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5 Days of Family Summer Fun in Boston

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Let me start by saying that I absolutely love Boston.  Growing just outside Boston as a kid it still runs through my veins!  As a die-hard Celtics and Red Sox fan now living in warmer climates, I can’t resist returning with my family to my favorite summer city—Boston. This 5-day family adventure dives into the heart of Beantown’s magic, from the American Revolution’s historic Freedom Trail to world-class museums, the New England Aquarium, Harvard’s ivy-covered campus, and iconic spots like Quincy Market, Faneuil Hall, and the U.S.S. Constitution. Oh, and don’t forget the creamy chowda! Grab your kids and let’s explore the city that’s got it all for an unforgettable summer escape!
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Let's Start with the Basics - Where to Stay

Let’s kick off your Family Summer Adventure in Boston the right way. Picking the perfect spot to stay is key to a smooth trip. 

My go-to with kids is Back Bay, roughly between Copley Square and the Public Garden. Why here? It’s central, packed with restaurants, and steps from the T (Boston’s subway) for easy access to downtown and Cambridge. Plus, it’s got those gorgeous brownstones that make you feel like you’re in a history book.
 

Where to Stay: For my family, I love mid-range hotels with breakfast included.  It’s an easy way to fuel up for fun days and makes me feel better that I didn’t spend $20 on pancakes that my 9-year-old just looked at.  On our last trip to Boston we stayed at the Residence Inn by Marriott Boston Back Bay/Fenway.  It was near Fenway Park which was convenient for game day, but hit the highlights for the kids: excellent breakfast and a rooftop pool!

If you’re not as hung up on the free breakfast as we are, there are lots of other great options.  One of the well located spots we also like is the Hotel Indigo Boston Garden by IHG.  This one is great because it’s a 15ish minute walk to many of the Boston attractions: Boston Common, Faneuil Hall, Freedom Trail, New England Aquarium and Museum of Science.

 

Special Occasion:  Splurge at the Fairmont Copley Plaza (138 St James Ave), a historic gem opened in 1912 with elegant rooms and a prime spot near Copley Square. It’s not cheap, but the old-world charm and proximity to the Boston Public Library make it a treat for families wanting luxury.

Flying In?

From Logan International Airport to Back Bay

Logan, just 4 miles from Back Bay, is a quick trip. A taxi costs $25–$35 (including $2.75 airport fee and $2–$5 tolls, plus 20% tip), taking 15–30 minutes depending on traffic. Uber/Lyft averages $20–$35 (UberX) or $30–$45 (UberXL for families with luggage), also 15–30 minutes, but watch for surge pricing. For a budget-friendly option, take the Silver Line SL1 bus (free from Logan) to South Station, then the Red Line T to Park Street and transfer to the Green Line for Back Bay ($2.40/ride); it’s $2.40/adult, about 30–45 minutes. Taxis or Uber are easiest with kids and bags, but the Silver Line saves cash for extra lobster rolls. 

Want a Rental Car?  For most of the Boston trip, you are better off with taxis, Uber and Lyfts and the T.  However if you’re planning to hit sites outside of the city, a rental car is your best bet.  Instead of getting the car from the airport, you may want to wait to rent just for the day for day trips instead of trying to drive around Boston and find expensive parking.  Get your Rental Car – Expedia.com

Flight Essentials

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When to Go?

Summer is my top pick for a Family Adventure in Boston, with warm days (mid-70s to mid-80s °F) perfect for strolling the lush Boston Public Garden, picnicking in Boston Common, and cheering at a Red Sox game at Fenway Park. The city buzzes with festivals and outdoor fun, ideal for kids. 

That said, Boston’s holiday season is magical, with twinkling lights, ice skating on the Common, and festive vibes at Faneuil Hall, making it a cozy winter escape.

 
For your trip use our free Packing Tool for a tailored list based on your activities and the latest weather.
 

Day 1 -Settling In and Exploring

Afternoon

We arrived at Logan Airport just after 12PM, so after finding our bags we head to the Residence Inn by Marriott Boston Back Bay/Fenway via Uber which was about a 30 minute trip.  Luckily we were able to check in and settle into the hotel’s suite, where the kids picked their spots.  We set up all of the chargers, unpacked a bit, shook off the airport and were ready to get started.

Our Family Summer Adventure in Boston began with a short stroll to explore the vibrant Fenway area. The Red Sox were at home this week and even though game time wasn’t until later, Boylston Street was already buzzing.  Seeing Fenway Park is like stepping back to 1912 when it was opened.  It’s changed some, but not much.  We decided to walk toward the Boston Public Garden, which was a beautiful walk past old brownstones and some boutique shops along Commonwealth Avenue.  It took about 15 minutes and it was cool to see all of the huge trees and flowers and lagoon where the Swan Boats were roaming.  By late afternoon it we head back toward the hotel.  Lots of others, seemingly headed to tonight’s game, were headed with us.  Is there tailgating in baseball?  

