Two Days in Boston

[UConnDad]

I live and work here and people ask me all the time what should we do when in Boston. And I always laugh because I'm here everyday and can't think of cool stuff to do since I don't think about what it's like to be a tourist here. I think of Boston in neighborhoods. Neighborhoods you want to check out are Back Bay, Beacon Hill, North End and South End. South Boston also if you have time. Try to do something in each of these neighborhoods. Boston is pretty small so it's easy to walk everywhere or take 5-10 minute Uber rides.

Touristy things - Besides things already mentioned I always thought the Duck Tour was kind of cool. Easy to way to see the entire city in a few hours. Leaves from Back Bay (Prudential Center), downtown (at the New England Aquarium) or Cambridge (at Museum of Science).

Beer - Trillium has great beer but instead of going to the brewery in the Seaport go to the Trillium Beer Garden on the Greenway downtown. Closed Monday and Tuesday so probably won't work for you. Close to North End so you can combine that with a beer or two before or after dinner in the North End. The Trillium brewery in the Seaport is also fun and that is open everyday (and serves lunch and dinner).

Food - Here are some options in different neighborhoods.
North End - There are so many good ones. Lots have outdoor seating if it's nice out. Arya Trattoria is very good but it's on the 2nd floor so no outside seating. Carmelina's is good also and has an outside seating area. Get a cannoli at Mike's or Modern Pastry. Both on Hanover Street and both always packed. If you like pizza walk over to Regina Pizzeria at 11 1/2 Thacher Street. Known as the best pizza in Boston.
South End - SRV is one of my favorites. Then walk over to the South End Buttery for dessert and sit outside on the bench and people watch.
Back Bay - Stephanie's has good, not great, food but the outdoor deck is the best people watching place. On Newbury Street. Grill 23 for steaks (expensive).
Beacon Hill - Peregrine and Scampo are both very good if you want to check out this area. Grab an ice cream at J.P. Licks and then walk down Charles Street, the most authentic old Boston retail street in the city. No chains here.
South Boston - I like Fox and the Knife. Kind of a hard neighborhood to get to from where you're staying. Too far to walk. Broadway T stop on the red line is right across the street from this restaurant.

We love the Fort Point Trillium but if the weather cooperates the beer garden looks great. Good beers especially their porters and stout. Also in Fort Point is a restaurant called Lolita that we like.

 

[Umami Zen]

Nothing wrong with this, but aren’t both Legal Sea Foods and Capital Grille chains?

They are. .Legal started out of Boston.. Plenty of steak houses in Boston.. And yes--CG is a chain.. If you like wine with your beef.. Grill 23 is hard to beat but there are plenty of choices..

 

[8893]

Have a couple dozen excellent oysters and the best fried calamari of your life at B&G Oysters in the South End, and then walk across the street to the Butcher Shop for dinner. Both are Barbara Lynch restaurants.

That's what we did for my birthday in 2021. Both really great; and definitely some of the best oysters I've ever had,

 

[brasssbonanzaa]

Neptune's in the North End is off the charts.. .. Gotta get there early..5:30-6.. You won't be disappointed.. Even Boston folks don't know about it..

The last sentence couldn't be further from the truth - everyone in this city knows about Neptune Oyster. We just don't bother going there to wait in line for 4-5 hours.

 

[gsmooth]

Thanks everyone! I think most of our attention will be on the North End (I don’t think I’ve been there since I was 10) after we drive straight from home to the Institute of Contemporary Art.

After checkout we’ll probably drive to another neighborhood before hitting a dispensary and then driving home.

Looks like beautiful weather for Monday and Tuesday: no rain and weather no warmer than 75.

I live here in the Boston as well, and just like HooperScooper said, it takes me a while to think about it because I am not in a tourist mindset. If you do have time, Harvard Square is a nice place to walk around during the day and you can rent some bikes and ride along the trails besides the Charles River and Memorial Drive and the Massachusetts Avenue bridge that connects Boston with Cambridge. This will get you some nice snapshots to take.

I concur with what a poster said above, if you are in the Copley Area, Atlantic Fish and Co is better than Legal Seafood's.

If you are going to the North End, then Modern Pastry is a nice dessert place.

 

[Jay-Bone]

The last sentence couldn't be further from the truth - everyone in this city knows about Neptune Oyster. We just don't bother going there to wait in line for 4-5 hours.

