Boston Itinerary – 3 Days in Boston for First Timers

In Boston for a brief vacation but unsure how to maximize your time? If you’ve only got 3 days in Boston, we have some great suggestions for what to see and do on your trip.

This Boston itinerary encompasses a wide variety of activities and attractions, so it really helps you to see the best of Boston in a limited amount of time. We’ve also included both indoor and outdoor options, so you can make the most of your trip regardless of which time of year you’re visiting.

This 3 day itinerary includes:

  • Hop-on Hop-off Sightseeing Trolley
  • Fenway Park Tour
  • Skywalk Observatory
  • Freedom Trail Walking Tour
  • Old State House
  • Institute of Contemporary Art OR USS Constitution Cruise
  • Boston Children’s Museum OR Boston Whale Watch Cruise
  • New England Aquarium
  • Mary Baker Eddy Library

Only have a few days in Boston? We’ve also put together a 1 day and 2 day itinerary.

Save on Attraction Admission

Pick up a 3-Day Go Boston® Card and save off combined admission vs paying at the gate.

Remember, this 3 days in Boston itinerary is just one of many ways to experience the area.

The Go Boston® Card gives you the flexibility to create your own itinerary, so you can choose from dozens of top attractions and create a vacation tailored to your interests.


Stop #1: Boston Trolley Ride

This hop-on, hop-off Boston trolley is the perfect introduction to Boston. It will take you all around the city past all the big landmarks and highlights, and is a convenient way to get to some of the major attractions.

Some highlights of your trolley tour include the historic North End, Quincy Market, the USS Constitution and the Bunker Hill Monument, the Theater District and Chinatown, the Boston Public Gardens, and more!

Be sure to pick up your ticket in advance at any of the designated pickup locations. Time on the trolley will vary according to your plans. It can take one to two hours to ride the entire route, depending upon traffic, so keep that in mind when planning your day.

Getting In: Hop On Hop Off Boston Trolley Tour tickets are included on the Go Boston Card.

Stop #2: Fenway Park Tour

fenway-park-tourSports lovers and history fans alike will not want to leave Boston without taking the opportunity to tour Fenway Park, truly a magnificent and historical stadium.

Fenway Park is actually the oldest ballpark in Major League Baseball, so it’s chock full of significant places and people.

Some highlights include the famed Green Monster wall, the Fisk Pole, Duffy’s Cliff, The Triangle, the Lone Red Seat and more! Don’t forget to stop for souvenirs!

Tours run daily between 9:00 am – 5:30 pm, or 3 hours before game time. We recommend leaving at least an hour for this attraction (including time to shop at the team store!)

Of course, taking in a baseball game is always a fun addition to any seasonal vacation. Why not pick up a few tickets while you’re in town?

Getting In: Fenway Park Tour tickets are included on the Go Boston Card.

Stop #3: Skywalk Observatory

Skywalk-Observatory-4After you explore the Fenway area a bit, we suggest heading over towards the Prudential Center area on Boylston Street.

There you can ascend to the top of the Prudential Center for a stop to the popular Skywalk Observatory, with its 360-degree views of metro Boston. Definitely bring your camera to this attraction!

Located 50 floors up in the air, this is actually Boston’s only sky-high vantage point. (The city itself doesn’t have too many tall buildings, either, so you’ll be able to see the lovely historic skyline for quite some distance.)

You’ll also find a number of interactive exhibits and historical displays located throughout the Observatory, so you’ll learn about the buildings you’re seeing below.

We recommend reserving between 30 minutes to an hour for this attraction.

Getting In: Skywalk Observatory Boston tickets are included on the Go Boston Card.


Stop #1: Freedom Trail Walking Tour

freedom-trailAnother must-do Boston attraction, the Freedom Trail Walking Tour is a great on-foot perspective of the city’s historical hotspots.

This guided tour (hosted by actors in eighteenth-century costume!) will also teach you about the stories and secrets of the main figures and significant events of the American Revolution, plus some insider info about Boston’s history as a whole.

You could also opt to walk the red brick line throughout the city without a guide – it will give you more flexibility in time and distance, but without the background info.

Be sure to checkout our post on all the Freedom Trail sites and locations that you will see during your tour.

Tours run throughout the day, but hours vary seasonally and by day of the week.

Getting In: Freedom Trail Boston Walking Tour tickets are included on the Go Boston Card.

Stop #2: Old State House

The-Old-State-House-Museum-1This is one of the stops along the Freedom Trail Walking Tour, but Boston’s Old State House is worth a special shout out in this itinerary.

Explore at your own pace and enjoy tours and performances (every thirty minutes) led by fun, interactive guides or fully costumed Revolutionary characters!

Highlights include John Hancock’s lavish red velvet coat, arms and ammunition from Revolutionary War battles, and tea salvaged from the Boston Tea Party.

Getting In: Old State House tickets are included on the Go Boston Card.

Stop #3: Institute of Contemporary Art (indoor option)

Institute-of-Contemporary-Art-1Art lovers will find much to adore in Boston’s iconic Institute of Contemporary Art, from the gorgeous and distinctive building itself to the astonishing works within.

Home to some of the most cutting-edge work being done in contemporary art across the globe, the ICA features frequent changing exhibitions alongside a well-curated permanent collection to offer only the most thought-provoking and inspiring works of art to visitors.

Located in a completely revitalized waterfront neighborhood in Boston, the ICA is also an excellent stop on a lager itinerary that includes dining, shopping, and other top attractions, so it’s a great component to work into your trip.