Evening

For dinner, we walked to Citizen Public House & Oyster Bar, a vibrant spot that felt like Fenway’s heartbeat. I couldn’t resist their smoked pork belly tacos, a melt-in-your-mouth specialty that paired perfectly with a local IPA. The kids devoured mini sliders and creamy mac and cheese, chattering happily in the warm, wood-paneled dining room filled with locals and fans. The friendly vibe made us feel right at home.
Back at the Residence Inn, we let the kids splash in the hotel’s indoor pool, there were some other kids there which made for a fun time.  If you asked them, the pool was their highlight of the first day.

Day 2 - Freedom Trail, Quincy Market, and Aquarium Fun

Morning

I woke up in our cozy suite at the Residence Inn by Marriott Boston Back Bay/Fenway, grateful for the included breakfast buffet that had my kids piling their plates with waffles and fruit while I sipped strong coffee. Fueled up, we set off to dive into Boston’s history, which I worried might bore the kids, but boy, was I wrong! We walked about 15 minutes to the Boston Common Visitor Center for a costumed Freedom Trail tour (booked at thefreedomtrail.org, ~90 minutes). Our guide, decked out in 18th-century garb, had my kids hooked with lively tales of the American Revolution, leading us through Boston Common, America’s oldest park; the Old Granary Burying Ground, where Paul Revere rests; and the Old State House, marked by a cobblestone circle for the Boston Massacre. Their eyes were wide, giggling at the guide’s dramatic flair.

Lunch

After the tour, we strolled about 5 minutes to Quincy Market, a vibrant food hall buzzing with energy. We grabbed creamy clam chowder from Boston Chowda—a New England classic—and the kids devoured slices from Regina Pizzeria, topping it off with ice cream that had them beaming.

Afternoon

Powered up, we walked about 10 minutes to the New England Aquarium, where my kids were mesmerized by the four-story ocean tank teeming with sea turtles and colorful fish. Aquariums seem to be one of our favorites and this one was impressive.  We spent around 2 hours lost in the underwater wonderland.
 
TIP: Get the Boston CityPASS tickets ($79 adult/$69 kids 3-11) it covers the Aquarium, Science Museum, Boston Harbor City Cruises plus the Harvard Museum of Natural History. 

Dinner

We wandered about 7 minutes from the New England Aquarium to Ristorante Euno  in the North End, Boston’s Little Italy. I savored their chicken parmesan, a golden, cheesy masterpiece, while the kids twirled spaghetti and meatballs in the cozy, brick-walled dining room.   We decided to diverge from our typical ice cream run, to try a Boston favorite – cannolis from Mike’s Pastry.  It did not dissappoint.

Evening

After dinner, we roamed the North End’s charming streets, soaking in the Italian vibe with gelato shops (yes, we tried some) and twinkling lights. Ready to get off our feet, we hopped on the Green Line T from Haymarket (about 5-minute walk, $2.40/adult, kids under 11 free with an adult) back to the Residence Inn (~10-minute ride).  Somehow, the 10-minute subway ride rejuvenated the kids enough to hit the pool again.  They burned their last bit of energy and we all crashed hard that night.

Day 3 - USS Constitution, Boston Common, and Red Sox Fever

Morning

We loaded up on the free breakfast buffet had my kids loading up on pancakes while I fueled up with coffee for another history-filled day. We hopped on the Green Line T (10-minute ride) to the North End for a morning visit to the USS Constitution (1 Constitution Rd, about a 5-minute walk from North Station). Nicknamed “Old Ironsides,” this 1797 warship, the world’s oldest commissioned naval vessel still afloat, had my kids wide-eyed as we explored its decks and cannons. The free guided tour (30 minutes, donations appreciated) brought Revolutionary War stories to life, and the kids loved learning how the ship’s sturdy oak hull earned its nickname by repelling cannonballs.

Lunch

We took the T back to Park Street (~10-minute ride) and walked about 5 minutes to Boston Common, where we enjoyed a picnic lunch with sandwiches from Sam LaGrassa’s. Sprawled on the grass in America’s oldest park, the kids ran around near the Frog Pond, soaking in the sunny summer vibe while I relaxed under the shade of ancient trees.

Afternoon

After lunch, we strolled about 15 minutes back to the Residence Inn by Marriott Boston Back Bay/Fenway (125 Brookline Ave), passing charming Back Bay brownstones. We took some time to chill in our suite, letting the kids play games or nap to recharge for the evening’s big event.

Dinner

Back at the hotel, we grabbed a quick, kid-friendly dinner at the nearby Tasty Burger, where I savored a juicy Star Burger with tangy sauce , and the kids munched on cheeseburgers and fries, loving the casual, retro diner vibe just steps from Fenway.  If you go on a game day – go early. It fills up quickly.

