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Your post appears to be one of a number of commonly asked questions about the port city of Boston. Please check the sidebar for visitor information. Ah Hi! Ive always wanted to respond to one of these, but I normally reach the post a few hours too late. I'll do my best to give you some good recommendations. So first things first, Boston is VERY walkable and easy to get around, especially if you take the T (what we call our subway). People on this subreddit love to shit on the T (and everything else honestly, very pessimistic group of people), but in actuality its great, especially by American standards. I would consider getting a day pass so you can ride it as much as you want, but I am not sure how much they cost/if it would be worth your while (a single ride is around $2.75 I believe?? Not really sure). With that being said, I would say one of the first places you should check out is the North End. It is a very Italian American neighborhood, and has a pretty strong European-esque feel to it. There are great Italian restaurants and shops everywhere. The touristy thing to do is to go to Mikes Pastry's for cannolis, but I (and I think most locals would agree) recommend Bovas instead. The whole neighborhood is super compact and dense, and it will be mad easy for you guys to walk around and check it out. Nearby the North End is Faniuel Hall/Quincy Market, which is probably the epicenter of Bostons historical/tourist scene. The food there might be a bit overpriced/overhyped, but I personally have to recommend the Boston Chipyard. Its a stand within Quincy Market that sells fresh, mini cookies. Ive been living here for five years (and visiting my entire life) and I STILL always go there whenever I am feeling sad and need a pick me up/just craving a cookie. I love it and its absolutely delicious. Id also suggest just strolling around Beacon Hill and the Back Bay neighborhood (particularly Commonwealth Avenue). The architecture there is beautiful, and both are very serene and picturesque, and really just great places to walk around and soak in the ambiance. Both neighborhoods have plenty of bars/restaurants/shops, so youll have plenty of other things to do besides walk around. They are super close to one another, and very conveniently located right in the heart of the city. Also gotta check out the Esplanade, its a cool park right along the Charles River, its super pretty and relaxing, and also right next to Back Bay/Beacon Hill, so really convenient to get to. One of my favorite places in the city. In terms of less touristy things to do, Id suggest going to the Arnold Arboretum in Jamaica Plain. Its basically one giant park/tree zoo, and its filled with really beautiful trees and plants, and is just a lovely place to walk around. This is definitely one of the cooler places in Boston, and definitely not something that the average tourist does. Its right at the end of the Orange Line (Forrest Hills), so while it is kinda far out compared to the other places I have mentioned, it really is not that hard/complicated to get to. Great place to just vibe out and relax, and its one of my favorite places in the whole city. Obviously Boston/New England is known for its seafood, and it really is tremendous. There is a lot of debate about which place has the best clam chowder/lobster roll, and it ultimately comes down to preference, but I always recommend to visitors the Barking Crab. It is located right on the water in Bostons Seaport neighborhood, so again, very centrally located. I think the food there is delicious, and I think it offers the best ambience/overall dining experience. It does a good job of kinda replicating the traditional New England seafood shack, while still being more of a legit restaurant. Again, some people may shit on me for that answer, but at the end of the day, if you go, youre gonna have a good time/delicious meal. Other quintessential Boston things are the Freedom trail, Duck Boat Tour, harbor walk, and visiting Fenway (which it seems like you are already doing, although i highly recommend going to a game if you can, not sure if the Sox are in town this weekend). Cambridge is located right across the Charles River from Boston, and while it technically is its own city, it feels like it might as well be an extension of Boston. Both Central and Harvard squares are a lot of fun, with plenty of cool restaurants and stores to check out. One last non-touristy thing I recommend is visiting East Boston, or Eastie. Its really easy to get to on the Blue Line, and is just a really underrated neighborhood as a whole, and definitely is not the type of place a tourist would usually go to. It has some beautiful parks right on the water that have great views, as well as many really good Latin food spots. There is the ICA watershed, which is a really cool contemporary art museum located right in the Boston Shipyard. Also, there is an Australian meatpie place right there called KO Pies that my friends and I always go to when we are in the area. For all I know, it might not even hold a candle compared to the meatpie places you have back home, but the people working there will definitely get a kick out of serving a fellow Aussie. All in all, Boston is an incredible place with a unique sense of charm and distinct identity, and it takes a lot of pride in itself, which I love. It does a great job of blending the big city/small town feels, and in my opinion, is the best city on the East Coast. Please feel free to message me if you want any more specific recommendations. Enjoy your visit!!

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also keep in mind it's Halloween weekend so it's probably going to be even busier than usual

Seaports not bad spot if you have one night. Not going to give you a “true Boston experience” but you have plenty of restaurants, a brewery (trillium), and I think they just opened some indoor mini golf bar down there too.

If you’re looking for another neighborhood that might give you more “Boston” vibes the south end has a ton of amazing restaurants, you could also catch some live music at the beehive or Daryl’s.

Last spot I’d suggest is fenway. There’s plenty of bars there, outdoor beer garden, and a giant food hall. 30 year olds might feel, well old, depending on where you go.