Boston, Massachusetts: America’s Hub – Tip & Travel Guide

Do a Boston Vacation Like a Boss!

It’s a three-day weekend, and you want to pack in plenty of adventure without breaking the bank. How about Boston, baby? This is the third time for the Diostar Dumplings team, and we still can’t get over how awesome the city is! Despite the year-round blustery winds and frigid winters, which are said to top Chicago’s, Boston just keeps us going back for more wicked awesome waterfronts, all-around great attitudes, and fabulous food. Boston is either a mere two-hour flight or six-hour bus ride from Philadelphia.  If you book the 11 pm bus on a Friday, as we like to do, you’ll be able to catch a catnap and have a full day of fun ahead of you. Here is our Boston, Massachusetts tip & travel guide.

Boston Harbor

Getting Around

Boston MBTA or the “T‘ subway is your best bet. The public transportation in Boston run rather frequently. It is super fast and efficient and no panhandlers on the train! You do see the occasional dancing passenger, who likes to do the jitterbug in one place while gawking at his phone. It surely makes for a more entertaining commute, am I right?

Alevwife Station Boston

See Boston with Charlie!

A delightful token, known as the Charlie Ticket,  is valid for 24 hours and costs a mere $12.00 per person. Anyone, who planned to stay for five or more days can opt for the Charlie Card. (Think the New York metro card, the Smart Card in DC, or the Suica in Tohoku / Northeastern Japan). You can basically get anywhere riding the train. The red line train shall take you to Park Station or Downtown Crossing where historical charm and contemporary shenanigans marvelously collide.

Boston Charlie Ticket

Where to Stay

If your budget has enough wiggle room, the Omni Parker House is the place to stay in Boston. Originally built in 1855, it is located in the center city next to Boston Commons and by Park Station. The Omni Parker House is the epitome of Boston’s  historical charm and is also the longest continually operating hotel in the United States. With its lavish Victorian-style lobby and simple yet elegant rooms, Omni Parker evokes a glamorous lifestyle, without pomp or excess.

Omni Parker Hotel

Make It a Double, Parker!

We stayed at the Omni Parker Hotel during our first visit to Boston by snagging an amazing price at Agoda. On our second and third trips to Boston, we regularly swung by the Omni Parker to enjoy the ambiance, listen to jazz, sip a classic cocktail, and, of course, taste the decadent Boston cream pie at the very place it was invented!

Omni Parker Hotel

If Omni Parker is not in your price range, try AC Hotel in Cambridge. It is much less expensive than the downtown area, but make sure you book in advance during peak days. The rooms tend to fill up rather quickly.

AC Hotel Cambridge

AC Hotel Cambridge: Our Personal Villa in Boston

More modern and modest in its design, the AC Hotel belongs to the world-famous Marriott branch. The four-floor building felt somewhat closer to a privately-owned apartment, more so than a hotel. With its somewhat minimalist design, the AC Hotel Cambridge was quite a contrast from Omni Parker but definitely nothing to sneeze at, either. Apart from sprawling beds and roomy showers with fantastic water pressure (a crucial detail, to be honest), you have access to a complimentary *hydration station*, complete with a water-and-ice dispenser, as well as a microwave. (It’s useful to keep in mind, since our future stays will probably be at this very hotel; you never know when we would stumble upon a street food market treat, which we may or may not save for later, so a microwave will come in handy– as will the mini-fridge in the room, itself).

AC Hotel Cambridge Room

Tucked away from the hustle and bustle of downtown Boston, the AC Hotel is a short, scenic walking distance from the Alewife Train Station; You reach it after walking along a serene, winding trail through the Alewife Brook Greenway.

Alevwife Brook Greenway


Bunker Hill Monument

The Freedom Trail ends at the Bunker Hill Monument, one of the city’s most renowned landmarks. The BHM was originally erected in 1794 to commemorate the valor and determination of the Colonial militia against the Redcoats during the Battle of Bunker Hill. The structure boasts a series of breathtaking views, which you can witness while climbing all of its glorious 294 steps to the top. The experience is guaranteed to put you in scenic overdrive, not to mention get your heart racing a bit. (The climb down the spiral steps might be easier on your legs, but it is sure to make your head spin (hopefully in a good way). We probably will do it again on our next visit!

