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Coastal & Cultured: Five Ways to Experience Boston History & Arts

With a past woven over almost four centuries, Boston offers a canvas of artistic escapades, historical adventure, and extraordinary entertainment where every cobblestone seems to tell a tale. For curious minds and cultural connoisseurs alike, consider us your personal concierge, curating your ideal itinerary with this guide to the city’s dozens of museums and galleries, world-class concerts, immersive tours, and seasonal events.

Galleries & Art Adventures

A natural first stop for an art adventurer is the Museum of Fine Arts Boston, one of the most comprehensive art museums in the world and home to true strokes of genius. You’ll stroll past masterpieces by Rembrandt, Van Gogh, Cezanne, and Gauguin — not to mention the finest collection of Monets outside of Paris. But that’s only the beginning. The museum’s expansive collection of paintings coexists with mummies from ancient Egypt, sculptures from China, ceramics from Vietnam, and artifacts from the Roman Empire.

The Isabella Stewart Gardner Museum — an architectural wonder modeled after a Venetian palazzo — is home to a spectacular collection of over 2,500 paintings, sculptures, rare books, and furniture across three floors. Its idyllic courtyard is a stunning landscape architecture experience, ideal for reading, sketching, or sipping something delicious from the café.

For more modern masterpieces, the Institute of Contemporary Art in the Seaport District is a must-visit. Actually, it’s a work of art itself. This gallery showcases a diverse and captivating collection of works, encompassing paintings, video, mixed media, photography, and sculpture along with amenities including a 330-seat theatre, a restaurant, and a bookstore.

Historical Landmarks & Legends

Bundle up and walk through the country’s history on The Freedom Trail, a 2.5-mile red-brick route through Boston’s historic neighborhoods and 16 renowned historic sites. Starting at the Boston Common  — America’s oldest public park  — you’re free to forge your own path and stop at attractions like the Massachusetts State House, Faneuil Hall, and Paul Revere House. You could easily spend an entire day walking the entire experience, or start at the Visitor Information Center to purchase a ticket for a shorter guided tour.

Explore the floating, interactive Boston Tea Party Ships & Museum for historical reenactments, multimedia exhibits, authentically restored tea ships, and a tearoom. Walk The Black Heritage Trail in Beacon Hill, showcasing the homes and community buildings of a thriving Black community formed during the nation’s earliest years. Visit the John F. Kennedy Presidential Library and Museum, an architectural marvel featuring curated galleries dedicated to showcasing JFK’s life and legacy, and a library housing literary works, including Hemingway’s masterpieces. Follow the Path of Presidents to uncover the artifacts, anecdotes, and historical locales of Greater Boston’s presidential past and learn how nearly every president influenced Boston’s history.

Boston Tea Party

Neighborhood Nooks & Architecture Tours

There’s no window into the past quite like a walk through Boston. Boston by Foot’s guided architectural tours will take you through some of the city’s most iconic neighborhoods, where you’ll soak in a few museums worth of history in a stroll. Explore The North End, the city’s oldest neighborhood, and Boston’s “Little Italy.” Discover the picture-perfect Victorian brownstone homes and architectural marvels of Back Bay. Wander by Federal-period mansions on charming cobblestone lanes in Beacon Hill — home to Acorn Street, one of Architectural Digest’s most beautiful streets in the world.

For festive exploration exploration, a Holiday Sights & Festive Nights Trolley Tour with Old Town Trolley Tours is a unique way to blend holiday tradition with tales of the past. Hosted by costumed character guides, you’ll learn about Charles Dickens’ nearby visit, stop at the Boston Commons to see the ice-skating rink and Christmas tree, and cruise down historic Charles Street for extraordinary décor sightseeing as you listen to the stories of the renowned writers and artists who called this street home.

Boston Children's Museum

Symphonies & Theatrics

A symphony of choices awaits the discerning music lover. For the classics, the Handel & Haydn Society a Grammy-winning orchestra and symphony — and the Boston Symphony Orchestra stand as cultural beacons. For more contemporary melodies, the Boston Symphony Orchestra’s second identity, The Boston Pops, offers light classical music in a laid-back setting. The Boston Pops experience is even more magical during the holiday season, with special concerts starring holiday favorites, plus sensory-friendly experiences and kids’ matinées.

Find a stage to suit your fancy and a little dramatic flair in the nearby Theater District, which overlaps with vibrant Chinatown. Discover a diverse array of Broadway productions and spectacular shows at dazzling historical theatres like Citizens Bank Opera House, Emerson Colonial Theatre, and Boch Center.

Iconic Boston Settings & Stories

Few things embody Boston’s identity quite like Fenway Park and Harvard University, and each offers unique insight into some of the city’s most interesting chapters. Sports history fans will love touring Fenway Park, home of the Boston Red Sox and the oldest stadium in Major League Baseball. Explore the ins and outs of this beloved ballpark’s hallowed halls, take in the views from the Green Monster (Fenway’s famous left field wall), and learn about all the legendary moments that have taken place since its opening in 1912.

Wander across the river to Cambridge and visit the famed Harvard University and Harvard Square neighborhood. Like a world of its own, it’s home to a host of historical structures, like Wadsworth House, Swedenborg Chapel, Memorial Hall, and all the gems of Harvard Yard. Harvard is also home to its own museums, including three Harvard Art Museums and four Harvard Museums of Science & Culture.

Fenway Park

Boston Beckons

Pair your impeccably-curated Boston getaway with the perfect offer. Our Curiosity & Reflection package includes day passes for two to the Boston Athenaeum — one of the oldest independent libraries in the United States — a Dagny-branded Moleskine journal, two Dagny-branded mugs, and a box of Boston Harbor tea with five tea bags.

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