Evening

We walked just 4 minutes to Fenway Park for a Boston Red Sox game, (check mlb.com/redsox for schedules). The electric atmosphere of America’s oldest ballpark had us all cheering.  By the 4th inning, somehow the smell of hot dogs had us hungry again, so the kids got the famouse Fenway frank and I went for Sweet Italian Sausage.  I’m not sure if it was the atmosphere, but they seemed like the best ever.
 
We even made to the 7th inning and got to sing the full chorus of “Sweet Caroline”.  Try the sausages and munching overpriced hot dogs and sausages. The kids were thrilled watching the Green Monster in action, and I couldn’t help but feel that old Beantown pride swell. After the game, we wandered back to the Residence Inn (4-minute walk), the kids still buzzing from the crowd’s energy.  It was way past their bedtime (and mine), but totally worth it.  

Day 4 - Science and Duck Boats

Morning

I woke up at the hotel feeling the effects of last night’s Red Sox game—those “Sweet Caroline” sing-alongs took it out of us! The kids were sluggish, so we lingered over the free breakfast buffet, piling plates with waffles while I sipped coffee to shake off the fog. After some lounging in our cozy suite, we rallied and took the Green Line T (~10-minute ride) to the Museum of Science. The kids lit up at the T-Rex skeleton and went wild for the Lightning Show, while the interactive space and engineering exhibits kept us hooked for hours. Our Boston CityPASS covered entry.
 
Tip: The electricity show is loud and could be upsetting to young children.  It is amazing though.

Lunch

We stayed at the Museum of Science for lunch at the Galileo Café (inside the museum), where the kids munched on kid-friendly pizza and chicken tenders, and I grabbed a hearty sandwich, all in a casual, family-oriented spot with views of the Charles River. It was quick and kept us fueled for the afternoon.

Afternoon

Right outside the museum, we hopped on a Boston Duck Boat Tour (booked at bostonducktours.com), an 80-minute amphibious ride that cruised through Boston’s streets and splashed into the Charles River. The kids giggled as our guide quacked and shared fun facts, pointing out landmarks like the State House and the river’s shimmering skyline.  Maybe it was because I was glad to sit down, but I really enjoyed the Duck Boat Tour.

Dinner

We took the Green Line T (10-minute ride) to Park Street and walked about 5 minutes to Boston Common, settling into The Cheesecake Factory for a kid-friendly dinner. Their menu is practically a novel, so there’s something for everyone.  I savored their creamy chicken madeira, a house favorite, while the kids loved the crispy chicken fingers and pasta in the lively, family-packed dining room.  We did skip the cheesecake, in hopes of some gelato later.

Evening

After dinner, we wandered Boston Common, people-watching as street performers juggled and locals jogged by. The kids (and me) were hunting for for ice cream, so we stopped at Emack & Bolio’s for creamy scoops of their famous Grasshopper Pie flavor. It was another 15-minute walk back to the Residence Inn but it was a beautiful evening.  After another full day, we kicked back in our suite for a family movie night, snuggled up with popcorn, laughing and relaxing before our final Boston adventure.

Day 5 - Pool Day and Farewell

Morning

We got off to an early start, maybe because our departure was looming and we didn’t want to miss out.  Check-out was set for 11 AM, but I asked the front desk for an extension, and they kindly pushed it to 12 PM.  (Tip: Just ask, and they’ll often accommodate.)

We’d tossed around ideas like hitting the Harvard Museum of Natural History or chilling at Boston Common, but the kids begged for more time in the hotel’s indoor pool. Honestly, after our jam-packed days, a lazy pool day sounded perfect. So, we spent the morning splashing and laughing in the pool, the kids doing cannonballs while I lounged nearby, soaking in the relaxed vibes.
 

The morning went quickly and soon it was 12 PM – Time to head back to the airport.  We said goodbye to Boston, hopping in a taxi to Logan Airport for our afternoon flight. As we drove away, the kids chattered about their favorite moments—Fenway’s energy, the Aquarium’s penguins—and I felt that familiar Beantown tug, already planning our next visit.

 

Adventures We Missed

Our 5-day Boston adventure was a blast, but there were a few gems we didn’t squeeze in, and I’m already itching to come back for them! The Seaport District, with its modern vibe, Lawn on D’s glowing swings, and the Institute of Contemporary Art, was high on my list for its family-friendly fun, but we ran out of time. The Harvard Museum of Natural History in Cambridge, with its dinosaur skeletons and stunning glass flowers, was another miss—my kids would’ve loved it. We also skipped the Boston Tea Party Ships & Museum, where you can toss tea overboard like a Revolutionary, and the Isabella Stewart Gardner Museum, a Venetian-style palace with jaw-dropping art. These big ones are calling my name for our next Beantown trip, and I’d love to hear what you’d add to your Boston list—drop a comment!

Want More? Check Out These Family Itineraries.

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