Zen Restaurant
Zen is a relatively recent addition to the dining scene on Beacon Hill. Most things in this part of town tend toward the small grill or sandwich shop so it's nice to have something cultural as an alternative.
Zen's sushi seems a cut above the kind of sushi that you'd be able to pick up at Whole Foods though it's not top of the line either. Their take on other traditional Japanese fare (miso soup, soba noodle dishes) is nothing outstanding. Prices aren't ridiculous but it's not an inexpensive meal out either.
Titus Sparrow Park
Titus Sparrow Park is a genuine meeting ground for families in the South End. In a city where class and race divisions can be so pronounced, people really come together at this park. There is ample green space for kids to run and play and two playground sections, one for toddlers and one for older kids. The sandbox is the big draw bringing parents out early in the mornings and well into the evenings. Parents who come to this park are genuinely friendly and very interested in meeting other people.
In the summers, the park has a jazz concert series on Wednesday evenings making it a great place to pick up dinner and have an evening picnic.
Emmetts
If you watched the early years of "The Practice" this was the place that the cast frequented on the show (before it was Emmetts). Given that it is an Irish pub there aren't that many standouts food-wise. They do a decent job on traditional stuff. The draw here is that its got good beers and that it's a downtown watering hole. Stop in during the NCAA basketball tournament to keep current during lunch.
The staff are fairly friendly but warm up to you over time if they recognize your face after a few visits.
Silvertone Bar & Grill
Silvertone is a basement bar and restaurant in the heart of downtown Boston. Just up from Downtown Crossing, you'd miss it if you were walking quickly up Bromfield.
Something about descending down into the bar gives it a sort of speakeasy, loungy feel, and the retro vibe makes for great atmosphere. It's also kind of cool to be able to see the place from above as you go in. Because it's a basement there are no windows but it doesn't feel cramped. It's well lit and the smoking ban helps quite a bit.
The calamari appetizer is particularly good, and so is the grilled cheese, and the mac and cheese. It gets pretty crowded pretty quick but it's easy to chill there.
Motley Home
I'm a big fan of Motley (pretty much across the street) and I thought I would automatically love Motley Home, but it seems they've got a fair amount of stuff that you just don't need. The original Motley has this fun vibe of hip shirts, books, and jeans but the home store seems like a bunch of stuff just heaped together.
The view from the street is enticing but being inside doesn't quite deliver. You might as well just head to Urban Outfitters.
Boston Public Library - South End
With the main branch of the library a few short blocks away, it can be forgiven that the South End branch is fairly small. Though it occupies two floors with a fairly large footprint on Tremont Street, almost the entire top floor is community meeting space. That leaves precious little space for books and other materials.
The library tends to be loud during the day which makes it more of a place to browse for things and take them with you rather than stay and do reading.
The connection to the Internet, while free, is particularly flaky so bringing your own PC won't get you much as far as WiFi connectivity goes.
The library does a fair trade in movie "rentals" which was a bit of a surprise. And their children's book selection is quite extensive. We tend to browse in Borders nearby then reserve the books online for pickup at the branch.
Encore
Encore has become the de facto place that my family stays when they visit Boston. Staying in an urban b&b gives you a totally different take on the city and Encore is very tastefully appointed. It is right in the heart of the South End with lots of small and independent retailers, and there is a mall nearby too. It's not far from public transportation either.
Reinhold the host is is especially friendly and accommodating.
Tannery
This place can be hit or miss, very often on the miss end. The sales team tends to be a bit high pressure and they aren't all that friendly to people who bring their children in while shopping. Especially if you have a stroller (they think we should just stay home?). If you've seen the shoe you want and are comparison shopping on price then it may be worth going. But it's not a great place to get good customer service and a pleasant shopping experience.
Yale Appliance
Kind of out there on its own away from the malls and the other big box stores, Yale Appliance is a destination. You can go with purchasing a dishwasher in mind but can have lunch, watch a show or two, and spend time browsing with the super-friendly, and super-helpful staff.
We needed to order appliances for some oddly-shaped spaces during a kitchen renovation and their staff was very helpful in finding the right sizes and models to fit the spaces. We also had a series of mishaps with a refrigerator door being damaged on delivery (it took three tries -- the logistics of the global economy) and each time they took back the damaged part no question. They also meet other advertised prices so there is no concern that you'll find a better deal somewhere else. It's worth the trip out.
Miriam and Sidney Stoneman Playground
As we travel more with a family we realize the importance of knowing where the fun pit stops are for kids (and maybe a rest for adults). The Stoneman playground has a fantastic view of the water and the Cambridge/MIT skyline. The park itself is split perfectly into toddler and older-kids' play areas with lots of soft landing spots that encourage climbing, jumping, and running. This a great place to stop if you've been visiting Harvard or MIT or the Science Museum. From here it is a short walk into the Back Bay for lunch and shopping.