Bunker Hill Monument

The Freedom Trail

The Freedom trail has many enticing historical stops, starting from Boston Commons,where the famed Freedom Trail starts: A narrow, brown brick road built in 1951, it winds between Boston Common to the USS Constitution and Charlestown. Remember the Midnight Ride of Paul Revere? His house, along with the resting place that bears his name, is one of the stops. History buffs and outdoor enthusiasts will find plenty to scout out around the Boston Common area. If the mood strikes, venture inside Faneuil Hall, built by merchant and entrepreneur Peter Faneuil.The renowned marketplace has held meetings and conferences since 1743, including numerous speeches by Samuel Adams (Take note, beer lovers!) and RFK’s Presidential candidacy announcement.

Freedom Trail

Faneuil Hall

Definitely, don’t miss out on out Faneuil Hall  You can reach it either by a 10-15 minute walk to Boston Commons, or by the ‘T’ subway at Park Station to the Green Line, which shall take you to Government Center Station. While there,  stroll through the historic Quincy Market, which is as iconic to Boston as the Reading Terminal Market is to Philadelphia. Browse the selections of the freshest produce; sample Boston’s beloved treats, and simply chill out. Quincy Market is the ideal hiding spot to catch a reprieve from the pesky windchill. (Our first Boston visit was during the winter, and boy were we glad to have discovered the Quincy Market! The Boston Public Library is not too shabby, either: Floors upon floors containing a staggering collection of literature, the Boston Public Library feels like the bibliophile’s Louvre: Basically, you can spend days upon days in this place, and still, there will be much left to discover… Sounds like the perfect excuse– one of many– to keep revisiting Boston, time after time.

Boston Quincy Market

Tip: Be on the look out for Fake Monk Mafia; they are usually around Faneuil Hall or around the Harbor Side area. They are not real monks. Do not give them any money.

Fake Monks Mafia

Boston Harbor

Third time’s the charm at the Boston Harbor! During this visit, we finally chanced on a day with less of a windchill and more sunshine, so we could enjoy a stroll on this iconic boardwalk. The water is looking fine, too; looks like they cleaned up the area quite well after the Boston Tea Party!

Boston Harbor

Boston Commons

Boston Commons is the oldest public park and the center of historical landmarks, such as the Massachusetts State House, which was featured in  ‘The Departed‘, a remake of the Cantonese-language blockbuster, Infernal Affairs.

Massachusetts state house

SoWa Art + Design District

Watch out, Philadelphia: Boston’s art scene is pretty snazzy at the Sowa and Design District! We heard on a whisper about a street festival near the North End neighborhood (Boston’s Little Italy) and chanced upon the SoWa (South of Washington) Art & Design District. The area is studded with funky galleries that feature works by the city’s hottest contemporary artists, as well as hip restaurants and retro-cool boutiques that specialize in everything from vintage fashions to vinyl records, with a bit of modern bric-a-brac thrown in the mix.

Boston SoWa

Shop and Sip in SoWa

From one stall to the next, vendors try to outdo each other with their inventive merchandise. Feasting our eyes on the unique works of art sure has made us thirsty! Luckily, a lively team of local brewers treated us to several varieties of homemade mead (honey-based liquor). It is said to be the oldest alcoholic beverage in the world (alongside beer, of course), an the selections at SoWa were smooth and robust, all at once. I am glad to have given mead another chance; my very first taste of the drink, years ago, was a cloying mess, to say the least. (A bit of trivia for Russian-speakers: Whenever a children’s story featured a feast, and the characters happened to be drinking *honey*, it was actually mead!)

SoWa Market

Step inside the Sowa galleries, shops & art studio. From the basement of vintage goods, to 4 floors of amazing art gallery studios, the eye candy is plentiful.

SoWa Art Galleries

Tons of super-talented artists– from photographers and painters to designers– showcased their creations. This one in particular is Paula Ogier Artworks, Check out her collection!

Paula Ogier Artworks

Make the wall your canvas! Future artists at work.

Boston SoWA Art

Boston Museum of Fine Arts

Up for some color, whimsy, and creativity? Right this way to the Museum of Fine Arts (MoFA, as I call it): The Red-to-Green Line transfer shall take you to the Museum Arts Station in no time.

