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Caroline in the City Guide to Boston


The Red Sox, the Tea Party, baked beans, and Good Will Hunting may be the first things that come to mind when you think of Boston, Massachusetts, but there’s so much to the city beyond the tourist zones. Sure, it’s rich in history, dating back to the early days of America. Visitors can walk the footsteps of Paul Revere and Samuel Adams. The city is also surrounded by water and has a National Parks site made up of their barrier islands. There’s also an arts culture found in the museums and galleries, easily explored on foot or via public transportation. Boston is the perfect base for adventures throughout Massachusetts and beyond. Hop aboard a train or rent a car to explore Cape Cod and the Berkshires.


Harvard campus in Cambridge

The Neighborhoods

Boston is a fairly spread out city, but you wouldn’t know it based on how easy it is to get around. Most attractions are located downtown and in Beacon Hill, but unique neighborhoods are only a short walk or train ride away. Here, you’ll feel like you could be in a different city entirely.

Chinatown was where I based myself for my trip, a highly underrated part of the city, especially for those on a budget. You can still get a $3 pint or a $5 meal. But in addition to the classic eateries, newer ones have also popped up. Trendy coffee shops and boutiques are also making their way into the area.

Despite its namesake, Fenway-Kenmore is much more than the Red Sox. Museums like the Museum of Fine Arts and the Isabella Stuart Gardner Museum are located here, along with a number of college and university buildings.

The Seaport district has so many great restaurants that you could spend your entire trip just eating here. Pick up craft beer to go from Trillium Brewing Company, check out the public art, and generally just wander.

A friend referred to Back Bay as her favorite neighborhood and judging by the Victorian brownstone homes, I can see why. Around Copley Square, you’ll find Trinity Church, the Boston Public Library, and green spaces to sit and people watch.

Cambridge, home to Harvard University and Massachusetts Institute of Technology, has a number of student-friendly eateries and businesses. Grab a show and dinner at The Sinclair. Browse the secondhand shops for unique clothing items and roam the campuses to soak up all the brain power.


Pork buns at Shojo

Restaurants and Cafes

Most travelers seek out places like Union Oyster House and the kitschy Italian restaurants of the North End, but you can find just about every type of food in Boston. There are so many great places to eat, so plan accordingly.

Shojo Boston– My first meal in Boston was at this modern Asian eatery in Chinatown. It has funky murals on the walls and dishes like the pictured pork belly buns, duck fat fries, and kimchi fried rice, along with Japanese beers, sake, and cocktails.

Mike’s Pastry – Boston– In the battle of Modern vs. Mikes, I went with Mike’s. I have zero dog in this fight, but just make sure you get cannolis while you’re in Boston. Be prepared to wait in line at either establishment and know what you want before reaching the counter.

Blackbird Doughnuts– On our way out of town, I ran to get donuts at this local cafe, which had flavors like Boston cream, everything bagel, and their signature Blackbird on brioche dough. They also have coffee, the perfect pairing.

Dig Inn– After some heavy meals, we ate at this regional chain for lunch. You basically make your own bowl of goodness of healthy, local dishes. Start with your base of rice, quinoa, or salad and top with whatever is fresh that day.

Red’s Best Fish Market & Eatery– I had a killer lobster roll at the Boston Public Market at this stall. I’m not usually a fan of cold seafood, but the warm buttery bun was the perfect combination and totally satisfying. They also sell seafood to take home, caught locally by fishermen.

Rigoletto Ristorante– A local friend recommended getting away from the North End’s main drag to avoid overpriced restaurants, so my sister Yelped this restaurant. It was cozy and had a big open window overlooking the street. I had a glass of wine and a bowl of pappardelle with Italian sausage.

Gourmet Dumpling House– Where Shojo is new-age, Gourmet Dumpling is old school. You’ll likely have to wait for a table, but soup dumplings, scallion pancakes, and other Chinese deliciousness will greet you.

Townsman– Located near the Greenway, this colorfully decorated space has received awards for its brasserie style fare with a local twist. Start with New England oysters and share small plates of meats, cheeses, and other dishes between friends.

