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Beka’s guide to Boston. Feel free to add to this!
Overview
Boston is a fabulous city with lots of great restaurants, tons of history, a vibrant sports scene (if that’s your thing), and good public transportation. It’s also a very small city geographically, so it’s really easy to get around, and especially walk through.
Price guide:
- $ = under $10 per person
- $$ = about $10-25 per person
- $$$ = about $25-40 per person
- $$$$ = over $40 per person
Arriving / Getting Around
Boston provides free transportation from Boston Logan (BOS) into the city if you arrive by plane. Follow signs for ground transportation at the airport, as you’ll want to take the silver line MBTA / bus into the city. You can also take the MBTA blue line into the city (Bostonians just say, “The T”).
The silver line will take you to South Station (~20min ride), which is right near the financial district downtown, and this makes it easy to get pretty much anywhere.
Boston is the most walkable city I’ve ever been to. You can walk pretty much anywhere downtown, from the North End to Back Bay. You could even walk to Fenway, though it’s a longer walk at about 2 miles. The T is ~$2.65 per fare, and gets you anywhere further easily.
Uber is typically safe, fast, and cheap, but sometimes drivers aren’t from the city. It’s best to leave it for longer trips — no point if it’s under a mile or so. Take the T or walk.
The silver line bus returns to the airport, but this time you pay the T fare to return to the airport. It’s faster and easier (and way cheaper) than an Uber because it has a dedicate route, so pretty much no traffic. Purchase a one way adult ticket from any kiosk in South Station, and follow the signs for red / silver line to take the silver line bus back.
Where to stay
Boston is not a cheap city to stay in. Hotels are typically $150 to $300 per night, and good AirBNBs are at the low end of that range. My favorite places to stay are:
- Hotel: Boston Park Plaza — centrally located, reasonably priced (they also typically run specials or packages at like $140-199), and easy to get anywhere. It’s nice but just a bit older, and wifi is ~$10 per day.
- AirBNB: staying near the theatre district is usually a great bet, as it’s between the north part of the city (financial district, Quincy market / Faneuil hall, North End), and the south part (Boston Common park, Back Bay, Beacon Hill). There’s one at 8 Winter Street right in Downtown Crossing that’s run by a relocation company that was great (~$179 / night).
Restaurants
I’m going to do these in alphabetical order, but I have to list my absolute favorite place in the world first: Rino’s place ($$-$$$) in East Boston. To be blunt, East Boston is a dump. This place is a hole-in-the-wall with about 12 tables and amazing Italian food. Homemade pasta made each day, great food and seafood, but long lines. Skip Giacomo’s in the North End, that place is crap compared to this.
Tips: Go for a “linner” at like 3:30p – 4p in between lunch and dinner as they start serving dinner (take a car, you can take the blue line T back). Otherwise you might have to wait a couple hours, as there’s no reservations unless your party is 6 or more. Pretty much everything on the menu is great, and if it doesn’t come with homemade pasta, you can get it for a couple bucks more (worth it). My least favorite thing is the chicken parm; favorites: lobster ravioli, open ravioli, veal saltimbocca w/ homemade pappardelli, matriciana (homemade rigatoni!), the bolognese. Start with the fried mozzarella or calamari.
Now on to the rest:
- Al’s ($), Leather / financial District, but multiple locations: A Boston lunch staple. In true financial district fashion, it closes at 3pm every day. The meatball subs are pretty amazing — there’s a dedicated line for just meatball subs at lunch.
- Atlantic Fish Company ($$$), Back Bay: Some of the best New England clam chowder around and excellent fish (sort of a Ruth’s Chris of seafood). The have set menu items, or you can pick one of several fresh fish (rotates like a ‘catch of the day’), along with how you want it cooked. The Ahi Tuna is superb.
- Boloco ($), Multiple locations: Like Chipotle, but more options and ordering on an iPad. Good for quick bites, very good breakfast bowls.
- Gourmet Dumpling House ($-$$), Chinatown: Soup Dumplings — pork and crab. You’re welcome. Also good lo mein and sesame chicken.
- James Hook ($-$$), Financial District: Right on the water on Atlantic avenue, there are two great things here: clam chowder and lobster rolls — the no-nonsense kind that are pretty much just lightly toasted rolls, butter, and a whole lot of lobster.
- Legal Test Kitchen ($$), Seaport: Regular Legal Seafoods — not really worth it. Test kitchen? Very cool menu and some interesting dishes (not just seafood). If they’re doing the seafood paella, it’s great.
- Post 390 ($$), Copley: My personal favorite clam chowder in the city. Great for lunch, as their take on a BLTA is really good, and solid burgers as well. They also do a great brunch on Sundays.
- Stephanie’s on Newbury ($$$), Back Bay: Interesting comfort food like lobster guacamole — “classier comfort food” if there is such a thing. There’s also one on Tremont.
