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Special thanks to Ricky Capelluto and Danielle Hare for the recommendations.

Rich in Colonial history and hardcore sports fandom, Massachusetts is a proud pocket in the north eastern United States. Not just Tom Brady and clam chowdah, this state is the mecca for American Revolution history and Ivy League institutions. Whether you want to be a part of the passionate and rowdy city of Boston or retreat to the upscale harbors of Cape Cod, Massachusetts has a scene for just about anybody.

Revere Street

Boston Common

Boston Common

Newberry Street


Boston Common

Cathedral, Boston

Tatte Bakery

Boston Marathon Start Line

Boston Common

Boston Common




Beacon Hill: Historic area with really picturesque, old brick houses. Classic lanterns lights create an amazing atmosphere during the fall. Check Charles St. for cute retail.


North End: Lively Italian district with lots of authentic restaurants. Rumored that until 1999 most businesses were still accepting Italian Lira for currency.


Seaport: New up-and-coming area that sits right on south Boston's waters. Lots of cool hotels, restaurants, rooftop bars, and plenty more currently being built.


Back Bay: Affluent area just west of Boston. Tons of nice hotels accompanied by all the bougie retail (Boylston and Newberry).


South Boston: “Southie” is where all the old Boston mob action in movies took place. Since then, it's transformed into a modern, hip area with a lot of youngsters. Don’t know a ton of bars down there, but there’s definitely some good ones.


West End: Handful of contemporary bars and TD Garden


Financial District/Downtown Crossing/China Town: Outside of business, not much to see here. Some cool views from the skyscrapers in the financial district if you can find your way up. Downtown crossing is “in transition” and used to be sketchy, but has some really nice new condos and hotels popping up. Call it gentrification, but China Town also has some good restaurants.


South End: Plenty of quality restaurants for all taste buds. See Beehive and Barcelona below.


Fenway: Home to the Sox, Fenway Park, and the best sports bars in town.

Things to Do

Fenway: Redsox games are really fun, and Fenway is one of the most historic stadiums for anyone into baseball. If you're willing to throw down for tickets you can get sick seats on top of the green monster for around $120 or $40 in the cheap seats. Also do tours of the park if you can't catch a game. The Fenway Summer Concert Series is always a blast with names ranging from Zac Brown Band to Elton John to Paul McCartney!


TD Garden: Whether you are catching a Bruins or Celtics game, or a big headlining concert this is a great place to spend a day or night!

Harpoon Brewery, Seaport: New brewery with a cool beer hall, and tours of their taproom, etc.


Boston Common/Boston Garden: Clean park right in the middle of Boston that dates back to the 1600s. The pond in the garden freezes over during the winter and you can walk on it, which is pretty cool. During the summer they rent paddle boats.


Hubway: Bike sharing service with stations all over the city. Rent a bike and ride along the Charles River or any part of the city you want! We recommend starting in the west end by Old Charles River Dam and ride west (either side of the river). Beautiful on a spring/summer day. If you’re up for it, you can follow the path all the way past MIT, Boston University and Harvard. The bikes are a great way to get around. (This bullet point sponsored by Hubway™).


Historical Sites: There’s a ton of revolutionary era history to soak up. Graveyards with American presidents, the channel where they dumped the tea during the Boston tea party, the Boston massacre site, old churches, Paul Revere's path and much more! v.


Fanueil Hall: Very touristy, but for good reason because it's one of the oldest markets in the United States. Still a cool building but basically just packed with expensive food-court type food and people.


Harvard: Take a stroll through this beautiful and revered Ivy League campus.


Shopping on Newberry and Boylston in Back Bay: Both of these streets are packed with cool stores, experimental pop-up shops, and much more. Prudential Center on Newberry is the main mall.

Commonwealth Avenue: “Comm Ave” extends just west of the Boston Garden and is lined with nice houses on either side as you make your way towards Back Bay.


Improv Asylum: Quaint, comical, improv comedy club in the north end. Intimate setting.

New England Aquarium: Aquarium home of Myrtle the Turtle! Beautiful stonework on the outside and great place to spend some time.

Freedom Trail: A 2.5 mile-long trail through downtown Boston that includes 16 historical locations vital to United States history.

Underground at Ink Block: Instagrammable walking trail with tons of art and graffiti.

House of Blues: Concert venue across the street from Fenway Park. Big name bands and DJ’s can often be found here.

Places to Eat

Tatte: Good brunch spot on Charles Street in Beacon Hill. Usually hard to find a place to sit but great Croque Monsieur, their farro dish, coffee, pastries ect. Pardon the French, but it's a basic bitch's paradise.


Legal Sea Foods: There’s a ton of them around Boston. Fantastic oysters, drinks, and seafood. The Seaport and Harborside locations are our two favorites because they're right on the water. 


