Boston with Kids: The Ultimate 5-Day Family Itinerary for History, Food & Fun

Where to eat, what to see, and how to make the most of vacationing with kids in Boston. Discover every detail from our unforgettable family trip to this beautiful, historic, and incredibly walkable city.

We recently returned from the most incredible family vacation to Boston, accompanied by our four fantastic kids, ranging in age from 9 to 14. We simply couldn’t wait to share every memorable moment and meticulously planned detail with you!

Boston holds an exceptionally special place in our hearts. Years ago, my husband, Brandon, and I called Cambridge home while he pursued his business degree and I worked at the university. In fact, our eldest son, Baker, was born in Boston just before we relocated. This recent trip served as a perfect blend of heartwarming nostalgia and thrilling family adventure, allowing us to revisit cherished memories while creating exciting new ones through our children’s eyes.

To maximize our experience and ensure a relaxed pace, I thoughtfully organized our itinerary by dividing the city into distinct sections for each day. This strategy worked flawlessly, allowing us to explore efficiently without ever feeling rushed. Boston is renowned for its walkability, rich historical tapestry, exceptional culinary scene, and an abundance of engaging activities suitable for every age group. Here’s a detailed look at how we spent five perfect days—comprising four full days and two half days—in one of our absolute favorite cities.

Day 1: Evening Arrival & A Grand Culinary Welcome

• Our journey began with a late evening arrival, filled with anticipation for the adventures ahead.
• We checked into the exquisite Four Seasons Place, strategically located directly across from the picturesque Boston Public Garden and Boston Common. We enthusiastically recommend this hotel for its unparalleled location, luxurious comfort, and genuinely family-friendly service, making it an ideal base for exploring the city.
• For our late-night dinner, we ventured to Contessa on Newbury Street. This restaurant offered the most breathtaking panoramic views of the city skyline, brilliantly illuminated against the night sky, complemented by a deliciously creative Italian menu. Every dish we savored was a masterpiece, making it arguably our favorite meal of the entire trip – a truly perfect and memorable start to our Boston adventure!

Day 2: Immersed in History & The Vibrant North End

• We kicked off our day with a delightful breakfast at Thinking Cup, fueling up for a day of exploration.
• A leisurely stroll through the iconic Boston Common provided a refreshing start before diving into history.
• Our historical journey began on The Freedom Trail, guided by an affordable $3 map from the Visitor Center. This self-paced approach allowed us to fully absorb the significance of each stop, with the kids enthusiastically taking turns reading about the historical context and importance of sites like the Old State House and Paul Revere’s House.
• A quick and delightful stop at the historic Omni Parker House hotel was essential for tasting their legendary Original Boston Cream Pie and the famous Parker House Rolls, served in the elegant Parker’s Bar. This place truly breathes history!
• Lunch was a step back in time at Union Oyster House, proudly America’s oldest continuously operating restaurant. Indulging in their creamy clam chowder and another slice of Boston Cream Pie was a must-do tradition.
• Afternoon treats included refreshing Apple Cider Slushies and warm, mini cider donuts from Red Apple Farm, conveniently located inside the bustling Boston Public Market.
• We then immersed ourselves in the lively atmosphere of Quincy Market and Faneuil Hall, enjoying the diverse food stalls, unique shops, and street performances.
• Our exploration continued with a picturesque walk through the charming cobblestone streets of Beacon Hill, where we enjoyed window shopping and discovered the delightful Beacon Hill Books & Cafe, a cozy spot perfect for a quick break.
• A serene walk through the Boston Public Garden followed, highlighted by seeing the beloved Make Way for Ducklings statues and watching the iconic Swan Boats glide across the lagoon.
• A much-needed rest at the hotel allowed us to recharge before an exciting evening exploring the historic North End, Boston’s vibrant Little Italy.
• Our evening in the North End began with some playtime at Langone Park, letting the kids burn off some energy. Dinner at Antico Forno was a highlight, offering fantastic pizza and pasta dishes, and conveniently accepting reservations. We concluded our culinary tour with a traditional stop at Mike’s Pastry, where their cannoli remain our absolute favorite!