They also offer some special programming, so be sure to consult their event calendar before your visit to see if anything interests you! Their gift shop also features both upscale and affordable goods that reflect that modern art aesthetic, so it’s a great place to find presents and souvenirs.

We recommend leaving 2-3 hours to explore the ICA.

Getting In: Boston ICA tickets are included with the Go Boston Card.

Stop #3: USS Constitution Cruise (outdoor option)

Boston-Harbor-Cruise-s-45-Minute-Constitution-Cruise-4Who doesn’t love historic vessels, especially in a waterfront city like Boston?

The USS Constitution Cruise brings you up close and personal with “Old Ironsides” at her home in the Charlestown Navy Yard and allows you the option to disembark for a tour of the famous ship and adjacent Naval Museum.

If you choose not to get off and explore, you can just sit back and relax on this delightful and informative cruise through the Boston Harbor. Either way, it’s a great opportunity for some photos of the iconic Boston skyline!

This cruise is sold on first-come, first-served basis. Tours run seasonally (typically late March through early November) and run multiple times per day, so they are easy to schedule.

Getting In: USS Constitution Cruise tickets are included on the Go Boston Card. Closed during winter months.


Stop #1: Boston Children’s Museum (indoor option)

Boston-Children-s-Museum-5This dynamic, interactive children’s museum is the perfect place for kids to play and learn. All exhibits are designed to make your kids think as they explore, and grow as they engage with unique objects and interfaces.

For example, children love the Art Studio, where they can create to their heart’s content and learn about shapes, colors, tools, and forms while they express themselves artistically.

Another popular area is the New Balance Foundation Climb, a 3-story climbing sculpture that’s part activity, part puzzle, and all fun!

They also offer a wide variety of special programming and unique activities, so be sure to consult their operating calendar before you visit to see what’s going on during your trip. 

Getting In: Boston Children’s Museum tickets are included with the Go Boston Card.

Stop #1: New England Aquarium Whale Watch (outdoor option)

New-England-Aquarium-Whale-Watch-2This cruise will take you out into the Atlantic Ocean to the Stellwagen Bank Marine Sanctuary, home to giant marine mammals including various species of whale and dolphin.

You’ll also see a number of sea birds and other marine life, but the highlight is going to be the potentially wide variety of whales that you may encounter.

Species of whales in the neighborhood include humpback whales, finback whales, and minke whales. If you have a video camera or a phone capable of taking video, we recommend bringing it along on this cruise.

We do recommend making reservations in advance, and be sure to mention that you have a Go Boston Card while making reservations. Arrive at least 30 minutes before your cruise time; the cruise will take at approximately four hours.

Getting In: Boston Whale Watch tickets are included as an option on 3, 5, and 7-Day Go Boston Cards

Stop #2: New England Aquarium

new-england-aquariumThe New England Aquarium is bound to be a favorite with the kids, and adults will find so much explore as well!

The four-story Caribbean coral reef is one of the most popular exhibits, filled with tons of tropical fish and other exotic creatures.

Be sure to visit the Shark and Ray Touch Tank and take the opportunity to interact with those fascinating creatures. And don’t forget about the Aquarium’s stars – the lovable, goofy penguins!

There’s also a delightful IMAX movie available onsite (rotating regularly), which comes at a small additional cost.

Since there’s so much to see and do here, we recommend reserving at least two hours for this attraction.

Getting In: New England Aquarium tickets are included on the Go Boston Card.

Stop #3: Mary Baker Eddy Library (indoor option)

The-Mary-Baker-Eddy-Library-Mapparium-1Another excellent place for the family to expand their minds is the Mary Baker Eddy Library and Mapparium. This attraction offers the resources and exhibits of a research library alongside the fun and excitement of an interactive museum.

Visit everything from the Hall of Ideas (where you can follow an interactive exhibit that traces inspirational quotes from historical figures) to the Quest Gallery (which focuses on the life and times of Mary Baker Eddy herself).

Don’t forget about the stunning Mapparium! This massive painted glass globe illustrates the circulation of knowledge throughout the globe with colored lights and shapes.

Honor a woman who fought for education and for women’s rights in the nineteenth century with a visit to this fascinating attraction. 

Getting In: Mary Baker Eddy Library and Mapparium tickets are included with the Go Boston Card.

Stop #3: Swan Boat Ride (outdoor option)

The-Swan-Boats-of-Boston-1The Boston Swan Boats are among the most iconic characters in the city.

The pond and the boats are found in Boston’s gorgeous public gardens, which many Bostonians consider their favorite part of the city.

Made famous in stories like Make Way for Ducklings and The Trumpet of the Swan, the Swan Boats are the only vessels of their kind in the world.

Ride on this historic vessel with your sweetheart or your friends, and enjoy the opportunity to soak up the beauty of the surrounding gardens.

Getting In: Swan Boats of Boston tickets are included on the Go Boston Card.

Let’s Recap

So there’s a local’s suggestion for how to spend your three days in Boston. It’s an itinerary that’s jam-packed with everything that a first time visitor to Boston really shouldn’t miss.

If you visit these included attractions with your 3-Day Go Boston® Card, you’ll save big off combined admission cost vs. paying at the gate. You’ll also be able to enjoy select extra discounts on shopping and dining options with your pass.

Go Boston Card

The information contained in this post, to the best of the author's knowledge, was accurate at time of publishing. We do our best to ensure and maintain the accuracy of this information.


  1. Nancy P. King says

    Informitive site. I dont feel like im going to boston blind and I think the little walking tour will fit just right.

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