The one time I walked in during a 12" snow storm my little necks were in a cheese whiz broth. Being the only customers in Mike's afterwards was kind of cool though.

 

[Umami Zen]

The last sentence couldn't be further from the truth - everyone in this city knows about Neptune Oyster. We just don't bother going there to wait in line for 4-5 hours.

Kinda like what Yogi Berra used to say.. No one goes there anymore because its too crowded.

Worked in Boston for 20+ yrs.. Many of my co-workers who were natives had never heard of Neptunes

 

[HuskyHawk]

With the Iceland trip officially postponed, we're driving up to Boston on Monday to spend a night at The Boxer, which is on the western border of Bulfinch.

It's my first time in Boston in years and most of my time spent up in Boston was in Allston and Cambridge.

We spent a bit more money to stay in the city proper so we can walk to all attractions.

What are the "must dos" for about 30ish hours in Boston?

Lots of good suggestions. Freedom trail is always good and will lead you through the North End and to the Constitution in Charlestown. I think the North End is overrated, not much there but Italian food and Mike’s pastries. Nothing that isn’t also present in NYC except the Old North Church. But for me history >> food. Gardner Museum is really cool, and gorgeous inside. The Warren Tavern in Charlestown is a nice lunch spot with some history.

The Seaport is worth checking out just because it’s new and different. Trillium is there plus two other outdoor beer garden places. Lots of restaurants directly on the water. No shows at Leader Bank Pavilion until Wednesday unfortunately.

The Red Sox are home the next two nights and even if you don’t go, the Fenway area is fun when there are games. There’s a Trillium location near Fenway now too.

 

[CL82]

A lot of good advice in this thread. Let me second the Constitution. That ship with its live oak and shallow draft was a huge technological jump and lead to standing British orders that no single ship of like class be allowed to take her on alone. She was faster than ships that had the equivalent fire power and could outgun British ships that could keep up with her. She holds a remarkable place in history.

A second the duck tour as well. Those are always fun and the one in Boston is no exception.

 

[Waquoit]

If you do art museums, the MFA has a major J.M.W. Turner exhibition going on. We're going next week. Closed Tuesday, though.

 

[dvegas]

If you are driving up via 84, BT's smokehouse in Sturbridge is a great "rest area" for a yummy snack or meal. If you are into Greens, Heal dispensary a mile west of BT's is better and cheaper than any recreational shop in the Boston area.

 

[HooperScooper]

If you are driving up via 84, BT's smokehouse in Sturbridge is a great "rest area" for a yummy snack or meal. If you are into Greens, Heal dispensary a mile west of BT's is better and cheaper than any recreational shop in the Boston area.

And if you're going to those 2 places then you might as well go to Tree House also.

 

[dvegas]

And if you're going to those 2 places then you might as well go to Tree House also.

I'm a hard liquor guy over beer. My 3rd stop in Sturbridge is Yankee Spirits, a favorite of mine and my dorm/housemates since the mid -1980's at UConn. A superstore before there were any in CT. Nothing special in the beer/wine area, but most handles are $5-$10 cheaper than here.

 

[Edward Sargent]

Thanks everyone! I think most of our attention will be on the North End (I don’t think I’ve been there since I was 10) after we drive straight from home to the Institute of Contemporary Art.

After checkout we’ll probably drive to another neighborhood before hitting a dispensary and then driving home.

Looks like beautiful weather for Monday and Tuesday: no rain and weather no warmer than 75.

We stayed at the Boxer for Paul Simon concert at the Garden. Nice place with great access to North End and Seaport. ICA is interesting but we liked Isabelle Stewart Gardner better. Legal Test Kitchen in Seaport is good too but there are too many good places in the North End

 

[6xChamps]

Thanks everyone! I think most of our attention will be on the North End (I don’t think I’ve been there since I was 10) after we drive straight from home to the Institute of Contemporary Art.

After checkout we’ll probably drive to another neighborhood before hitting a dispensary and then driving home.

Looks like beautiful weather for Monday and Tuesday: no rain and weather no warmer than 75.

FYI Ascend is the biggest dispensary on the east coast and you’re staying a block away. Other good stuff to do in the neighborhood are Hub Hall for food and Alcove/Night Shift for an outdoor drink/food. Good for sunset.

 

[HooperScooper]

FYI Ascend is the biggest dispensary on the east coast and you’re staying a block away. Other good stuff to do in the neighborhood are Hub Hall for food and Alcove/Night Shift for an outdoor drink/food. Good for sunset.

