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2 Days in Boston: A Complete Itinerary to See Everything

2 Days in Boston: A Complete Itinerary to See Everything

Boston is a city that is full of history and culture. If you are time-constrained, that’s okay. Boston is a smaller, dense city with good transportation. Here’s a full itinerary to ensure you see everything you need during your 2 days in Boston.

How to Design the Best 2 Days in Boston Itinerary

When I lived in Boston as a teenager, I never took the opportunity to see all the historical sites. Full disclosure: I didn’t really experience any of them.

Unless you count transportation: taking the T (subway), walking by Harvard, or driving by Fenway.

So was excited to experience what I missed when my family and I visited Boston recently.

If you’re short on time, here are the best 2 days in Boston itinerary that you can customize – as well as some helpful travel tips.

Time-Saving Tips for Your 2 days in Boston

Before you go: Order a Go Boston Pass online

Maximize your time and your savings with a Go Boston All-Inclusive Pass. The pass offers unlimited admission to 40+ Boston attractions, shows, and tours, and you can skip the line for many of them (some of which are included in this post). This is a huge benefit if you only have 48 hours in Boston.

All you do is scan your digital pass to enter – no physical card is required.

You can purchase a one-day pass or save even more with a two-day pass (they offer up to seven-day Go Boston passes with increasing discounts).

There are some other great alternatives to a Go Boston pass that could also save you money on the city’s top attractions. Here’s how it looks versus the competition:

Boston Passes Compared

Boston CityPASS

Boston CityPASS

  • Great value for money
  • Easy to use
Go City logo

Go City - Boston All Inclusive Pass

  • Flexible pass options
  • Savings at 40+ attractions
Go City logo

Go City - Boston Explorer Pass

  • Valid for 1 month
  • Skip the line

Manage expectations on what you can realistically cover in 48 hours in Boston

You simply will have to prioritize what is most important to you.

Boston offers so many incredible experiences for the entire family that it can be easy to overextend yourself and others traveling with you.

So I recommend consulting with your traveling party members to pick and prioritize only two or three must-see activities per day and allow some flexible time in your schedule to create the best 2-day itinerary for Boston so you can all fully enjoy your vacation.

In fact, I would recommend focusing on the Freedom Trail and then, if time and energy (and your wallet) allow, take in some of the other recommendations.

48 hours in Boston Itinerary Options – Day 1

Let’s get started on your first day in Boston to see everything.

Hop-on, hop-off trolley/bus OR motorcoach (chartered bus) tour of Boston

I’m a little directionally challenged, so always like to take a hop-on, hop-off tour on the first day of any new city.

This way I get acclimated to where things are, take in a little history, and get some local tips from the guide. For example: what to see in Boston, things to do in Boston, and/or where to eat in Boston.

I typically don’t take a motorcoach tour as I prefer the freedom to hop off at places that interest me. However, a motorcoach tour is a great option if members of your traveling party are very young or have limited mobility.

You also have the option of using Boston’s easy-to-navigate subway system (Massachusetts Bay Transportation Authority or MBTA) to get from one place to another quickly.

See Related: Do You Need a Car in Boston?

Freedom Trail walking tour

I’m a big fan of the walking tours – both guided and self-guided – as I love to immerse myself into neighborhoods.

My family’s main goal during our short trip to Boston was to walk the Freedom Trail. It’s a 2.5-mile walk that guides you along 16 historical sights via a red brick path.

You could possibly do all this in an afternoon (if you’re super committed and fast), but recommend at least a full day, if not two, depending on your walking pace and the time you allow at each historical location.

  • Travel tip: The trail features cobblestones, bricks, and uneven terrain, so wear comfortable walking shoes (flip flops not a good idea). And bring sunscreen and a rain jacket and/or umbrella as you’ll be outdoors most of the time. We got caught in a few downpours, so was happy we brought our rain gear.
  • Plan ahead: To make the most of your 48-hours-in-Boston vacation, visit the Freedom Trails Foundation website and/or the Freedom Trail visitor information centers for maps, available tours, and more.

Here’s a brief overview of the 16 Freedom Trail historic sites to help you determine which ones you’d like to experience.

