Boston in Six Days: Fun, Food, and Fantastic Sights

Ready for six unforgettable days in Boston? Here’s your ultimate itinerary!

Boston Harbor at Sunset

You’ve got six whole days in Boston—plenty of time to soak up Revolutionary history, indulge in legendary seafood, and wander through quirky neighborhoods. Whether you’re coming for cobblestone charm or world-class museums, Boston packs plenty into every block. Over the next six days, we’ll guide you through classic attractions, hidden gems, and some of our favorite spots to eat, drink, and unwind after all that exploring. 

Our favorite things to do in Boston include: 

  • Freedom Trail Foundation® Walk into History Tour 
  • Museum of Fine Arts 
  • Boston Harbor Walk & Seafood Tour by Top Dog Tours 
  • Boston Children’s Museum 
  • The Harvard Tour 
  • Boston Movie Mile Walking Tour by On Location Tours 
  • Isabella Stewart Gardner Museum 
  • North End ‘Little Italy’ Food Tour by Top Dog Tours 
  • USS Constitution Museum 
  • View Boston 
  • Salem Witch Museum 
  • LEGO Discovery Center 

Day 1: Boston Classics and the Freedom Trail

Freedom Trail Tour Guides

Grab your most comfortable shoes; today’s all about cobblestones, red bricks, and fascinating stories. 

Morning: Start at Boston Common—America’s oldest public park—and join the Freedom Trail Foundation® Walk into History Tour. This guided walk brings to life tales of rebellion and daring escapes, weaving you past 16 historic sites. Stroll through the leafy lanes and feel history around every corner. 

Lunch: After your walk, you’ll be a stone’s throw from Quincy Market. Stop at Boston Chowda Co. inside Faneuil Hall Marketplace for a creamy, rich cup of New England clam chowder. The centuries-old market buzzes with local vendors and hungry visitors, so sit on the steps outside to people-watch as you dig in. 

Afternoon: After lunch, take a short walk (under 10 minutes) to the Old State House Museum & Old South Meeting House. Here, you’ll find galleries filled with artifacts and stories that shaped the country. The mix of interactive exhibits and original period rooms sets the stage for even more historical insight. 

Free Time Tip: Wander the leafy Beacon Hill neighborhood nearby. Its gas-lit lanterns and brick sidewalks ooze old Boston charm—the perfect spot for some dreamy photos. 

Dinner: Head to Union Oyster House—America’s oldest continuously operating restaurant—for fresh oysters and Boston specialties. The lively tavern vibe and historic memorabilia create a memorable first-night atmosphere. 

Day 2: Museums and Artistic Inspiration 

Today’s about culture, masterpieces, and local creativity—with a little science thrown in. 

Morning: Take the T (Green Line E) to the Museum of Fine Arts. This stunning space offers everything from ancient Egyptian sarcophagi to Impressionist paintings. We always love wandering the rotating exhibits and grabbing coffee in their sunny courtyard café for a well-earned break. 

Lunch: Walk about 10 minutes across beautiful Fenway to Time Out Market Boston. These communal food halls are a trend for a reason: try a juicy burger from Craigie Burger or Vietnamese spring rolls from Ms. Cluck’s Deluxe. Local mural art adds a fun, bustling vibe. 

Afternoon: Jump back on the T (Green Line E, then transfer to the C) to reach the whimsical Isabella Stewart Gardner Museum. This Venetian-style palace bursts with fascinating art, lush courtyard gardens, and a mysterious unsolved art heist that adds intrigue to its aura. 

Dinner: Stroll through the nearby Fenway neighborhood (especially lively on game days!) to El Pelón Taquería for freshly made fish tacos and housemade aguas frescas in a casual, colorful spot beloved by locals. 

Day 3: Waterfront Fun and Boston Science

Boston Harbor

Get ready for a day of discovery, with waterfront views, interactive exhibits, and plenty to keep curious minds busy. 

Morning: Head to the Seaport (Silver Line SL1/SL2) for the Boston Harbor Walk & Seafood Tour by Top Dog Tours. Savor delicious local seafood while discovering cool stories behind the city’s blue-collar wharves and modern waterfront buzz. 

Lunch: Lucky you—your tour takes care of lunch today! Sample classics like lobster rolls or fried clams at hidden gems you might never find on your own. 

Afternoon: A breezy 10-minute walk along the waterfront brings you to the Boston Children’s Museum. This hands-on wonderland is perfect for kids, but just as fun for grownups who want to play. 

For something more science-y, stroll 15 minutes upriver to the Museum of Science. Touch the lightning in the Theater of Electricity or take in perfectly produced planetarium shows. If your group prefers, swap this for the USS Constitution Museum to climb aboard “Old Ironsides” and feel the power of Boston’s maritime history. 

Dinner: Cross the Charles River via the Museum of Science pedestrian bridge to The Friendly Toast in Cambridge—a funky diner with an all-day breakfast menu, eccentric decor, and big, playful plates (we’re partial to the chicken and waffles). 