Beehive: Dank drinks and food with live jazz/RnB/Reggea music. Great date spot.


Mike’s Pastries: Extremely long lines but well worth it.


Bricco: Fancy Italian restaurant in the north end.


Eataly: Dope Italian supermarket with roughly 5 restaurants inside. Restaurants and markets are expensive, but insanely good.


Top of the Hub (Prudential Tower): The food is okay, but you're really coming here to catch the incredible view.

Santarpio’s: To tourists, it's dubbed “where the locals eat.” Located in East Boston close to the airport, enjoy a large pie and a side of lamb for a quick and delicious meal. This restaurant is CASH ONLY so make sure you're prepared!

Quincy Market: A small market in a cobblestoned area filled with a wide variety of foods. Make sure you grab some clam chowdah while there!

Wahlburgers: Now a successful chain, the flagship restaurant is in Boston. The reality show Wahlburgers also films here from time to time if you're trying to catch Marky Mark and the brothers.

Places to Drink

Lollitas: One location in Back Bay and one near Seaport, this tequila bar/restaurant has some refreshingly spicy margs.


Yotel: Tight (like its dope, not like its small) rooftop bar in Seaport.


Envoy: Another cool rooftop bar in Seaport. Seaport is always good for some harbor views.


Yvonne’s: Awesome speakeasy that opens up into a massive bar/restaurant. Really good food coupled with expensive drinks, but validated by their unique mixology. Décor is really esoteric, it's a must-see.


Whiskey Saigon: Poppin' nightclub, usually has a cover.


Scholars: Bit of a go-to spot for those in Downtown Crossing. Pool tables upstairs and dance floor downstairs.


Tia’s: Cool spot outside by the waterfront. Thursday spot during the summers. PACKED. Usually people head there early/after work.  


Bell in Hand: Vast dance floor, only problem is you usually have to wait in line to get in, and then wait in line again to get upstairs. Would advise going early.


Black Rose: Little bit of an Irish dive bar. You can tell it’s got a lot of history. All the servers have Irish accents, and the establishment playa live Irish folk music. Expect people to get up and Irish dance, it gets pretty wild.


West End Johnny’s: “Wedge” kind of rowdy. Usually does rap music upstairs and live country downstairs. 


The Tunnel: Truly unique place. Go when you’re trying to get weird.

Hong Kong: Bar in Faneuil Hall next to Wild Rover. Karaoke and Scorpion Bowls are the main attraction here. Stay late enough and a waiter will walk around selling $1 Chicken Teriyaki sticks from a bucket.

Wild Rover: Bar in Faneuil Hall right next to Hong Kong. Karaoke on the bottom floor, and a dance floor on the top. Radio stations often have promo parties here.


Blazing Paddles: A fun bar right on Yawkey Way near Fenway Park! The entire bottom floor is filled with ping pong tables. Everyone from the Patriots to the Bruins to the Red Sox host fundraisers here.

The Greatest Bar: Ideal for sports games. Tons of TV’s everywhere, plays music videos at night!


Harpoon Brewery: The best $5 you will ever spend. Buy tickets for a short brewery tour and have 20 minutes to try all of the free samples you can drink!


Sam Adam’s Brewery: Similar to Harpoon Brewery, great to stop in and see one of New England’s favorite beers being made!

Places to Stay

Residence Inn by Marriott Boston Harbor on Tudor Wharf. Reasonably priced, great location, you won't have a problem getting around here.


Airbnb also always a great option. Search around looking for well-reviewed apartments.


Use the MBTA, nicknamed “The T” to get anywhere you need.


Uber is another alternative that can get you around the city.


Note: Parking is very difficult to find and if you do find it, it will really cost you!


Things to Do

Plymouth Rock: Monument that shows where the pilgrims landed in Massachusetts.


Plymouth Plantation: a New England staple for immersive historical field trips. Actors dress up as pilgrims and Native Americans while showing what it was really like to live back in those times.


Martha’s Vineyard: Take the ferry over to Martha’s Vineyard and enjoy upscale food and shopping. Referred to as just “The Vineyard” by that crowd. Take a stroll, you never know what celebrities you could bump into!


Nantucket: Very similar to Martha’s Vineyard. Locals tend to go to Nantucket vs. The Vineyard, but both are still well-attended. Home of Figawi, huge race weekend for boats over the summer!


Cape Cod Melody Tent: small outdoor concert venue, great for a summer night!

Places to Eat

Crisp: Fire-grilled pizza down Cape Cod! Great atmosphere and service.

Places to Stay

The Cape Codder Resort: All places in Cape Cod are going to be on the more expensive side, so be prepared to dish a little bit of coin out if you're trying to stay. Everything is upscale and dominated by boat money, but the Codder Resort is your most affordable option!

Boston Common

Boston Common

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