Shipping Up to Boston: Where to Play, Eat, and Stay in New England’s Most Iconic City

Boston skyline

Boston offers more history per square mile than any city in America. (Sorry, Philadelphia. At least you’ll always have Rocky.)

Add to that copious amounts of charm, century-old pubs, some of the country’s greatest sports franchises, and a revolutionary, in-your-face attitude that prevails to this day, and you’ve got one hell of a destination city for travelers. Here’s a definitive guide to best places to stay and the best things to do in Boston.

MUST-DO

Start at the Beginning

Boston Freedom Trail

The city’s long and storied past means history buffs might find it difficult to know just where to begin. It may seem touristy, but walking The Freedom Trail is one of the best things to do in Boston for few reasons. First, the 2.5-mile brick-lined path is the most concise route to literally walk the city’s entire historical timeline (including Old North Church, Bunker Hill Monument, and the site of the Boston Massacre). Self-guided audio tours are available for those who prefer to go it alone, or opt for a guided tour which provides a far more in-depth appreciation of the city’s Colonial influences. For first-timers to the city, the Trail also offers a great overview to orient you for subsequent travel days.

Shop Smart

The history, the scale, the sheer number of shops, restaurants, and stores. Boston can feel overwhelming. So, it pays to know where to shop smart. First up: head to the South End where you’ll find Bobby from Boston. This is a high-end outlet disguised as a thrift shop with a killer selection of one-of-a-kind vintage men’s (and some women’s) goods. We’re talking period clothing and accessories from the Victorian era up through the 1960s.

bodega boston

Fashion-forward travelers won’t want to miss Bodega. Thanks to the internet, this once under-the-radar outlet may have lost some of its underground cool. But it’s still a unique, trendsetting shoe store hidden behind a fake Snapple machine inside an otherwise innocuous corner store. Even if you’re not into footwear, it’s worth a visit just for the (bizarre) experience.

Eat Up

Narrowing down your dinner selection is a bit like having to pick your favorite bourbon (can’t you just have them all?). A solid, if obvious, place to start is the North End. It’s been continuously inhabited since 1630, making it the oldest residential community in the country. It also boasts about as many restaurants as you’d expect a near-400-year-old neighborhood to have.

Regina’s Pizzeria

Virtually every single one is Italian (or Italian-inspired), family-owned, and out-of-this-world good. Regina’s Pizzeria is one of the city’s most popular mainstays and a great first stop, but expect a wait. Head to Todd English’s Figs for one of the neighborhood’s newest outlets with contemporary twists on thin-crust pizza (the Isabelle includes country ham, aged provolone cheese, fresh asparagus, and sweet onion).

Beyond the North End, world-class eateries dot every corner of the city. At the Godfrey Hotel — one of the city’s newest hotels in Downtown Crossing— is Ruka. Situated in a bold, vibrant space, the menu is inspired by all things from the sea with a preparation that combines Japanese, Chinese, and Peruvian in a way that somehow just works. Take the Octopus Lomo Saltado — topped with onions, ginger soy, black rice, peppers, and shoestring fries. Don’t leave without an order of Suspiro Limeno — a Peruvian specialty similar to dulce de leche.

Boston

If you’re instead craving legit Mexican fare chased with good tequila, Lolita Cocina and Tequila Bar ought to satisfy your needs. It’s a dark, lively, intimate place with a funky menu and even funkier atmosphere (complimentary Pop Rocks and temporary tattoos are delivered with the check). Before even thinking about food — as difficult as that may be at Lolita’s — order one of their signature margaritas. They’re the best in the city.

For something completely different, head to Liquid Art House. This one-of-a-kind destination is at once a restaurant, lounge, showroom, and art gallery — all integrated under one roof. The owner, Ruta Laukien, deftly created an environment suitable for everyone that marries art with social dining. The large canvas behind the circular, central bar is the focal point of the experience and reflects the chefs, artists, designers, and nightly guests. It’s a lovely, intimate space perfect for a dinner date or nightcap with friends.

Pub Crawl Like It’s Your Last Night on Earth

Visitors needn’t look far for a properly poured cocktail in Beantown as there’s no shortage of gin joints (see also: The Hawthorne mentioned below). No visit to Boston is complete, however, without an actual pub crawl — and we mean pub, not bar. According to a study we made up for this post, the city boasts more Irish pubs than any city in the world outside of Dublin. Just resign yourself to the fact that you won’t hit them all in a week, let alone a single night.

The Black Rose

Start downtown at The Black Rose — a mainstay that’s among the city’s oldest pubs. It’s unabashedly old school with traditional Irish cuisine, legit Irish knickknacks throughout, and live music every night of the week. Afterward, head to Mr. Dooley’s, just a few blocks away. This longtime favorite among Irish Americans boasts an excellent whiskey selection, live music most nights, and (thankfully) not a single television. If it’s televised sports you’re after, The Banshee in Dorchester is the place. The Irish heritage here is as thick as the patrons’ accents, and there’s always a handful of rugby and football (we mean soccer) on at any given time. Or, if it’s a post-Guinness snack you’re seeking, hop an Uber to The Druid in Cambridge. It’s about as authentic Irish as it gets (the cod and house-made fries are a staple and served wrapped in newspaper just like the old country).