Day 4: Cambridge, Harvard, and MIT 

It’s time to cross the river and rub elbows with students and scholars. 

Morning: Take the Red Line to Harvard Square. Join The Harvard Tour—an enthusiastic student-led stroll through Harvard Yard, crammed with wild stories, fun traditions, and gorgeous old architecture. 

Lunch: Go for a slice from Pinocchio’s Pizza, a local legend with square Sicilian-style pies and walls lined with sports photos. Grab one of the coveted stools or take your pizza to go and lounge in the Harvard Yard. 

Afternoon: Walk or hop on the T one stop to Central Square for the MIT Tour. Marvel at the modern campus buildings (Gehry’s Stata Center will have your camera out in a flash), and learn quirky student “hacks” from your guide. 

If you’re after a culture hit, pay a visit to the Harvard Museum of Natural History or the Peabody Museum of Archaeology & Ethnology—both are right next door on campus. 

Dinner: Wind down your day at Harvest, a modern New England institution just off Harvard Square, known for its creative seasonal fare and hidden garden terrace. Try the roast chicken or the chef’s daily pasta special. 

Day 5: Day Trip—Salem or Concord?

Salem Witch Museum

It’s time to explore beyond the city and delve into New England’s charming towns. Choose your own adventure! 

Option 1: Salem 

Morning: Take the commuter rail from North Station (about 30 minutes) to Salem. Explore the Salem Witch Museum, then head to the House of the Seven Gables and Real Pirates Salem. 

Lunch: Finz Seafood & Grill has great harbor views and excellent lobster rolls. 

Option 2: Concord 

Morning: Take the Fitchburg Line to Concord (40 minutes). Visit the Concord Museum and Louisa May Alcott’s Orchard House. Both are walkable from Concord Center. 

Lunch: Woods Hill Table—a cozy, farm-to-table spot known for its grass-fed burgers. 

Afternoon: No matter which town you choose, both deliver a dose of history, small-town charm, and a break from Boston’s urban pace. If you're keen to linger... 

  • In Salem, stroll Chestnut Street’s Federal mansions or peek into the quirky shops along Essex Street. 
  • In Concord, stop by Sleepy Hollow Cemetery (resting place of literary greats), or take a leafy walk by Walden Pond. 

Evening: If you’re feeling hungry again when you’re back in Boston, wrap up your day in the North End with a classic cannoli and an espresso at Modern Pastry—best enjoyed as you reminisce about your excellent day out. 

Day 6: North End & Neighborhood Adventures 

Morning: Take the T to Haymarket and meet your guide for the North End ‘Little Italy’ Food Tour by Top Dog Tours. Sample cannoli, arancini, and legendary pizza in this music-filled, tight-knit neighborhood packed with Old World charm. 

Lunch: Your tour takes you from bakery to salumeria, but if another meal is needed, grab a classic Italian sub from Monica’s Mercato. 

Afternoon: Burn off lunch with a walk to the Paul Revere House or hop over to the waterfront for the Boston Movie Mile Walking Tour by On Location Tours—you’ll recognize plenty of filming spots from TV and film! 

If you’re traveling with little ones or LEGO enthusiasts, the LEGO Discovery Center at Assembly Row (Orange Line, Assembly stop) provides hours of fun. Kids can build, play, and ride in a creative world of colorful bricks—and adults will find themselves sneaking a build or two as well. 

Evening: Before your last night in Boston wraps up, catch the sunset at View Boston, the city’s sky-high observation deck at the Prudential Center. Glide up just as the sun dips behind the Charles River, with the entire city lighting up beneath you. This panoramic view will be a standout memory from your trip. 

Dinner: Head for Eataly Boston right inside the Prudential Center. The food hall’s casual dining spots serve up fresh pastas, wood-oven pizzas, and creamy gelato. 

Free Tip: If you’re keen for more post-dinner strolling, Copley Square, Trinity Church, and the Boston Public Library are especially lovely at night, with golden lighting and a surprisingly peaceful vibe for city wanderers. 

 

Your six days in Boston will leave you with more than just phone-fulls of photos. Whether you’ve debated revolutionaries along the Freedom Trail, tasted your way across the North End, or strolled the storied halls of Harvard, you’ve experienced Boston’s unique mix of New England charm, culinary delights, and top-notch attractions.  

Enjoyed this? Check out Everything You Need to Know About Go City’s Boston Passes or Things to Do as a Family in Boston  

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We make it easy to explore the best a city has to offer. We’re talking top attractions, hidden gems and local tours, all for one low price. Plus, you'll enjoy guaranteed savings, compared to buying individual attraction tickets.   