- Sweet Cheeks ($$), Fenway area: Biscuits you would club a seal for. Amazing Texas-style BBQ. The pork belly, briskets, collard greens, and black eyed peas are superb. Oh, and the most amazing fried chicken I’ve ever tasted (and my mom grew up in the south!).
- Top of the Hub ( $$$-$$$$), Back Bay: The best view in the city — dinner at the top of Prudential tower. Lobster, filet, and all your classier stuff, with a jazz lounge as well (Prudential lounge).
- Union Oyster House ($$-$$$), Fanuiel Hall: The oldest restaurant in the US or something. Great oysters, clam chowder, seafood — and JFK’s favorite. If you make reservations early, you can sit in his booth.
There are food trucks around lunch time, and The Dining Car is a great one. The Korean BBQ sliders are a favorite on the summer menu, but the lamb + black bean chili for fall / winter is on point. The food truck with the brick oven pizza is the best pizza in Boston. Related: Boston pizza sucks, not worth it overall. Go to New York.
A lot of tourists will hang out here Quincy Market ($) in the Faneuil hall area. It’s pretty much a tourist trap and not worth it — there are a couple good seafood / lobster mac n cheese places, and Boston Chowda Co isn’t bad, but otherwise you can skip eating in this mad house. Oh and the Cheers bar here is fake, but it looks like the set. The real Cheers bar is down the street from the MA state house, but they only filmed external shots there.
Bars
- Drink ($$), Seaport: A bit pricier as drinks go, but a very cool place & great vibe. They don’t go over capacity so there might be a wait, but it makes for a better experience. No cocktail menu, just really awesome bartenders — tell them what kind of drinks you like, and they’ll make something special for you. Really neat.
- Frost ($$$), Faneuil Hall: Basically a novelty, but pretty cool. There’s like a $12 cover or something, and the drinks aren’t cheap, but the entire bar (including your glass) is made of ice (you get a parka / gloves to go in). Fun way to waste an hour
- Mr. Dooley’s ($): A pretty traditional Irish pub near Faneuil hall / North end. Live music some nights, good bar food and beer.
- Paddy O’s ($): Another traditional Irish bar owned by the same people as Mr. Dooley’s. Not a bad place to start a crawl between this, Hennessy’s (you guessed it, Irish pub), and The Bell in Hand (the oldest tavern in the US).
- Prudential Lounge ($$), Back Bay: 50-some floors up at the top of Prudential tower. Jazz lounge and a great compliment to Top of the Hub if you do it.
Coffee / Dessert
Hands down, Flat Black coffee is the best. It’s in the financial district, so weekdays only until 5pm, but run by coffee-snooty Aussies 
Otherwise, there’s like a Dunkin or Starbucks on every.single.corner.
For dessert, the North End has Mike’s Pastry and Modern Pastry ($, cash only) right near each other on Hanover street — staples for a cannoli or other Italian pastry. I like the filling at Modern and shells at Mike’s, but worth trying both.
Toscanini’s near MIT is supposed to be the best ice cream in the country. It’s overrated (Salt & Straw in Portland is better), but it’s very good and has some interesting flavors if you’re willing to take a car / T out there.
Stuff To Do
- Freedom Trail (free): This starts in Boston Common, which is one of Boston’s several fabulous parks. Download an audio tour / podcast from iTunes or pay for a guided tour. Takes you through historical sites in Boston, such as Sam Adam’s and John Hancock’s graves, where Paul Revere planned his ride (not to mention it goes past his house), and lots of other cool sights. If you walk the entire way out to the USS Constitution, you will be tired.
- Duckboat tour ($35): A bit pricey and you probably need a reservation, but you learn a ton about the city and you get you drive on both the streets and out on the water, so pretty neat.
- Harpoon Brewery ($5): Out in Seaport (take a car), this is a pretty good brewery tour that lets you try every beer they have at that time, maybe some green beer, and they have great soft pretzels to buy.
- Sam Adams Brewery (free): The Sam Adams tour is probably better than Harpoon, but it takes a lot longer to get there. You can take the T though — just get there early in the morning.
- The Esplanade (free): Take a walk on the Charles River on the west side of downtown (between downtown and Cambridge). Have a picnic or something.
- Universities: Take a walking tour of Harvard or MIT if you want to venture over into Cambridge (red line on the T). Get smarter by osmosis.
- Red Sox ($40+): Nothing is really more quintessentially Bostonian then a Sox game at Fenway. Game days are a great experience, and there are lots of bars / restaurants around the park. It’s easy to get to by taking the green line to Kenmore Square (you don’t have to go to the Fenway stop) — just follow everyone else and the game day signs off the train. Cheap tickets are ~$40, so it’s not a cheap park.
If you want the “lite” experience, you can check out the Bleacher Bar in right field, which is usually pretty busy on game days, but is located in right field so you can get a look into the park on game day. Also a great pre-game place.
- You’ve also got the Bruins and Celtics to check out, depending on the season in TD Garden (also in the city).