Day 3: Cambridge – A Journey Through Academia & Cherished Memories

• We started our day with delectable pastries from Flour Bakery near Boston Common before hopping on the “T” (Boston’s subway system) to Harvard Square.
• Exploring the prestigious Harvard University campus and its vibrant surrounding area, Harvard Square, was a fascinating experience. We browsed at The COOP and the iconic Harvard Book Store, where we were delighted to find my cookbook, Brilliant Bites, in stock!
• Lunch was a classic burger experience at the quirky and beloved Mr. Bartley’s Burger Cottage, a Harvard institution that never disappoints.
• We indulged in refreshing ice cream at JP Lick’s – it was just as delicious as we remembered from our time living here!
• The boys particularly enjoyed crossing the Charles River to visit Harvard’s historic football stadium and Harvard’s Basketball Pavilion, soaking in the athletic history.
• A walk around Harvard Business School was deeply nostalgic. We had so much fun showing the kids our old stomping grounds, recreating baby photos of our son, Baker, in front of Baker Library (which he was named after!), and even visiting Brandon’s old classroom, sharing stories from our past.
• We also took a moment to walk by our charming old home on Hingham Street in Cambridge, appreciating its 1854 charm and reminiscing about the speakeasy-turned-laundry-room in its basement.
• An afternoon snack at Alive & Kicking Lobsters was a true highlight. Their lobster sandwich is a simple yet incredibly delicious gem – so sweet and succulent.
• Later, we met a dear friend from HBS for cocktails at Brick & Mortar, enjoying their amazing drinks and vibrant bar atmosphere.
• Dinner brought us to Basta Pasta, our former go-to neighborhood restaurant. We highly recommend ordering the homemade fusilli Bolognese and their delicious pizza – it was just as fantastic as we remembered.
• We rounded off the day with an ice cream stop at Christina’s, a nostalgic choice, though JP Lick’s still holds the crown for us this trip!

Day 4: Fenway Excitement & Panoramic City Views

• After a leisurely morning, we headed straight to Fenway Park for an exciting Red Sox vs. Astros game. The quintessential family baseball experience was complete with Fenway hot dogs, ice cream served in souvenir helmets, and the incredible opportunity for the kids to run the bases after the game – a moment they’ll cherish forever!
• Following the game, we took a pleasant walk across Harvard Bridge to explore the Massachusetts Institute of Technology (MIT) campus, then enjoyed a serene stroll along the Charles River, which is wonderfully closed to cars on Sundays, making it perfect for pedestrians.
• Our afternoon involved exploring the upscale boutiques and charming brownstones of Newbury Street, marveling at the architectural grandeur of the Boston Public Library, and ascending to View Boston at the Prudential Center. The panoramic views of the city from this observation deck were simply stunning, offering a breathtaking perspective of Boston’s diverse landscape.
• A fun Duck Boat Tour departing from the Prudential Center was a huge hit! The kids absolutely loved the unique experience of driving the amphibious vehicle when it splashed into the Charles River.
• Dinner was a culinary delight at Saltie Girl, where the clam chowder and lobster roll were hands down our favorites of the entire trip, setting a new standard for these classic New England dishes.
• Of course, we couldn’t resist another stop for ice cream (again!) at JP Lick’s on Newbury Street. Our top flavor picks included peanut butter cookies & creme, mint cookies & creme, coffee cookies & creme, and brownie brownie batter. Pure bliss!

Day 5: History, Sports & Waterfront Wonders

• We began our final full day with delicious morning pastries from Tatte Bakery. With numerous locations across Boston, Tatte offers an amazing assortment of pastries and breakfast foods to choose from, perfect for a quick and tasty start.
• Our morning was dedicated to exploring the impressive USS Constitution Ship and Museum, immersing ourselves in naval history aboard “Old Ironsides.”
• Next, we enjoyed a noon tour of TD Garden, home to the Bruins and Celtics, followed by a special stop at CardVault, a sports card shop that thrilled our boys, who are currently obsessed with collecting sports cards.
• Lunch offered us two distinct and appealing options: authentic Dim Sum at Dynasty in the vibrant Chinatown, or incredibly fresh seafood at James Hook & Co right on the picturesque waterfront.
• The afternoon was spent at the interactive Boston Tea Party Ships & Museum. It proved to be a fantastic blend of fun and education, and the kids absolutely loved the highlight of throwing “tea” overboard, reliving a pivotal moment in American history.
• We then enjoyed a leisurely walk along the beautiful waterfront, taking in the sights and stopping to observe the fascinating marine life at the New England Aquarium.
• Dinner brought us back to the North End for Giacomo’s, a classic Italian restaurant we used to adore. While the service was excellent, we were a little disappointed to find the food wasn’t quite as good as we remembered. (Note: Giacomo’s is cash-only and does not take reservations.)
• Our dessert showdown featured pastries from Modern Pastry and Bova’s, but once again, the incomparable cannoli from Mike’s Pastry ultimately won our hearts!