K O Catering & Pies– Finding Australian goods in America is a favorite pastime, so I’m bummed I didn’t find out about KO until later. The cafe sells authentic Aussie meat pies along with Anzac biscuits, lamingtons, and other items from Down Under.

Row 34– Seafood heaven is at this modern raw bar and restaurant. Clam chowder, lobster rolls, and whole cooked fish are must try dishes. They also carry a diverse wine list that will pair perfectly with your chosen bivalve.

Temazcal Tequila Cantina– How many Mexican restaurants can say they have views like these? Guacamole is made fresh daily, paired with tacos, salads, fajitas, and enchiladas. Choose from the extensive tequila selection for your margarita or have it neat.

Tatte Bakery & Café– This popular farmers market stall has now become a successful local business with locations in Boston, Brookline, and Cambridge. Open for breakfast and lunch, the menu has baked goods as well as salads, sandwiches, and dishes inspired by the owner’s Israeli heritage.

For more of the best places to eat while visiting Boston, check out Eater’s essential list


Harpoon Brewery

Bars and Nightlife

Most visitors stick to Boston’s sports and Irish bars, of which there are plenty. But you can also find swanky cocktail bars, craft beer establishments, and everything in between, whether you’re looking for one drink or an all-night bender. And because of blue laws, there is no happy hour anywhere in the city.

Biddy Early’s– I visited this dive on a pub crawl and was amazed at how cheap the drinks were. The $2-3 pints of beer are best enjoyed at a table while watching the Red Sox. It’s certainly nothing fancy and the bathrooms leave something to be desired.

Bleacher Bar– When you can’t get seats to the Red Sox game, or they’re charging $75 for nosebleed seats, this is your best bet. There’s a grate through which you can see the outfield. You can’t take pictures during games and there’s a time limit to sit there. Grab a local beer and pastrami sandwich.

Harpoon Brewery & Beer Hall– Located in the Seaport area, this brewery operates in Boston and Vermont. The taproom overlooks the harbor offering IPAs and other American ales along with pretzels to share. They also have an outdoor beer garden open seasonally.

L Street Tavern– Have a pint where Matt Damon and Ben Affleck pick up college girls in Good Will Hunting. Here you’ll find photos from the film and locals enjoying sports on television. They don’t offer food, so eat in advance.

Lookout Rooftop and Bar– Soak up the skyline at the rooftop of the Envoy Hotel. Indoor and outdoor spaces make it a neighborhood favorite year-round. Wine, beer, and craft cocktails all make up the menu, along with light bites.

Yvonne’s– This moody supper club is set in the former space of a 1800s cellar cafe, covered in funky art and chandeliers. The speakeasy vibe has shared plates like flatbreads along with strong craft cocktails.

Jaho Coffee Roaster & Wine Bar– During the day, this place is full of laptops and people waiting for their pour over coffee from the laboratory-looking setup. At night, it’s a wine bar that also offers their famous Scarlet Espresso Martini.

Highball Lounge– For a retro-inspired atmosphere, check out the vintage games and colorful cocktails at the Kimpton hotel. They serve their own versions of bar food along with regional beers, best played over a round of Hungry Hungry Hippo.


Fenway Park

Things to Do

There are so many attractions for first-time visitors to Boston. Save time and money with the Boston CityPass if you plan on hitting the highlights like Faneuil Hall, the Paul Revere House, the Boston Children’s Museum, and the New England Aquarium. I also recommend touring Fenway Park because it’s one of the oldest stadiums in major league baseball. But if you’re looking for something a little different, here are the attractions I was drawn to during my visit.

Free Walking Tour– This tour company offers tips-based walking tours all over the city, including the Freedom Trail, Harvard, and Beacon Hill.

Boston Public Library– It’s free to visit this stunning space. Stop by for free WiFi and refill your water bottle. Their garden is one of the most beautiful places to have lunch.

Harvard University– Tour one of the country’s most beautiful campuses. You can take an organized tour or pick up a brochure that points out landmarks. Harvard has a number of exhibits and museums you can visit for free as well.

Boston Common– Experience one of Boston’s most famous green spaces, home to the swan boats and the “Good Will Hunting” bench.