  1. Boston Common is the most popular place to start your walking tour – and where you can find the Freedom Trail visitor information center. Centers are also located in Faneuil Hall and the Charlestown Navy Yard.
  2. But it’s not required to start in the Boston Common. We were staying with a friend and arrived via commuter rail at the North Station so started following the red brick path nearby (after we deviated from our original agenda since it was raining and decided to tour the TD Sports Museum first – will share more in the 48 hours in Boston Day 2 section).
  3. Massachusetts State House: If you love architecture along with history, take a free guided tour of the state capitol on weekdays. Definitely some beautiful photo ops here in the Beacon Hill neighborhood.
  4. Park Street Church: Built-in 1809 with a 217-ft. steeple, the Park Street Church was the tallest structure in Boston for many years. The church also established one of America’s first Sunday School programs, which gave working children an opportunity to learn how to read.
  5. Granary Burying Ground is the final resting place of many historical figures, including Paul Revere, Samuel Adams, and the Boston Massacre victims. More than 5,000 are reported to be buried in this location (even though the gravestone markers are considerably fewer).
  6. King’s Chapel & Burying Ground: New England’s oldest church dates back to 1686 and houses the oldest pulpit still in use. The historic cemetery is the final resting place for John Winthrop, first governor of Massachusetts, and Mary Chilton, a Mayflower passenger and Pilgrim, who was believed to be the first European woman to step onto the soil of what is now known as Plymouth, Mass.
  7. Benjamin Franklin Statue and Boston Latin School Site: This historical site marks where the first public school once stood. Franklin attended classes here and at another school for only two years before he dropped out as a child to work in his family’s candle and soap-making business.
  8. Old Corner Bookstore: I love old bookstores with a history, and this meets that criteria. Built in 1718, this location published the works of literary greats such as Henry David Thoreau, Louisa May Alcott, Ralph Waldo Emerson, and Mark Twain.
  9. Old South Meeting House: This is where 5,000 Bostonians gathered in 1773 to protest a tax and start a revolution resulting in throwing hundreds of crates of tea into the Boston Harbor. Nearby is the Boston Tea Party Ships and Museum, which is worth a visit.
  10. Old State House: This meeting place is the location of the 1770 Boston Massacre and where colonists first heard the Declaration of Independence.
  11. Boston Massacre Site: You’ll find this historical site marker at the corner of State and Congress Streets, just outside the Old State House.
  12. Faneuil Hall: This shopping, dining and entertainment complex was originally an open forum meeting hall and marketplace during the Colonial period.
  13. Paul Revere House: You can tour the inside of where Paul Revere and his family once lived; it’s the oldest structure still standing in downtown Boston.
  14. Old North Church: Boston’s oldest church (built in 1723) is where two lanterns were hung to alert Patriots that the British were coming. Paul Revere’s statue immortalizing his historical ride is nearby.
  15. Copp’s Hill Burying Ground: More than 10,000 people, including merchants, artisans, free blacks, slaves and craftspeople, were laid to rest here between 1659 and the 1850s.
  16. USS Constitution: Old Ironsides is the oldest U.S. Navy warship still in commission. You can board the ship and go down below to the lower decks. This site also includes a small museum, and they even offer cruises around the harbor.
  17. Bunker Hill Monument: A 221-ft. obelisk marks the first major battle of the American Revolution, which looks very similar to the Washington Monument. If you’re wanting to get more steps in, you can take 294 stairs to reach the top of the Bunker Hill Monument.
Paul Revere House (1)
Paul Revere House

See Boston by sea

If you’re looking for a great way to unwind and relax after a long day of walking, check out one of the many Boston Harbor sunset sails as part of your 2 days in Boston itinerary.

We did not have the opportunity to take one personally, but I booked Boston Harbor Cruises’ sunset sightseeing cruise for one of my clients recently.

The entire family loved the 90-minute narrated tour, where they learned the history of Boston Harbor and witnessed the USS Constitution fire her cannon to signal the end of the day.

While dinner is not included on this cruise, there are food and beverages available to purchase.