Boston Museum

Places to Eat

Bagelsaurus…Couldn’t resist another couple savory sandwiches at this place. 🙂


Amsterdam Falafel Shop

Amsterdam Falafel Shop is a healthy eater’s dream, this low-key restaurant encourages you to play with your food. Start off by crushing the (falafel) balls inside the pita pocket, then go rogue with as many fillings as you want! The menu is a vegetarian’s paradise, so delicious that even hard-core carnivores dig in with gusto.

amsterdam falafel

Neptune Oyster Lobster Roll

You cannot do a Boston trip without ordering a lobster roll, at least once! The sandwich served at the famous Neptune Oyster restaurant was worth the wait, even if slightly overpriced…. Not that there’s anything wrong with that! You’re on vacation in Boston, so treat yourself. The roll was definitely delish: Enormous chunks of lobster meat on a soft, buttered roll were right on the money.

Neptune Lobster Roll

Durgin Park

Try their signature Baked Beans. The nation’s second-oldest restaurant is partly responsible for Boston’s quirky moniker of *Beantown*. Located in the Faneuil Hall Marketplace, Durgin-Park has secured its iconic status since 1827.

Boston Baked Beans

Oysters— the freshest, most succulent raw oysters we have tasted.

Durgin Park Raw Oysters

Baked Oyster— savory goodness with a pleasantly briny kick, under a fluffy blanket of creamy butter and Parmesan panko.

Durgin Park

There are also known for their Prime Rib Steaks. (Note to self: We’re definitely coming back to Durgin-Park to try these. 🙂 )

Durgin Park Steaks

Boston Sail Loft

Clam Chowder…This is it: Boston in a bowl, served at the Boston Sail Loft. The signature velvety soup had  just the right balance of flavorsome seafood broth and a faintly sweet heavy cream. We’re talking about genuine clam chowder with sizable, meaty clams. No microscopic, Progresso-style, clam-flavored pixie dust here! Grab a table by the window, order a pint of Samuel Adams– Boston’s iconic ale– and watch magnificent yachts sailing and docking.

Boston Clam Chowder

Not that the majestic bowl of clam chowder needed any embellishment, but we threw in a couple oyster crackers, for good measure. The result was a symphony of crunchy, miniature puff pastry-like shells soaking up the seafood ambrosia.

Boston Clam Chowder

Mike’s Pastry

Boston’s timeless “home of the cannoli” has been making mouths water and lines eagerly loop around the block since 1946. You think you’ve tried the best mascarpone pipe ever? Better get your hands on one, six, or dozen of these, so you don’t miss out on any of their scrumptious fillings. Mike’s Pastry really steps outside vanilla box with limoncello, strawberry, chocolate, Nutella, chocolate chip, Oreo, pistachio, and then some. Trust us: The lines never go down, and they’re worth the wait every time.

Mikes Pastry

Aside from their famous Cannolis, there other pastries are top notch as well!

Mike Pastry

Couldn’t pass on these bad boys. (Featured on the plate: limoncello, oreo, pistachio, and chocolate chip.)

mikes pastry cannoli

Cookie Monstah

Ice cream and cookies together? Yes, please! We’re talking about more than a simple ice-cream sandwich. What began as a family-run food truck grew into a city-wide sensation. Insomnia Cookies in Philadelphia are tasty, but Boston has the upper hand with its creations: M&M, chocolate chip, pumpkin pie… We ordered a blueberry pie ice-cream to go with our cookie:  enormous chunks of sweet, crunchy pie crust and juicy blueberries. My mouth is watering, just writing about Cookie Monstah!

Cookie Monstah Icecream

Boston Cream Pie

Of course, it isn’t a Boston vacation, until you have tasted the Boston Cream Pie.  The only place to find the real deal is the Omni Parker: You can buy it either inside Parker’s Restaurant at the Omni Parker Hotel or at the gift shop. A pie this size costs roughly $8.00. Totally worth it!

Boston Creampie

Boston: A Wicked Smaht City

We hope that our guide to Boston on a Budget will be a fun and useful tool for your vacation. Whether it is your first trip or a one of many, this city will surely leave a mark of wicked awesome experiences. Make sure to visit the city in the summer, but if you cannot wait, do bundle up. Whether indoors or outdoors, Boston always has plenty to do, see, taste, and love.

Alevtina Gefen
Alev Gefen

Hi, I'm Alev. I am a linguaphile, travel fiend, and foodie. I love diving deeply into culture through its authentic foods, especially when sharing meals with the local people in every country I visit. Whether at a table or by a street food stall, I love it all, and writing about the experience is half the fun!

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