The perfect 2 day Boston itinerary for families

The Ultimate 2 Day Boston Itinerary For Families

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Are you wondering how to spend 2 days in Boston? Boston is famous for its incredible and jaw-dropping scenery. A trip to Boston ensures an unforgettable experience for you and your family.

However, before visiting Boston, it is essential to outline the major elements of your trip. Usually, visiting most of the tourist attractions in Boston requires at least a two-day trip, therefore to help you plan the ultimate getaway, we are sharing with you the perfect 2 day Boston itinerary for families, so you can make the most of the city with or without kids.

The following Boston weekend itinerary is a guest post by Via Travelers, a modern travel blog focused on helping you learn the best travel tips, hacks and itineraries to travel the world.

This hop on hop off trolley tour is a fun way to see Boston

The perfect 2 day Boston itinerary for families


A weekend may not seem like a lot of time to experience a city, however, there is a lot you can fit into 48 hours.

Our goal with this Boston travel guide is to help you maximise your time to see all the must-see Boston tourist spots. To assist you, we have created the perfect 2 day family itinerary for Boston.

By keeping these suggestions in mind, you can enjoy your vacation and see much of this incredible city.

Day 1 of Visiting Boston

To make most out of Boston in 2 days, try to visit the maximum number of tourist attractions on your first day. Some of the top suggestions are listed below to help you prioritise which you don’t want to miss.

Take a Bus Tour of Boston

The bus tour is a great way to see most of the popular tourist attractions on day one. Especially, if visiting Boston with kids.

A hop on hop off trolley tour is a great option if you don’t have your own transport, or if you want to avoid navigating your way around an unfamiliar city on your first visit. Riding the Old Town trolley is a great novelty for the whole family too.

Visit the Mapparium

There is nothing cooler than walking through a giant globe. The Mapparium is a massive globe made of glass and metal structure. This marvellous piece of architecture is within the Mary Baker Eddy Library.

This art installation allows you to witness the earth from a whole new perspective. It serves as a great spot to help kids learn the basics of the world’s geography.

Visit the Boston Common

Boston Commons - Boston weekend itinerary

Boston Common is one of the most amazing and classic places in Boston. This huge parkland is a perfect place to have a picnic. Kids love this place, as there is a lot of space to run and play.

If you are visiting Boston with kids, this is the best place to hang out for a while and let them run off some steam.

Adjacent to Boston Common you will find Boston Public Garden also.

Need help planning your next family vacation? Check out our FAMILY TRAVEL GUIDE

Feast at North End

North End is the Italian Quarter, where you can enjoy a delicious pizza and other authentic Italian cuisines. You will easily find a great place to grab lunch, as there is a variety of famous Italian restaurants and bakeries in the area.

Why not try a North End pizza tour for lunch?

Walk the Freedom Trail

The Freedom Trail is a 2.5-mile stretch, which guides you toward 16 historical sites. It’s a beautiful red brick path. The best time to walk on this trail is in the afternoon. A full tour of this trail takes almost a day.

Hence, less time would be left to visit other attractions. You see a lot when you book this tour and it’s a great value for the price.

Or for a tour with a twist, add a foodie element to your Freedom Trail tour, or if you are kid-free, consider a pub crawl or ghost tour after dark.

Some of the most recommend historical sites include:

  • Massachusetts State House
  • Park Street Church
  • Granary Burying Ground
  • Benjamin Franklin Statue and Boston Latin School Site
  • Old Corner Bookstore
  • Old South Meeting House
  • Boston Massacre Site
  • Paul Revere House
  • Old North Church
  • Bunker Hill Monument
  • Boston Public Library
  • Old State House

Take a Relaxing Boat Ride

2 day boston itinerary for families

To relax and unwind your body after walking the long freedom trail, enjoy one of the sunset cruises, such as Boston Harbor sunset sails. This boat tour may turn out to be the best part of your two-day visit to Boston.

This narrated boat tour continues for 90 minutes, which relates to the history of Boston Harbor. You can buy beverages and food on the cruise in case you’re feeling peckish after your big walk.

It’s a fun activity to enjoy with your family after a fun day in Boston.

To mark its end of the day, the USS Constitution (US Battle Ship) fire their cannon. Witnessing this amazing moment is one of the Boston highlights not to be missed.

Day 2 of Ultimate Boston Itinerary


After having a good night sleep, start your second day with a delightful breakfast. The Day 2 of your ultimate trip to Boston itinerary involves the following routine.

Visit the New England Aquarium

Adults and kids with both love the Boston aquarium, offering a wonderful insight into the vastly diversified marine life.

The New England Aquarium is located close to the Faneuil Hall and Quincy Market. It’s a perfect chance to witness marine life up close.

The aquarium is a four-story giant tank with large viewing windows. Here you can watch a variety of Caribbean coral reef animals like stingrays, fishes, eels, and sea turtles. Penguins and sharks are among some other exhibits.