There's another new food hall downtown that is supposed to be great. I haven't been there yet but heard good things.

High Street Place - Food Hall by South Station & Downtown Boston

Explore the best of Boston's food and beverage scene at Downtown Boston's culinary destination, featuring over 20 local eateries and bars.

www.highstreetplace.com

 

[auror]

There's another new food hall downtown that is supposed to be great. I haven't been there yet but heard good things.

High Street Place - Food Hall by South Station & Downtown Boston

Explore the best of Boston's food and beverage scene at Downtown Boston's culinary destination, featuring over 20 local eateries and bars.

www.highstreetplace.com

Yeah a couple of the places in there are from Tiffany Faison (former top chef finalist, owner of Sweet Cheeks, Orfano, and Tiger Mama)

 

[superjohn]

Lots of good suggestions. Freedom trail is always good and will lead you through the North End and to the Constitution in Charlestown. I think the North End is overrated, not much there but Italian food and Mike’s pastries. Nothing that isn’t also present in NYC except the Old North Church. But for me history >> food. Gardner Museum is really cool, and gorgeous inside. The Warren Tavern in Charlestown is a nice lunch spot with some history.

The Seaport is worth checking out just because it’s new and different. Trillium is there plus two other outdoor beer garden places. Lots of restaurants directly on the water. No shows at Leader Bank Pavilion until Wednesday unfortunately.

The Red Sox are home the next two nights and even if you don’t go, the Fenway area is fun when there are games. There’s a Trillium location near Fenway now too.

I stayed in the Seaport 4 summers ago and didn't like it at all, nobody else I talked to in Boston liked it either. A lot of blocky big box stores with overpriced chain type places, had a total mall feel. Maybe it's gotten better with some age. Luckily it's a small city so only had to really rest my head there for bed.

 

[Rocktheworld]

I lived in Boston 3 years. East Cambridge, then Beacon Hill, then Bay village by the South End.

For one day/night for someone who hasn’t been in a long long time, I would split time between the north end and Charlestown. Do the latter during the morning and get a good view at the city; there’s a solid spot that at least used to be called Pier 6 on the water there. Navy yard is cool to walk through. Some good chill towny bars along the main drag. Then walk back into the city proper and right over to the north end. A lot has been built up at the Garden and that North Station area, which you’ll pass along said walk.

It’s not the most Bostonian stuff to do but if you want to pack in as much as you can into a day and a half that’s what I would do for recommendations for first time in town. You said you lived in Cambridge, as I did; another good idea would be to just take a tour along the red line lol get out and do something at each stop

 

[HooperScooper]

I stayed in the Seaport 4 summers ago and didn't like it at all, nobody else I talked to in Boston liked it either. A lot of blocky big box stores with overpriced chain type places, had a total mall feel. Maybe it's gotten better with some age. Luckily it's a small city so only had to really rest my head there for bed.

I'm not a big fan of the Seaport either but what "blocky big box stores" do you remember? There are chain restaurants down there but there aren't any big box stores that I can think of. The Seaport is mostly office and lab buildings with some expensive condo buildings sprinkled in. It grew so quickly that the city did a poor job of creating public places and a sense of place. Besides Boston Harbor being there it's a pretty blah place.

 

[auror]

I'm not a big fan of the Seaport either but what "blocky big box stores" do you remember? There are chain restaurants down there but there aren't any big box stores that I can think of. The Seaport is mostly office and lab buildings with some expensive condo buildings sprinkled in. It grew so quickly that the city did a poor job of creating public places and a sense of place. Besides Boston Harbor being there it's a pretty blah place.

Yeah it's definitely blocky, but less big box, more big hotels and offices, mixed with rehabbed wharf buildings.

 

[HuskyHawk]

I'm not a big fan of the Seaport either but what "blocky big box stores" do you remember? There are chain restaurants down there but there aren't any big box stores that I can think of. The Seaport is mostly office and lab buildings with some expensive condo buildings sprinkled in. It grew so quickly that the city did a poor job of creating public places and a sense of place. Besides Boston Harbor being there it's a pretty blah place.

Yeah it's definitely blocky, but less big box, more big hotels and offices, mixed with rehabbed wharf buildings.

