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A Traveling Insider’s Guide To Boston

Create your perfect itinerary for a Boston vacation by using this expert’s guide to the City Upon a Hill. By Paul Oswell | July 30, 2021

From the Boston Tea Party to the Battle of Bunker Hill to the site of Paul Revere’s ride, Boston is an American history buff’s dream. The city has been the site of momentous military and political battles, home to multiple presidents and today is one of the world’s greatest clusters of elite universities. It’s no wonder locals know it as “The Hub.”

But Boston is so much more than its history. In our guide, we’ll offer our rundown of the can’t-miss, memorable things to do in Boston. Here are some ideas for your trip:

  • Historic highlights: Walk the red bricks of the Freedom Trail to learn how the nation evolved and see the 19th-century row houses and gas lamps that make up Beacon Hill.

  • Cultural classics: Attend a concert by the Boston Pops, wander through the galleries filled with classic American and European paintings at the Museum of Fine Arts or take in a Red Sox game at the “lyric little bandbox” known as Fenway Park.

  • Outdoor opportunities: Picnic in the Emerald Necklace’s 1,100 acres of parkland, kayak along the Charles River or ride a Swan Boat in the Public Garden, America’s oldest botanical garden.

Why should you visit Boston?

Boston is a city that never sits still. Each Boston neighborhood has its own character and charm. In its heart is the Boston Common and Public Garden, an iconic public square often buzzing with locals and tourists, set against the majestic State House and its brilliant golden dome.

You can take in so much along the city’s cobblestone streets, seeing the sites that mark events from the Revolutionary War. Federal buildings line quaint Beacon Hill, while classic brownstones give the Downtown area a distinguished air. The city celebrates high culture through the world-class museums and theaters.

The city is built around its harbor, and the Boston Harborwalk has 43 miles of piers, parks, wharfs and urban beaches, as well as numerous ways to take in or even get out onto the water. You can check out collegiate rowing crews as they glide down the Esplanade.

Green and serene

The parks in the suburbs link up to the Boston Common and Public Garden via the Emerald Necklace, a chain of green spaces that has existed since the late 19th century. Take your family for a picnic on Constitution Beach after a hike along a natural trail on Boston Harbor Islands.

Its location also means a steady supply of fresh, mouthwatering seafood, from lobster rolls to oysters to a bowl of clam chowder. You can top it off with the official state dessert of Massachusetts: a Boston Cream Pie.

Foodies rejoice

We also love to grab grub in Chinatown, Brookline and the North End and East Boston (or Eastie, as it’s called). The Seaport district has been exploding with new restaurants in recent years.

When is the best time for your trip to Boston?

When you factor in the combination of things to do and the weather, you’ll land on June through October as the best times to visit. Spring in Boston typically brings highs in the 60-degree Fahrenheit (around 16 degrees Celsius) range, increasing throughout June to summer averages of low-to-mid 80 degrees Fahrenheit (around 27 degrees Celsius).

Hilton hint:

"If you're traveling in warm weather, head to Beacon Hill's Charles Street to pick up picnic supplies, then walk over to the Esplanade for a relaxing alfresco lunch while you watch the activity along the Charles River." - Hannah Cheney, Hilton Team Member, Content Marketing

Winter is frigid, with snowstorms possible from November through April. This can bring its own beauty to the place, but you’ll need plenty of warm clothes.

Boston is very much a college town, so room rates tend to spike in May around commencement and again in September during move-in weekends.

Getting to and around Boston

Logan International Airport is a busy hub that’s 2 miles from downtown. It can be easily reached by taxi, bus or the train (known as the T) and even water taxi. Taxis and ride-sharing apps all operate in abundance.

You’ll avoid the notoriously busy traffic and parking if you use public transportation and taxis. The city’s bike share program, Bluebikes, operates around the city. Hybrid bikes are available for rental at places such as Papa Wheelies or Landry’s Bicycles.

Things to do in Boston

Start your discovery walking the 2.5-mile Freedom Trail, a go-at-your-own-pace monument to Boston’s past. Make a stop or join a free weekday tour at the Massachusetts State House, an architectural wonder built in 1798. Next, head to the Black Heritage Trail, which explores sites including the oldest surviving Black church in the U.S.

Boston’s world-class museum offerings start with the Museum of Fine Arts, where visitors can explore half-a-million pieces of art and artifacts. In the Roxbury neighborhood, the National Center of Afro-American Artists houses over 3,000 objects.

If that whets your art appetite, then head to the Venetian-style palazzo of the Isabella Stewart Gardner Museum. Known as much for the famous art heist in 1990 as its current displays, it exudes Renaissance charm and houses more than 7,500 eclectic artworks from around the world.

The city’s Museum of Science has interactive exhibits to engage the gray matter and its awe-inspiring domed IMAX theater soars five-stories high. Harvard’s Art and Peabody Museums are open to the public, the latter having a whole wing dedicated to archeology.

Ignite creativity

For the kids, Boston Children’s Museum is a well-loved funhouse with a wealth of interactive exhibits. The excellent New England Aquarium and Harvard Museum of Natural History will appeal to nature lovers.

Try a Duck Tour for a land- and water-based overview of the city with your group. For your thrill-seekers, there are the always-spooky nighttime ghost tours, featuring a more haunting side of the city’s history.

Foodies will do well to start their exploration at either Boston Public Market or SoWa Open Market. If you choose Italian in the North End, you can end your night with a cannoli from the famous Mike’s Pastry or the delicious Modern Pastry.

No trip would be complete without seeing the famous Faneuil Hall Marketplace, which houses everything from name-brand stores to artisanal boutiques. It has an eclectic display of food stalls where you can find everything from ice cream to lobster rolls. Take in a street performance just outside the doors while you peruse.

Strike a chord

Boston’s music scene is also one of its strengths. Venues such as The Middle East, Paradise Rock Club, Brighton Music Hall and House of Blues have hosted all the greats — often before they became famous. The Orpheum Theater is the city’s oldest venue, and you’ll find touring bands and comedy here regularly.

We love the Italian Renaissance-style architecture of the city’s Symphony Hall. Hearing the Boston Symphony Orchestra and the Boston Pops perform amid its perfect acoustics is transcendent.

Boch Center-Wang Theater is equally decadent, and here you’ll also find touring Broadway shows. The city’s theatrical hub is Boston Center for the Arts and the Boston Opera House sits resplendent after its 2004 renovation.

Boston culture and customs

Boston is a large, diverse city. Bostonians are known for their intense sports team loyalties. Even if you’re not a fanatic, consider attending a baseball game at Fenway Park, seeing the Celtics at the TD Garden or just belly up to the nearest bar if the New England Patriots (who play in suburban Foxboro) have a big game.

The city has a large service industry. You should plan to tip at least 20% in restaurants, 10-20% for cabs and a dollar per drink minimum in bars, or more if you’re drinking fancy cocktails.

For visitors with an interest in American history, it’s hard to think of a more important city than Boston, and even beyond the treasures of the Freedom Trail, the past permeates Boston’s streets. Added to this fascinating backdrop is a city with a connection to the water through its harbor and islands, and outdoor exploration can continue on through Boston’s gardens and parks. A dynamic relationship to food, sports, performing arts and music all contribute to a rich urban texture, and wherever your interests lay, you're likely to leave Boston with a wealth of memories.

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Paul Oswell is an award-winning travel writer and has reported from all seven continents for dozens of internationally known publications. He is based in New Orleans and is the author of “The Bucket List North America: 1,000 Adventures Big and Small” and the editor of an online travel magazine.

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