Isabella Stewart Gardner Museum– Founded by a wealthy local woman, Gardner had this Italian style villa built to hold all of her Renaissance treasures from her travels. Give yourself time to explore their modern wing and have lunch at the stylish cafe.

Museum of Fine Arts– To see a diverse collection of classic pieces, including an Alexander Calder mobile, a Van Gogh painting, and Chinese sculpture, look no further than the MFA.

John F. Kennedy Presidential Library and Museum– A bit further afield, the JFK Library documents the life of the 35th president that hailed from Massachusetts.

Classic Harbor Line– Hop aboard a sailboat for a cruise around the Boston Harbor. Purchase drinks to enjoy as you see the surrounding islands.

Arnold Arboretum of Harvard University– Another green space is this Frederick Law Olmsted-designed arboretum further out of town. Run by Harvard University, species of plants are studied here.

Boston TV & Movie Sites Tour– See where your favorite movies and television shows were filmed with On Location Tours. Cheers, Fever Pitch, and Legally Blonde are all featured.


Brattle Bookshop


Pick up unique souvenirs for yourself around the city. In addition to the chain stores like Primark in Boston, there are a few local spots to shop around.

Boston Public Market– In addition to the food stalls, this local market sells gifts like wooden bowls, yarn, craft beer, tea blends, and flowers.

Brattle Book Shop– This beloved bookstore sells used paperbacks for $1 in the alley next to the building as well as rare first editions that will cost you thousands. Give yourself plenty of time to roam.

The Taza Chocolate Bar– Organic chocolate is made in nearby Somerville and sold throughout the city. Sample the unique combinations like Mexican chocolate, salted almond, and chipotle chili.

SoWa Open Market– Held every weekend on the Greenway, this is the best place to buy local goods from makers like my friends at Speakeasy Travel Supply! They also have food trucks and musical performances.

Society of Arts and Crafts– The organization that has been supporting artists since the 1800s has a gallery space in the Seaport where your purchases support the members.

Quincy Market– It’s a tourist trap, but worth a peruse if you are looking for Boston themed gifts and souvenirs and locally made products. The building dates back to the 1800s and also has restaurants inside.

Shake the Tree– Shop for women’s clothing and jewelry, home goods, paper goods, candles, cocktail supplies, cookbooks, and other gifts at this trendy North End boutique.

Castanet– You never know what designer pieces might be hiding in plain sight at this consignment store.

Copley Square Farmers Market– I happened upon this market while exploring Back Bay. It had food stalls as well as fresh flowers, produce, and food trucks.


HI Boston

Where to Stay

There aren’t as many affordable options in Boston as you’ll expect to find in bigger cities so this might be a place to splurge.

HI Boston Hostel– My base for the trip was Hostelling International’s Boston outpost, which has won awards for its amenities. Dorms and private rooms are available, which come with comfortable mattresses, linens, reading lights, and charging stations. Also included are complimentary breakfast, WiFi, daily tours and activities, a full kitchen, lockers, and a game room. Bicycles can be rented for exploration. It’s located in Chinatown within a short walk from public transportation and most of the city’s attractions. They’ve also taken steps to reduce their carbon footprint with recycling and other programs.

40 Berkeley– Located in a historic South End building, this property also has dorm rooms. Amenities include communal spaces with fireplaces and pool tables, hallway bathrooms, free linens, free WiFi, laundry facilities, a movie room, and 24-hour assistance at the front desk.

YOTEL Boston– The brand of pod hotels has a new location in Boston. Set in the Seaport District, Yotel has a rooftop bar and restaurant. Rooms are small, but the amenities add to the value, including WiFi, premium toiletries, adjustable beds, flat screen televisions, and city views.

AMES HOTEL– This award-winning boutique hotel is in the heart of the city, furnished with art pieces relevant to the location, a historic skyscraper. Ames has free WiFi, a fitness center, and an in-house restaurant.

XV Beacon Hotel– Another luxury boutique option is XV Beacon in a Beaux Arts style building in Beacon Hill. A fitness center, WiFi, gas fireplaces, flat screen televisions, and rainforest shower heads are among the features.

Peddocks Island– As a part of Boston Harbor Islands National and State Park, adventurous visitors can stay overnight at rustic campsites or in one of six yurts. Open seasonally, reservations are required.