Yeah, not sure what he means by big box. Ironically, @superjohn it reminds me of parts of Chicago, and yes it has changed dramatically in the last 2-3 years. It's certainly modern and includes lots of chain restaurants (but not all and most are local chains) from the World Trade north-west until you hit the brick buildings of the leather district. That's because none of it existed even 5-6 years ago except for the Moakley courthouse (and it's still pretty new). So yes, it is lacking in traditional character. South-east of the World Trade you've got an excellent concert venue, Harpoon brewery, some genuine commercial fishing piers, the cruise terminal, a cargo container port and then Castle Island. It's a bit more gritty and authentic. The leather district has character though. Lucky's Lounge is still there, a blues and jazz club that opened when I lived in Southie, so around 2001. It was the only thing there at the time.

Seaport is just branding. The whole area is "Southie" with whatever connotations that carries for people.

 

[auror]

Yeah, not sure what he means by big box. Ironically, @superjohn it reminds me of parts of Chicago, and yes it has changed dramatically in the last 2-3 years. It's certainly modern and includes lots of chain restaurants (but not all and most are local chains) from the World Trade north-west until you hit the brick buildings of the leather district. That's because none of it existed even 5-6 years ago except for the Moakley courthouse (and it's still pretty new). So yes, it is lacking in traditional character. South-east of the World Trade you've got an excellent concert venue, Harpoon brewery, some genuine commercial fishing piers, the cruise terminal, a cargo container port and then Castle Island. It's a bit more gritty and authentic. The leather district has character though. Lucky's Lounge is still there, a blues and jazz club that opened when I lived in Southie, so around 2001. It was the only thing there at the time.

Seaport is just branding. The whole area is "Southie" with whatever connotations that carries for people.

I ate at Chickadee the other night, pretty good. Probably the best spot in the Seaport as far as trendy Chef-y cuisine goes.

Chickpea fries with harissa aoili, tomato tarts, stracciatella frybread, green garlic clam pasta, and lamb porchetta. Cocktail made with peas. You get the idea.

 

[HooperScooper]

Yeah, not sure what he means by big box. Ironically, @superjohn it reminds me of parts of Chicago, and yes it has changed dramatically in the last 2-3 years. It's certainly modern and includes lots of chain restaurants (but not all and most are local chains) from the World Trade north-west until you hit the brick buildings of the leather district. That's because none of it existed even 5-6 years ago except for the Moakley courthouse (and it's still pretty new). So yes, it is lacking in traditional character. South-east of the World Trade you've got an excellent concert venue, Harpoon brewery, some genuine commercial fishing piers, the cruise terminal, a cargo container port and then Castle Island. It's a bit more gritty and authentic. The leather district has character though. Lucky's Lounge is still there, a blues and jazz club that opened when I lived in Southie, so around 2001. It was the only thing there at the time.

Seaport is just branding. The whole area is "Southie" with whatever connotations that carries for people.

Southie to me is 3 parts (maybe more). You have the Seaport area, which is all new towers built in the last few years up and down Northern Avenue and Seaport Blvd. Lacks character.

Then you have the Fort Point area next to that with all the old industrial brick buildings up and down Congress and Summer Streets that have been renovated to office use. That used to be kind seedy but now is a trendy tech area.

Then you have some old industrial areas and the Convention Center before you get to the residential neighborhoods all around West Broadway (Whitey Bulger's old haunting grounds) from the Broadway T stop all the way out to Castle Island.

Together that's most of South Boston.

 

[superjohn]

I'm not a big fan of the Seaport either but what "blocky big box stores" do you remember? There are chain restaurants down there but there aren't any big box stores that I can think of. The Seaport is mostly office and lab buildings with some expensive condo buildings sprinkled in. It grew so quickly that the city did a poor job of creating public places and a sense of place. Besides Boston Harbor being there it's a pretty blah place.

I stayed at Yotel, all the buildings across the street were ugly new blocks, I assumed they were big box stores (I'm wrong.) Granted I didn't spend much time in the Seaport because it didn't feel like a neighborhood. Only places I remember going to there was the hotel roof bar when I arrived, even the bartender told us to only have a drink with him and to leave the Seaport to have a good time. Pastorale and the Barking Crab were the only other places I went to. Wasn't a fun start to the trip, I took multiple ubers to go out for breakfast my first morning and was shut out of every single place. Driver told me every white person in Boston goes brunching. Ended up waiting outside the Barking Crab for them to open.