE INSTITUTE OF CONTEMPORARY ART (ICA) sits by the waterfront and is free every Thursday from 5:00 – 9:00 pm, while the extensive exhibitions of the all-encompassing MUSEUM OF FINE ARTS can be enjoyed for free every Wednesday from 4:00 – 9:45 pm.

BY METRO Boston’s main mode of transportation is none other than the MBTA, fondly known as “The T.” The T is the America’s oldest subway system (and sometimes it shows). It runs primarily underground but in some areas, goes above ground. The subway system is comprised of the Red, Orange, Green, and Blue Lines, with a Silver bus line that goes to the airport for the same cost as a standard ride. The fare per ride is $2.25. From Logan Airport, find the free Massport shuttles (Route Nos. 22, 33, or 55 to “MBTA Blue Line”) and then when you get to the Blue Line, you can ride the train to your final destination. To Logan Airport, take the Red Line to South Station, then transfer to the Silver Line Bus SL1, stopping at all terminals.

BY CARSHARING Lyft and Uber are the most popular carsharing applications in Boston. Taxi rates are astronomically much higher in comparison to carsharing so if you have mobile capabilities, use those apps. Uber’s surge charges during rush hour traffic are absurd so see check Lyft for better rates.

Boston is calling you! Continue building your to-do list with help from these resources!

Cool & Fun Things To Do in Boston by Thrillist

Things To Do in Boston That Are Fun & Free by Thrillist

Boston, MA’s Visitor Guide: What To See and Eat by Extra Petite

How To Spend Four Days in Boston by Nomadic Matt

Literary City Guide: Boston by Eat This Poem

👉 Have you ever been to Boston? Share your tips for seeing the city in the comments below!

Give me a shout-out on Pinterest pretty please?