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Your ultimate guide to Boston

Allison Tibaldi   

Your ultimate guide to Boston
Chiara Salvadori/Getty Images
  • Boston is one of America's most historic cities.
  • There are many hotel, restaurant, and activity options when planning a trip to Beantown.

With Puritan roots and a seminal role in the American Revolution, Boston is one of America's most historic cities. Walk the cobblestone streets and you can practically hear Paul Revere's midnight cry and see shadows of the colonists dumping tea into Boston Harbor. The past seeps from every crack and crevice, but nix the idea that a visit is going to be as stuffy as reading your AP US history textbook. Boston isn't defined by yesterday; rather, it retains traditions, blending them into the present in a relevant way. A fresh take on art, architecture, and food keeps New England's biggest city firmly planted in the 21st century.

Beantown mixes highbrow with lowbrow as seamlessly as a well-shaken cocktail. From blue-chip art at world-class museums to bold street murals, from munching on a hot dog at Fenway Park to eating Boston cream pie at the fancy hotel where it was invented, experiences run the gamut and needn't overextend your wallet.

An abundance of youthful energy makes it impossible to forget you're in a college town. For those who want to soak in extra brainpower, Harvard and MIT are just across the river in Cambridge, boosting collegiate moxie.

Get ready to explore Boston's patchwork of distinct neighborhoods, from the arty vibe in the South End to the patrician charms of Beacon Hill.

Getting to and around Boston

Getting to and around Boston
South Station opened on New Year's Eve in 1898.      Abdullah Al-Eisa/Getty Images

Boston benefits from excellent transportation links. Boston Logan International Airport is New England's largest and recently underwent a multibillion-dollar expansion and modernization project. Each of the four-passenger terminals features expanded dining and shopping options, plus free WiFi. Rocking chairs add a cozy touch, and a public art program adds eye candy so often missing from functional establishments. With direct flights from over 75 cities, there's a good chance you'll be on a nonstop. Logan is a convenient 2 miles from the city center. The city's subway system provides free access via the Silver Line. Taxis, Uber, and Lyft are also options.

If you're on the Eastern Seaboard, Amtrak has robust service from New York, Philadelphia, and Washington, DC. Both Northeast Regional trains and high-speed Acela service stop at South Station and Back Bay Station. If you're coming from New Hampshire or Maine, the Amtrak Downeaster arrives and departs from North Station.

South Station also serves as the city's bus depot. Greyhound and discount Megabus are popular coach options. South Station has a variety of fast-food eateries, but foodies can walk a few blocks to Chinatown and purchase plump steamed dumplings to go. Eat them once you're on board and watch your envious fellow passengers salivate.

To get around Boston, ride the color-coded subway, officially named the Massachusetts Bay Transportation Authority, known as the "T" by locals. You'll need to purchase a CharlieCard or CharlieTicket, available at station kiosks and some convenience stores. The T shuts down for several hours each night, though buses continue to provide service.

The Bluebikes public bike-share program offers thousands of bikes, with adjustable seats and sturdy frames, at hundreds of kiosks around town. Purchase a single trip or day pass and pedal away.

Where to stay in Boston

Where to stay in Boston
Beacon Hill's Liberty Hotel once housed Boston's criminals between 1851 and 1990.      Katie DeMonte for Insider

Mirroring the city itself, hotels include dignified old-world, vibrant takes on contemporary style, and several that have been inventively repurposed from existing structures. Book a room near Back Bay, Beacon Hill, the South End, or Boston Harbor, and you'll be within walking distance from many attractions.

In a landmark South End building, the inexpensive Revolution Hotel is an adaptive reuse of one of the first YWCAs in the US. Guests are surrounded by art that pays homage to Boston's history, including a foyer mural that incorporates Samuel Adams into the scheme.

Another with the theme of repurposing is Beacon Hill's Liberty Hotel, which was once a jail. The structure has been imaginatively transformed, while honoring the building's architectural integrity. Winding catwalks, wrought iron on the windows, and preserved jail cells in the restaurant demonstrate a preservationist ethos, while adding cheeky design elements.

Admirers of yesteryear will enjoy the gracious vibe at Beacon Hill's Omni Parker House, with roots dating back to the mid-19th century. Crystal chandeliers and ornate hand-carved woodwork add to the distinguished atmosphere. It's a must for serious epicureans, as the recipes for Parker House rolls and Boston cream pie were invented here.

For modern luxury with a side order of nautical charm, Boston Harbor Hotel is on the waterfront. With expansive water views, an indoor pool, spa, and fitness center, it feels like a resort in the city — but you're walking distance from many attractions.

For a lesson in swank, the pricey Mandarin Oriental in Back Bay benefits from decor with a sophisticated edge that looks stolen from a James Bond film. If you're in the market for some pampering, it's home to one of the city's best spas.

What to eat in Boston

What to eat in Boston
Mike's Pastry was founded in 1946 in Boston's historic North End on Hanover Street.      Katie DeMonte for Insider

The simple, straightforward style of cooking that the pilgrims brought with them has long been replaced by an eclectic dining scene filled with global influences and flavors that represent the city's diverse population.

That doesn't mean you shouldn't sample tried-and-true Yankee classics. Illustrious locals with surnames like Kennedy still flock to Union Oyster House on the Freedom Trail near Faneuil Hall. The menu, largely unchanged for two centuries, features fresh Atlantic seafood such as briny oysters, New England clam chowder, and broiled scrod served with vintage sides like baked beans and cornbread. Colonial-style desserts include home-baked gingerbread and warm Indian pudding topped with soft peaks of whipped cream.

