Two-Day Towns: Boston

It’s a perfect Boston day at the end of another great trip—85 degrees and sunny. And what are we doing? After dropping off the rental car (we needed it to go up north), we’re dragging our luggage down what’s hard to call a “street” to Santarpio’s in a “not great” section of east Boston. Why, like normal people, are we not taking the shuttle to the airport? Too easy—and we’d miss the Santarpio’s experience.

In a way, Santarpio’s is a good analogy for Boston itself. It’s provincial, has an unapologetic accent, and, even with all the hype, still embraces its blue-collar roots.

It’s hard to call Boston a two-day town. It’s more of a series of two-day towns, all wrapped up in one city. It’s relatively small and easy to visit in two days, but what makes the city unique is the fact that each section, although close in distance to the others, is vastly different in style. Do you approach the city as a historian? A tourist on a duck boat tour? A foodie? A world traveler? As an academic? Boston can be different for all of the above.

My favorite summary of Boston was a conversation with a Boston cab driver a few years back. He picked us up from an area not far from Logan Airport, and we gave him an address near Boston Common.

“Whoa,” he said. “I don’t often go into the city.”

“Ummm, it’s less than two miles as the crow flies, about a four-mile drive.” I responded, a bit dumfounded. It was literally about a five-minute drive through the tunnel (without traffic).

“Yeahhh,” he responded, emphasis on the extra Boston-provided “h” sound that seems to make its way into every word. “That’s why I stay ovah hehh.”

Like I said, provincial.

Every neighborhood is distinctly different, very walkable, and linked to the surrounding ones. But those who live and work in the North End never go to the South End. Back Bay? Fuhgeddaboudit. And Cambridge is basically in a different state, even though you can see it clear across the Charles River.

Enough with the editorializing.

We love Boston. David (Shea) is from Boston, and has been seeing a lifetime of transition there. I’ve been going at least once or twice per year for nearly 20 years… And Boston never gets old.

You’re not going to get a rundown of the best tourist spots in the city from us, nor will you get a recitation of the best duck boat tours. But you will get a list of places that have become our favorites, along with the advice to get off your duff and walk the city.

North Square Oysters and cobbles
row 34

Around Boston Common:

Boston Common is such a great gathering spot in the city. It’s touristy and always seems crowded, even on a miserable winter day, and the combination of the Common and the Public Garden is a great green heart for Boston. It’s also fun to know that it was a common ground for raising livestock. Granted, that was in the 1600s, but it’s still pretty cool and a brilliant example of city planning.

On one end, you’ll find the State House, Granary Cemetery, Faneuil Hall, and Quincy Market. (Quincy was originally set up for Saturday markets. Even now as a tourist attraction flanked by chains, they still have a Saturday street market nearby with great street theater and a lot of “h-dominated” words.)

On the other end, by the Public Garden (with all the famous ducks in their seasonal best), sit Newbury Street, Commonwealth Avenue, and Copley Square.

Staying around the Common gives you a great central location to explore. Our favorite hotel option here is the XV Beacon. It’s a little dated, but was designed in a timeless aesthetic, so it’s forgivable. And they give you chocolate-dipped strawberries and great service. Other good hotel options are the Ames (in between Faneuil Hall and the Common) and the Liberty Hotel (at the end of Charles Street, on the tail-end of Beacon Hill). The Boxer is another reasonable choice close to the North End, but we’d say it has good proximity, but not a great location. The Four Seasons is also a close, safe, higher-end choice.

In terms of restaurants, those around the Common are the not most notable in the city, likely because rent is probably ridiculous. There are a few great options, though. No. 9 Park, a perennial favorite from Barbara Lynch, is still one of the best small, sophisticated bars for champagne and a nibble (a full dinner there is still a bit formal). Mooo, in XV Beacon is a decent steakhouse with a good bar, but the room is tired and in need of a distinctive identity. Cultivar, claiming local sourcing and seasonal cuisine, is the newest restaurant in the Ames Hotel. Haley Henry is a great newer cocktail bar that’s already one of the best little places in the city. Yvonne’s took over what was one of the most historically known restaurants in Boston (Locke Ober) with a swanky supper-club-style place.

Beacon Hill has neighborhood joints like Grotto and the Red Hat, and everyone who lives nearby will name a different favorite if you ask. Beacon Hill is one of the most fun neighborhoods to walk through, with its great housing history and crooked sidewalks, where trees are (thankfully) winning the battle over governmental improvements.

Everyone has to go to Union Oyster House, near the Faneuil Hall marketplace. It’s not the best in the city, but it’s actually good. And it’s an experience you just need to have—I think the notable sign has its own Instagram account.

modern pastry

North End:

The North End can feel immediately touristy, if only due to the sheer volume of people (thanks, Paul Revere, Old North Church, Freedom Trail, and co.), but if you’re there in quieter times, you’ll see the old Italian gents sitting on their stoops, speaking their native language. It has legit Italian roots. It also has the city’s best, and unfortunately most popular, oyster bar, Neptune Oyster.  If you can’t get in, North Square Oyster is a fine substitute; a relative newcomer with great oysters. There are a few fun places to try, like Bricco, but the fun of the North End is to wander in and out, grabbing a drink here and there, and indulging in some oysters or pizza in all of the very cool Italian-ish options. And don’t leave without cannoli. The battle between Mike’s Pastry and Modern Pastry is a serious one, but we’re Modern devotees.