Don’t forget about Airbnb as an option either, which will allow you to stay in different neighborhoods to explore Boston.


Tram in Fenway


Arriving at Boston Logan airport, we decided to hop in a Lyft and save a half hour on the bus. It cost around $14, which I split with my sister, and there was an organized area for rideshare passengers to be picked up. Just double check the license plate as apparently black Toyota Corollas are popular cars. Get a discount on your first ride by using the code “CAROLINE868074”. 

Alternatively, there’s a free Silver Line bus that runs between the airport and South Station. South Station is also where buses like Megabus, Peter Pan, and Greyhound depart and arrive as well as Amtrak and commuter trains.

Overall, Boston is a highly walkable place and all of the big attractions can be seen without ever hopping in a car. There are also bike shares around town known as Hubway. I’d heard stories about Boston’s public transportation system, known as “The T,” but thankfully it runs many places that I needed to go. The only part I found confusing was “outbound” vs. “inbound” instead of displaying the end point or area like the subway does in New York. Subway, ferry, and bus trips cost around $2 each way, depending on if you pay individually or on a Charlie Card. I recommend getting a card to fill up for your stay.

And since my trip did not end well thanks to canceled flights, I highly recommend getting Travel Insurance, even for short trips. Paying for changed flights or hotel rooms out of pocket is not ideal! I recommend World Nomads.



Mentioned in this post
  1. Trillium Brewing Company
    Attraction in Suffolk County Massachusetts

    Suffolk County Massachusetts
    (617) 453-8745
  2. The Sinclair
    Attraction in Cambridge Massachusetts

    52 Church St.
    Cambridge Massachusetts
    (617) 547-5200
  3. Shojo Boston
    Restaurant in Suffolk County Massachusetts

    9 Tyler St
    Suffolk County Massachusetts
    (617) 423-7888
  4. Mike's Pastry - Boston
    Restaurant in Suffolk County Massachusetts

    300 Hanover St
    Suffolk County Massachusetts
    (617) 742-3050
  5. Blackbird Doughnuts
    Restaurant in Suffolk County Massachusetts

    492 Tremont St
    Suffolk County Massachusetts
    (617) 482-9000
  6. Dig Inn
    Restaurant in Suffolk County Massachusetts

    277 Washington St
    Suffolk County Massachusetts
    (617) 276-1000
  7. Red's Best Fish Market & Eatery
    Restaurant in Suffolk County Massachusetts

    100 Hanover St
    Suffolk County Massachusetts
    (617) 830-1672 ext. 122
  8. Rigoletto Ristorante
    Restaurant in North End Boston Massachusetts

    115 Salem St
    North End Boston Massachusetts
    (857) 350-3402
  9. Gourmet Dumpling House
    Restaurant in Suffolk County Massachusetts

    52 Beach St
    Suffolk County Massachusetts
    (617) 338-6223
  10. Townsman
    Restaurant in Suffolk County Massachusetts

    120 Kingston St
    Suffolk County Massachusetts
    (617) 993-0750
  11. K O Catering & Pies
    Restaurant in Boston Massachusetts

    256 Marginal St
    Boston Massachusetts
    (617) 418-5234
  12. Row 34
    Restaurant in Boston Massachusetts

    383 Congress St
    Boston Massachusetts
  13. Temazcal Tequila Cantina
    Restaurant in Boston Massachusetts

    250 Northern Ave
    Boston Massachusetts
    (617) 439-3502
  14. Tatte Bakery & Café
    Restaurant in Suffolk County Massachusetts

    70 Charles St
    Suffolk County Massachusetts
    (617) 723-5555
  15. Biddy Early's
    Restaurant in Suffolk County Massachusetts

    141 Pearl St
    Suffolk County Massachusetts
    (617) 654-9944
  16. Bleacher Bar
    Restaurant in Boston Massachusetts

    82A Lansdowne St
    Boston Massachusetts
    (617) 262-2424
  17. Harpoon Brewery & Beer Hall
    Attraction in Boston Massachusetts

    306 Northern Ave
    Boston Massachusetts
    (617) 456-2322
  18. L Street Tavern
    Restaurant in Suffolk County Massachusetts