Italians have been immigrating to Boston for generations, and the North End is the city's Little Italy. At Bricco, the smell of olive oil, barrel-aged vinegar, and prosciutto transports you to the old country without a passport. Order light-as-a-feather pasta, creamy risotto, or the tomato-based fish soup brodetto, which is teeming with lobster. The menu also features Wellfleet clams, mussels, calamari, shrimp, and monkfish.

For dessert, the cannoli rivalry between Mike's Pastry and Modern Pastry, both on Hanover Street, is as real as New Haven's pizza rivalry. Try them both and decide for yourself.

Lucy Ethiopian is an unassuming place on Massachusetts Avenue. If you're not familiar with this flavorful cuisine, this is the place to explore the seasoned meat, legume, and vegetable stews that you scoop up with injera, a spongy flatbread made with fermented teff flour. There are numerous vegetarian and vegan dishes.

At Anoush'ella in the South End, the owners serve mouthwatering Eastern Mediterranean food that harkens back to the Armenian and Lebanese street foods of their childhoods. Flaky hand-rolled flatbreads are wrapped around fresh ingredients such as hummus, baba ghanoush, spiced minced lamb, and lentils. Soups, salads, and grains are healthy, inexpensive, and delicious. They have an additional outpost at the Time Out Market near Fenway.

Roxbury is a residential neighborhood with a strong sense of community pride. Dudley Cafe embodies this identity. It's a casual eatery that partners with nearby high schools, training students and creating job opportunities for them. Mingle with regulars, dine on wholesome food, and listen to live music performed by local talent.

When it's time for an alcoholic beverage, Boston has plenty of tricks up its sleeve. Shore Leave in the South End serves retro-style tropical cocktails, like a Blue Hawaii, in a whimsical setting. Burgers, wings, tater tots, and hot dogs are the perfect accompaniments.

Craft-beer lovers have a lot of choices, but hopheads shouldn't miss the taps at Trillium Brewing, where the double-dry hopped varieties have a loyal fan base. They have several locations, including Fort Point in the Seaport District and a beer garden at the Rose Kennedy Greenway.

Activities in Boston

Activities in Boston
Founded in 1634, Boston Common is the oldest city park in the United States.      Katie DeMonte for Insider
Art

Boston is a feast for anyone with an eye for visual art, whether you gravitate toward ancient or innovative styles. From Egyptian mummies to Colonial portraiture to impressionist paintings, the Museum of Fine Arts is home to one of the most comprehensive collections.

The Isabella Stewart Gardner Museum is housed in a building modeled after a 15th-century Venetian palazzo with works by Botticelli, Michelangelo, and Rembrandt. Majestic tapestries, grand furniture, and a spectacular courtyard are some of the many treasures. If your name happens to be Isabella, you'll get in free of charge.

Visitors with a thirst for experimental visuals will enjoy the Institute of Contemporary Art, housed in a stunning building directly on the waterfront in the Seaport District. The museum embraces diverse art forms, including music, film, and video art.

For dynamic art in the fresh air, Underground at Ink Block is an 8-acre underpass that has been transformed into a cultural hot spot filled with striking murals. Between the South End and South Boston, it's a vibrant place to experience the intersection between community and art.

The Rose Kennedy Greenway is a 1 1/2-mile-long sliver of urban park with temporary public art installations set against a wonderland of fountains and flora in the heart of the city. Kids (and kids at heart) shouldn't miss a spin on the one-of-a-kind carousel, which features animals native to the region, such as lobsters and harbor seals.

Historic trails

Boston's manageable size makes it a great walking city. Follow in the footsteps of our Founding Fathers on the Freedom Trail. Strolling this 2 1/2-mile red-brick path sheds light on this city's pivotal position during the American Revolution. It traverses 16 historically significant sites, including the Bunker Hill Monument, where the first major battle of the American Revolution took place.

The Black Heritage Trail is a 1.6-mile path that underlines the history of Boston's thriving 19th-century African American population and the leadership role the community played in the abolitionist movement. Trail highlights include several stations on the Underground Railroad and the African Meeting House.

Urban greenery

Bostonians are spoiled with a wealth of outdoor spaces. The Emerald Necklace is a series of parks designed by Frederick Law Olmsted, including the Public Garden, America's oldest public botanical garden. Acres of grassy lawns, exotic plants, and whimsical swan boats cruising the pond provide a leafy respite.

Boston Common is across the street. Though it's technically a separate entity, it feels very much part of the Public Garden. Locals skate on the smooth ice of Frog Pond during colder months.

To get a feel for Boston's geographic position, explore one of the 34 islands sprinkled throughout Boston Harbor. They provide serenity, seaside landscapes, and a sense of remoteness only a few miles from the city center. About a dozen of the Boston Harbor Islands are accessible to the public via ferry at Long Wharf North in the summer months. Spectacle Island has lush seagrass, colorful wildflowers, and sandy beaches, making an invigorating swim possible.

The Charles River cuts through the heart of Boston. Walk or cycle along the esplanade, watch students row crew, or enjoy the water with a stand-up paddleboard, kayak, or canoe.

Advisories to know when traveling to Boston

Advisories to know when traveling to Boston
When visiting Boston, make sure to pay attention to the city's local advisories.      Katie DeMonte for Insider

Boston fully reopened in May, with all COVID-19 restrictions and capacity limits lifted. Fully vaccinated people do not have to wear face coverings indoors or outdoors, with the exception of mandatory face coverings when riding public and private transportation, including ride-hailing trips, taxis, buses, subways, and ferries.

Nonvaccinated people are advised to continue using masks and social distancing.

Boston and the state of Massachusetts have a high vaccination rate, though the situation is fluid. We recommend following the advice of the Centers for Disease Control and Prevention, the World Health Organization, and other reputable agencies.

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