If you want a whale-watching experience, you can book a tour online and have the chance to see whales in their natural environment.

Head to TD Garden Sports Museum

Visiting the TD Sports Museum is a perfect way to learn about the history of sports. If you have perfectly planned your day 2, it would be easy for you to accommodate this place in your two-day Boston itinerary.

If you are a Boston fan, visiting this place is a must. The guided voice tour lasts for one hour, incorporating all the essential elements of Boston sports era.

The display of legendary exhibits and artifacts is a treat for sports enthusiasts.

Boat cruise Boston

Take a Swan Boat Ride

Swan Boats are the iconic part of your two-day Boston itinerary. Riding these boats is an ideal option if you prefer a low-key cruise. When paddling your Swan Boat, you will come across the Public Garden lagoon, which is in close vicinity to Boston Common.

These boats originated in the year 1877 and form part of historic Boston. Even after passing through four generations, the boats are still under the ownership of the same family.

Hence, when riding these boats, you are reliving history. Plus the kids will love the experience!

Take a Tour of Samuel Adams Brewery

When feeling a bit tired, head to the Samuel Adams Brewery for a slower-paced experience. This place is an ideal option to quench your thirst with some adult beverages. There are four different tours offered by the brewery.

You can take one or more depending on the time you have. To taste the prime quality beer, you need to be 21 years of age.

Tours are available six days a week except for Sunday. Or for the real beer enthusiasts, take a multi brewery tour around the city and sample Boston’s best beers and ciders.

Go to the Skywalk Observatory

Boston skywalk

For a beautiful and charming 360-degree view of Boston’s skyline, there is no better option than visiting the Skywalk observatory. This observatory stands as high as 700 feet.

This massive structure is lying in the Prudential Center on Boylston Street.

Why not dine at one of Boston’s oldest restaurants? Union Oyster House is a Historic eatery that serves up chowder & other New England seafood dishes since 1826.

Got 3 Days In Boston Or More? 

There is more than enough to see and do around Boston to fill in a longer visit if you have the time. Here are some other fun things to do in Boston with kids to help you plan your longer stay in the city:

How To Save Money in Boston

Go City (Boston)

Cut costs during your Boston mini-break or extended vacation by getting a Boston Pass during your visit.

The Boston Pass gives you included admission into over 40 Boston attractions, and tours, including many of the ones recommended in our 2-day itinerary for Boston. You also get additional discounts off dining and shopping around the city too.

Boston Pass will save you up to 55% off the price of attractions and is a great option if you plan to visit several of those included. Find the full list right here.

Check prices for the Boston Pass online

Where To Stay In Boston

If you are headed to Boston for a weekend or staying for a week, you will need a great place to stay. Somewhere central will make it easy for you to get around. Find our recommendations to suit every budget:

Getting Around In Boston

Whether you’re visiting Boston for business or pleasure, you’ll find that getting around the city is a breeze. Boston is served by an extensive public transportation system that includes buses, trains, and subways. If you’re driving into the city, there are several options for parking.

If you’re coming into Boston from out of town, the best way to get around is by using the MBTA, also known as the T. The T is the city’s public transit system and it includes buses, trains, and subways. You can purchase a pass at any T station or at select retailers.

You can also get around Boston by walking or biking. Boston is a very walkable city, and it’s also bike-friendly. There are several bike paths throughout the city, and you can also rent a bike from one of the many bike-sharing stations.

Flying in from elsewhere? You can easily grab a rental car from Logan Boston International Airport for your 2 day itinerary or take public transport to your accommodation.

Search for a rental car here:


We hope this Boston itinerary with kids helps you plan your perfect Boston family trip!

FAQs For Visiting Boston With Kids

Is Boston worth visiting?

Absolutely! Boston is a vibrant and historically rich city that offers a unique blend of culture, history, and modern attractions. From the Freedom Trail to world-class museums, iconic landmarks, and a thriving food scene, there’s something for everyone in Boston.

How many days do you need in Boston?

To fully experience the highlights of Boston, it’s recommended to spend at least 2 to 4 days in the city. This will allow you to explore popular attractions, immerse yourself in the history and culture, and savour the local cuisine.

Is Boston good for families?

Yes, Boston is a fantastic destination for families. With its many parks, museums, interactive exhibits, and family-friendly attractions and outdoor spaces.

Author Bio: Kyle is the Co-Founder and Editor of Via Travelers. Via Travelers is a modern travel blog focused on helping you learn the best travel tips, travel hacks and itineraries to explore the world. Find your wanderlust. Follow them on Instagram and Twitter.

Are you heading to Boston soon? Let us know what’s top of your list of Boston attractions and experiences! You can find more USA travel inspiration and don’t forget to save this post for later! 

The perfect 2 day Boston Itinerary