PLAN YOUR ESCAPE

Like many East Coast cities, one of the best ways to experience Boston is from the water. Nature lovers will appreciate a visit to Stellwagen Marine Sanctuary — the East Coast’s premier spot for whale-watching. Passengers aboard Boston Harbor Cruises’ whale-watching tours can spot dozens of whales, dolphins, and marine birds on a single cruise (plus, their tours are guaranteed). If a whale watch isn’t disco enough for you, check out BHC’s other tour boat — the insane Codzilla jet boat.

 Boston Harbor Cruises’ whale-watching tours

The city is within a two-hour drive of some of the best hiking on the east coast in New Hampshire’s White Mountains. However, if you’re short on time, head just four miles offshore to Spectacle Island, part of the Boston Harbor Islands. This 105-acre patch of green boasts a marina, a cafe, a sandy, swimmable beach, and five miles of hiking trails. All of which center around a 157-foot-tall hill (considered a “mountain” in these parts) with sweeping views of the Boston skyline. For more challenging trekking, the 7,000-acre Blue Hills Reservation guarantees more than enough hiking opportunities to keep even the most avid nature-lover occupied for a week.

WHERE TO STAY

Fall Asleep to the Cheers of Fenway Park

Hotel Commonwealth

For sports fans in general and Sox fans in particular, it’s hard to imagine more perfect lodging than Hotel Commonwealth. The hotel offers an approachable form of luxury through a tasteful decor, modern amenities, and two chic, world-class cocktail lounges (Eastern Standard and The Hawthorne). But, the big get for sports fans is the newly opened Baseball Suite and Fenway Park Suite. The latter is the hotel’s flagship room with 700 square feet (massive by Beantown standards) of living space and a large, walk-out balcony just 500 feet from Fenway Park.

Lock Up at The Liberty Hotel

Liberty Hotel boston

For sheer luxury, West End’s The Liberty Hotel may be the city’s most iconic accommodations. The one-time Charles Street Jail was converted into a boutique five-star hotel in 2007. It’s now best known for its stunning, four-story lobby atrium that doubles as a swanky, contemporary lounge that’s as popular with locals as with travelers. In addition to nearly 300 guestrooms, the hotel also offers five luxury bars and restaurants.

WHAT TO SKIP

At almost 90 square miles (four times the size of Manhattan), Boston is a sizable city. Unfortunately, there isn’t just one tourist area or neighborhood to avoid. In short, here are things to do in Boston you can absolutely skip:

  • Faneuil Hall: On paper, this historic market has a lot to offer: charming, 18th-century stone buildings, cobblestone walkways, a storied past when it served as the city’s hub of commerce for merchants and fishermen, and a connection to almost every major figure in Boston’s history. In reality, it’s home to “fake” Cheers, 100 mostly chain stores (including Abercrombie & Fitch and Crate & Barrel), and the city’s highest concentration of tourists. It’s beautiful from afar, but the few minutes you’ll spend here on your aforementioned walk of The Freedom Trail are all you need before moving along.
  • Chinatown: Most of America’s largest cities (San Francisco among them) boast distinct, beautiful Chinatown districts. Boston’s, by contrast, is small, run-down, and lacks an ounce of charm.
  • Roxbury: Quite simply, it’s the city’s most dangerous neighborhood. Stay far, far away.
  • (If you’re wearing Yankees attire, don’t go anywhere near Fenway Park. In fact, don’t leave Logan Airport without a cadre of armed security.)

PACK YOUR BAGS (WHEN TO GO)

Every year, New Englanders brave a long, dark, seemingly 13-month winter. So, when summer finally hits, locals make the best of every last hour of warmth and daylight.

Like everywhere in the Northeast, Boston experiences four distinct seasons. Summer is comfortable and warm (though rarely too hot). Spring and Fall are cool, breezy (a light jacket is always appropriate), and the best time to visit due to thinner crowds and lower prices on hotels and tours. Winters are cold — sometimes bitterly so — and snow is a real threat every other week.

South Boston St. Patrick’s Day Parade

But, with a long list of things to do in Boston every month of the year, ole Beantown is always worth a visit. Here are the city’s most noteworthy festivals and events:

  • March: With more Irish descendants per square mile than any city in the country, the St. Patrick’s Day shenanigans are almost enough to bring the city to its knees. The South Boston St. Patrick’s Day Parade is a great place to kick-off the day’s festivities.
  • April: Every April, the city hosts one of the largest, most celebrated marathons in the U.S. — the Boston Marathon.
  • June: The annual Boston Pride Week is New England’s largest event of its kind.
  • July: The Boston Pops Fireworks Spectacular is among the largest July 4th celebrations in the country. Every year, more than a million people line the banks of the Charles River to watch the massive fireworks display and experience an exclusive performance by the world-renowned Boston Pops.
  • September/October: With the country’s highest concentration of colleges/universities and (again) Irish folks, Boston loves to drink … a lot. So, it’s no surprise that its Oktoberfest celebrations (plural) are off the charts. Times and locations change every year, but Event 12’s Boston calendar is a good place to start your planning.