    658 E 8th St
    Suffolk County Massachusetts
    (617) 268-4335
  19. Lookout Rooftop and Bar
    Restaurant in Suffolk County Massachusetts

    70 Sleeper St
    Suffolk County Massachusetts
    (617) 338-3030
  20. Yvonne's
    Restaurant in Suffolk County Massachusetts

    2 Winter Pl
    Suffolk County Massachusetts
    (617) 267-0047
  21. Jaho Coffee Roaster & Wine Bar
    Restaurant in Suffolk County Massachusetts

    665 Washington St
    Suffolk County Massachusetts
    (857) 233-4094
  22. Highball Lounge
    Restaurant in Suffolk County Massachusetts
  23. Fenway Plaza
    Suffolk County Massachusetts

    Fenway Plaza
    Suffolk County Massachusetts
  24. Boston Public Library
    Attraction in Boston

    700 Boylston St
  25. Harvard University
    Attraction in Cambridge Massachusetts

    12 Holyoke Street
    Cambridge Massachusetts
    (617) 495-1000
  26. Boston Common
    Attraction in Boston Massachusetts
  27. Isabella Stewart Gardner Museum
    Attraction in Boston Massachusetts

    280 Fenway
    Boston Massachusetts
    (617) 566-1401
  28. Museum of Fine Arts Promenade
    Suffolk County Massachusetts

    Museum of Fine Arts Promenade
    Suffolk County Massachusetts
  29. John F. Kennedy Presidential Library and Museum
    Attraction in Boston Massachusetts

    Columbia Point
    Boston Massachusetts
    (617) 514-1600
  30. Arnold Arboretum of Harvard University
    Attraction in Suffolk County Massachusetts

    125 Arborway
    Suffolk County Massachusetts
    (617) 524-1718
  31. Brattle Book Shop
    Attraction in Suffolk County Massachusetts

    9 West St
    Suffolk County Massachusetts
    (617) 542-0210
  32. The Taza Chocolate Bar
    Restaurant in Suffolk County Massachusetts

    100 Hanover St
    Suffolk County Massachusetts
    (617) 623-0804
  33. SoWa Open Market
    Restaurant in Suffolk County Massachusetts

    460 Harrison Ave
    Suffolk County Massachusetts
    (857) 362-7692
  34. Society of Arts and Crafts
    Attraction in Suffolk County Massachusetts

    100 Pier Four Blvd
    Suffolk County Massachusetts
    (617) 266-1810
  35. Quincy Market
    Attraction in Suffolk County Massachusetts

    206 S Market St
    Suffolk County Massachusetts
  36. Shake the Tree
    Attraction in Suffolk County Massachusetts

    67 Salem St
    Suffolk County Massachusetts
    (617) 742-0484
  37. The Closet is now Castanet
    Attraction in Suffolk County Massachusetts

    175 Newbury St
    Suffolk County Massachusetts
    (617) 536-1919
  38. Copley Square Farmers Market
    Restaurant in Suffolk County Massachusetts

    139 St James Ave
    Suffolk County Massachusetts
    (781) 893-8222
  39. HI Boston Hostel
    Hotel in Suffolk County Massachusetts

    19 Stuart St
    Suffolk County Massachusetts
    (617) 536-9455
  40. 40 Berkeley
    Hotel in Suffolk County Massachusetts

    40 Berkeley St
    Suffolk County Massachusetts
    (617) 375-2524
  41. YOTEL Boston
    Restaurant in Suffolk County Massachusetts
    Restaurant in Suffolk County Massachusetts

    11 Parmenter St
    Suffolk County Massachusetts
  43. XV Beacon Hotel
    Hotel in Boston Massachusetts

    15 Beacon Street
    Boston Massachusetts
    (617) 670-1500
  44. Peddocks Island
    Attraction in Plymouth County Massachusetts

    Plymouth County Massachusetts
  45. South Station
    Suffolk County Massachusetts

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One Response to Caroline in the City Guide to Boston

  1. Charles McCool September 19, 2017 at 7:13 am #

    Magnificent guide to Boston. So many new places for me to try. My current favorite place is not listed but that is fine. I like it to remain a relative secret.

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