Day 6: A Fond Farewell & Last Bites

• We began our final day with a last, enjoyable stroll and some souvenir shopping along the charming Newbury Street, soaking in the vibrant atmosphere one last time.
• Brunch at Stephanie’s on Newbury was a delightful experience. We secured a beautiful table on the patio, offering a perfect spot for people-watching while we savored our meal. The food surprisingly exceeded our memories, with the mezza platter, lobster roll, and turkey club sandwich being particular favorites.
• Naturally, we couldn’t leave Boston without one more visit to JP Lick’s for a final scoop of our favorite ice cream.
• Our very last activity was a serene walk through the exquisite Boston Public Garden, allowing us to reflect on our wonderful trip amidst its beautiful scenery.
• Finally, it was time to head to the airport, filled with cherished memories and a desire to return.

Essential Tips for Visiting Boston with Kids

• Strategic Planning by Region: To maximize your time and minimize travel fatigue, organize your daily itinerary by breaking the city into distinct geographic regions. This approach allows for efficient exploration and reduces unnecessary back-and-forth travel, making each day flow seamlessly.
• Leverage Google Maps Links: For ultimate convenience, I meticulously added Google Maps links for every single location in our itinerary. This meant we could simply click a link to get instant directions and gather more information about our next stop. I’ve included these valuable links throughout our itinerary above, hoping they will significantly enhance your planning and on-the-go navigation!
• Share Your Itinerary Digitally: Beyond personal use, I created a detailed itinerary with all the Google Maps links in a shared Notes app on my phone, sharing it with Brandon. This ensured both of us could easily navigate. Crucially, I also shared it with our boys. They absolutely loved being able to see the plan, understand where we were going next, and even confidently navigate us from place to place. By the second day, they were enthusiastically leading the way and often anticipating our next activity. Empowering them with this knowledge truly was a “trip changer,” contributing immensely to how amazingly smoothly everything went, as children generally thrive with a clear schedule and understanding of the plan.
• Embrace Flexibility: While having a plan is key, avoid rigid timing for every activity. We purposely didn’t set strict schedules, allowing for spontaneous breaks. We constantly monitored the kids’ energy levels, and whenever they seemed to need a respite from walking or absorbing history, we’d make an impromptu stop at a nearby park or basketball court for some free play, or find a treat to sit and share, ensuring everyone stayed happy and engaged.
• Walk, Walk, Walk (and Enjoy the Scenery!): Boston is incredibly walkable, and we averaged over 20,000 steps per day! However, it rarely felt arduous because there is always something fascinating to do or see at every turn, from historic landmarks to charming storefronts and bustling street life. Comfortable shoes are a must!
• Utilize the “T” (Subway): For distances that are too far to walk or when you need a quick change of scenery, take Boston’s subway system, affectionately known as the “T.” It’s remarkably easy, clean, and a fun experience for the kids, offering a convenient way to navigate the city.
• Indulge in Boston’s Culinary Delights: Do not, under any circumstances, skip the iconic local foods! Make sure to savor authentic cannoli (especially from Mike’s Pastry!), succulent lobster rolls, creamy clam chowder, the classic Boston cream pie, and all the incredible Italian dishes the North End has to offer. And, of course, multiple scoops of ice cream from JP Lick’s are non-negotiable!

This trip truly exceeded all our expectations, proving to be a perfect blend of cherished nostalgia, incredible food, endless fun, and profound historical exploration. Boston confirmed its reputation as an exceptionally walkable, clean, and family-friendly city, and witnessing its wonders through our children’s enthusiastic eyes was an unparalleled joy. The memories we created, especially sharing our old stomping grounds in Cambridge and Harvard Business School, were genuinely priceless and will be treasured for years to come.

xoxo,