After a drink at Bricco, one of our bartenders asked about our next stop. We said we were headed to try Row 34 in the Seaport area.

“Wow,” she said, want me to call you cab? “ No,” we said. “We’re walking.”

It was about one mile.

Boston is smart enough to heal the sores of the past, i.e. removing the 1950s elevated highway that separated downtown from the waterfront, via the Big Dig. The expanse of time it took was much-ridiculed, but the project was an incredible success in city progress and planning. A tunnel now sits where the highway once was; its top is home to Saturday markets, greenways, and people gathering and walking to and from the North End and waterfront into the city.

north square oyster

Seaport/Fort Point Channel:

This area transformed from a blighted port for container ships and the backwater of the city to a convention area, which is now becoming a legitimate neighborhood. It’s just across the bridge from the Harbor/Waterfront area (a short walk). It has a host of mostly chain hotels to chose from, but the most notable part is all the great restaurants including Row 34, Sportello, Blue Dragon, Drink (one of the original unique cocktail bars), Menton (Barbara Lynch’s finer-dining contrast to Sportello), and Tavern Road (a pub that’s not destination-worthy, but a decent stop if you’re in the ’hood). Even Mario Batali threw his hat in the ring here with a Babbo Pizzeria.

The Harbor Waterfront:

The Harbor/Waterfront area also has a great many tourist attractions: the ferries to the Cape, the New England Aquarium, and just the general waterfront vibe. The two big-dog hotels of note in the area are the Intercontinental and the Boston Harbor Hotel. Although the area isn’t a restaurant mecca, two great spots nearby are O Ya (an incredible sushi experience, now with a NYC outpost) and Trade. Both are a few short blocks from the small, but cool, Chinatown area, which is also worthy of a visit.

The South End:

If Commonwealth Avenue and Newbury Street make up the Back Bay, Tremont Street is the spine of the South End. The turnpike seems to be the dividing line between the two neighborhoods. Many young professionals and families started moving into the South End about 10 years ago, and it’s made for a great neighborhood with renovated brownstones and yet another of the greatest oyster bars in town, B&G Oysters. (In the same intersection as B&G, you can also choose from the Butcher Shop, B&G’s sister charcuterie/wine bar, or Aquitaine.)

In addition to B&G, South End also has SRV, which is a great Italian-inspired spot, and Myers + Chang, one of the more popular Asian places in town since it opened (probably five to seven years ago). South End also has Toro, arguably the best known place in the area. (Footnote: Even with all the hype and attention, it wasn’t our favorite. Much preferred the same chef’s more unique casual joint, Little Donkey, in Cambridge).

little donkey wall
waypoint cambridge

Cambridge and Somerville:

According to most people who know Boston, this is where all the greatest new restaurants are opening. There are a lot of great choices, but it begs the question whether it’s worth the (albeit pretty short) drive. What makes a place destination-worty? This area of Boston boasts some of the best colleges in the country, all shoehorned into a small area: Harvard, MIT, Boston University (just across the Charles River), Radcliffe (merged with Harvard)… It’s insane. Too bad Boston College (further southwest) didn’t also jump into the area. But if you want to be near enough to suck in some Ivy League air, you can stay at the Charles Hotel and walk to some of the restaurants of note.

Destination worthy? In Somerville: Juliet and Tasting Counter (if you like the long, notable tasting menus). In Cambridge: the afore-mentioned Little Donkey, Craigie on Main (which sort of put Cambridge on the restaurant map with the now-closed Hungry Mother), Loyal Nine for seafood, and Les Sablons (Island Creek’s Frenchie sister). If you’re in the ’hood, you can also check out Waypoint and Puritan & Co.

Boston 1110 015
santarpios pizza

And what about East Boston and Charlestown? Visiting these neighborhoods will definitely show you all of Boston’s dichotomies, but other than Santarpio’s and Boston Logan Airport, there’s no reason to stick around. But the people who live there love it and all have their own lists of restaurants they swear are the best in the city—but they may not tell you about them, for fear that they’ll be discovered (a la Santarpio’s).

So—about Santarpio’s. Why on earth would any pizza be worth dragging your bags a short, but pretty unpleasant, walk? Well, the first time we were there, Lefty was manning the large charcoal grill in the very front (with suspect venting—it took three days to wash the smoke out of my hair). Paulie was slinging drinks, with the most adventurous option being Coors Light. The pizza selections were limited; the meat came hot off the grill. It was old-school all the way, and one of the most memorable meals in a long list of worldwide dinners. In the age of tasting menus, foam, tweezers, and celebrity chefs, it was like a breath of (albeit smoke-filled) fresh air.