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Public park in Boston with a walking trail
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Best walks in Boston

On your marks, get set... walk! That’s the way to do Boston, anyway. Unassuming, academic and full of history, this city is the ideal place to stretch your legs as it’s also very accessible, very flat, and very pretty. There’s a good mix of city lights and green spaces, and the Charles River winds serenely on its way to Massachusetts Bay offering lovely walks along the esplanade. Beware the weather – the icy wind off the Atlantic can make things pretty wet and chilly in winter – but don’t let it put you off! Fuel up on some Boston baked beans, grab your raincoat and try out one of these awesome Boston walks: The Freedom Trail Financial District to the Theater District The Movie Mile Harvard to MIT The Battle Green Tour The Emerald Necklace Trail The Freedom Trail Many key events of the American Revolutionary War took place in Boston, and a lot of these historical sites are now accessible to visitors. To make it easy, 16 of them are connected by the 2.5-mile Freedom Trail which runs from Boston Common to Bunker Hill. It’s marked by a red path on the ground so you can’t really get lost – but if you’re finding all the history a little disorientating then use your pass to take a Freedom Trail Foundation guided tour. It covers 11 of the 16 sites on the trail, including Massachusetts State House, the USS Constitution and the site of the Boston Massacre. Your guide – complete in 18th century costume – will share all the stories of revenge and revolution so you won’t get your dates and declarations in a tangle. The Financial District to the Theater District This easy walk gives you a great overview of the modern and historic side of Boston in just a couple of hours. Start at the World Trade Center bus stop and enjoy the view of the wharf and Congress Bridge before exploring the financial district. Here, as well as being able to witness Boston’s buzzing economy in motion, you’ll find the Boston Children’s Museum, the Boston Tea Party Museum, King’s Chapel and Burial Ground and the Irish Famine Memorial. Soak up the history, then go for some retail therapy at Downtown Crossing before heading towards the Theater District via Washington Street and Tremont Street. This route will take you past Chinatown, which makes a colorful diversion if you’re feeling peckish, and you’ll come out by the Shubert and Wang Theaters. From here, it’s an easy saunter to Boston Common, where you can either have a look around Emerson College Campus or just flop down on the grass and give your legs a rest. The Movie Mile Many of Boston’s iconic landmarks are familiar to us because we’ve seen them so often on film and television – so why not get to know them in person? Take the Boston Movie Mile Walking Tour with Go City and discover over 30 locations you may have seen in films like Ted, Good Will Hunting and The Departed, or TV shows like Ally McBeal and Cheers. You’ll take in quiet, unassuming neighborhoods, historic homes, the original Cheers pub and the bench where Robin Williams and Matt Damon shot one of their most famous scenes. Make sure your big and small screen trivia knowledge is up to date, as your guide may just quiz you along the way! Harvard to MIT This is a great walk that combines two of the city’s most famous institutions with a generous taste of student life in the city. North of the river in Cambridge, these two academic heavyweights are only a mile or so apart, but a slightly detoured route will also take you past Harvard Stadium (home of the New England Patriots until the 70s) and Harvard Business School. Explore Harvard Square on your own or join a guided tour, then head west over the Anderson Memorial Bridge towards the stadium. If you’re lucky, there might be a game going on, if not, it’s still worth a wander around. From there, turn down Harvard Way past the Baker Library to the Business School, and then circle back to the river and use the Western Avenue Bridge to cross back over. Turn left and walk along the river to Magazine Beach, then head east towards MIT. If you need more intellectual inspiration, you can take another guided tour, or check out the List Visual Arts Center. The “Let it Begin Here” Battle Green Tour Take a deep dive into American Revolutionary History with a guided tour of Lexington Battle Green, included with your Go City Boston Pass. This small area is of huge historical significance, being the place where the first shots of the war were fired. See the Old Belfry that sounded the alarm, the Buckman Tavern where nervous militiamen gathered the night before the battle, the Revolutionary War Monument, the Old Burying Ground and the Henry H. Kitson Minuteman Statue. Hear stories of how the battle unfolded, George Washington’s thoughts on the whole affair, and the meaning behind the famous “Stand your ground” inscription. You’ll also see some houses and other buildings dating from the same era, so you can really feel that you’ve traveled back in time. The Emerald Necklace walk A favorite among locals and visitors alike, this walk gets its name from the way it links a chain of sparkling parks and green spaces through the city. It’s a great one if you want to get away from the concrete jungle and give your legs a proper stretch – it’s around nine miles and does include some elevation, so allow up to four hours – more if you want to stop for a picnic somewhere! Start in Franklin Park – Boston’s largest, where you’ll also find the Franklin Zoo. From here, the walk takes you through the Arnold Arboretum at Harvard University, Jamaica Pond, Olmsted Park and along the Riverway to Muddy River. This route also takes you past the Isabella Stewart Gardner Museum and the Museum of Fine Arts. Continue along the long, green space that is the Commonwealth Avenue Mall all the way to the Public Garden, then either cross the suspension bridge or take the left path past the Robin Williams Memorial Bench. Finish by exploring Boston Common and be sure to take a selfie in front of Brewer Fountain! Step it up with Go City You can walk pretty much anywhere in Boston! Make sure you don’t miss anything with a Go City Explorer or All-Inclusive Pass and save on dozens of attractions around the city.
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