See Related: Best Day Trips from Boston

Day 2 of Your 48 Hour Boston Itinerary

Let’s start off on the second day of your Boston itinerary.

Freedom Trail

Pick up where you left off yesterday if you didn’t get the opportunity to see everything you wanted to experience.

Consider using one of these top sites for booking tours to finish off any other experiences you want.

TD Garden Sports Museum

We lucked out in that we were able to tour the TD Sports Museum (and a small part of TD Garden – home of the Boston Bruins and Boston Celtics) earlier this year.

The TD Garden is undergoing renovation so is closed to tours until the summer of 2020; but the Sports Museum will reopen in October 2019.

If your plans accommodate that timeframe, highly recommend taking this tour even if you’re not a Boston fan (we’re Minnesota Vikings and Minnesota Wild fans).

You’ll learn so much about sports history and see a half-mile of legendary artifacts and exhibits up close during the one-hour tour.

See Related: Best Travel Credit Cards to Consider

Boston Harbor day cruise

If you were too tired to take a sunset cruise, consider sailing around the harbor during the day.

Many tour operators offer different experiences such as a historical tour, brunch tour or whale watching; or you can set sail on a yacht, schooner or even the USS Constitution.

Swan Boats

If you’re looking for a low-key cruise, take a ride on the iconic Swan Boats as you get peddled around the Public Garden lagoon located near Boston Common.

The origin of the Swan Boats dates back to 1877 – and the company is still owned by the same family four generations later.

See Related: Best Travel Credit Card Deals

New England Aquarium and/or Whale Watch

Second only to the ocean, aquariums are my favorite place to reflect and recharge. Located near Faneuil Hall and Quincy Market, you can see marine life up close.

The four-story giant ocean tank alone features large windows where you can watch hundreds of Caribbean coral reef animals, including sea turtles, stingrays, eels, and fishes.

Exhibits also include sharks, penguins, and more. And this is where you can purchase tickets for a whale-watching cruise.

Skyline of Boston, Mass at Dusk
The skyline gives a good look at dusk

Why not check out Martha’s Vineyard or one of the many amazing islands outside of Boston?

Skywalk Observatory

Take in 360-degree views with an audio tour of Boston’s skyline and landscape from 700 feet up in the Prudential Center on Boylston Street (the 50th floor).

Open daily from 10 a.m. to 10 p.m. in the summer and until 8 p.m. in the winter.

Samuel Adams Brewery

If you’re feeling parched and in need of some adult beverages, take a tour of the Samuel Adams Brewery – named after one of America’s founding fathers.

Or take more than one as they offer four tours in all. Tours offered every day except for Sunday, and you must be 21 for the tastings.

See Related: Travel Hacking 101

2-days in Boston itinerary: Where to Eat

2 Days in Boston Itinerary

Do not leave Boston without a cup of clam chowder (or chowda as the locals call it). The Boston Harbor area offers so many great seafood restaurants, that you can’t go wrong with any that you select.

We chose to eat dinner at the legendary No Name Restaurant (I remembered eating there when I lived in Boston back in the 80s). But its history goes back even a few more decades than that.

The restaurant got its start in 1914 as a seafood stand on Boston’s South Pier without a name – and that name stuck. You can find it at 15½ Fish Pier East. Check out these other best places to eat in Boston.

As I mentioned earlier, we were staying at my friend’s house – who is a native Bostonian. She recommended Regina Pizzeria, which was established in 1926. It’s a small pizza place and had a long line, but even waiting in the rain was worth it.

There are two locations; we chose the original site in the North End at 11½ Thacher Street – not far off the Freedom Trail.

Go where everyone knows your name. The classic TV show, Cheers, got its inspiration from this Beacon Hill neighborhood bar, formerly called Bull & Finch Pub.

The original Cheers bar is located at 84 Beacon Street, with a replica located in Faneuil Hall.

Speaking of Faneuil Hall, this area offers many other dining options for your entire family. Check out Mike’s Pastry vs Modern Pastry, this can be helpful for choosing where you want to get your sweets!

Now that you’ve got options for your 2 days in Boston itinerary, relax and enjoy!

What are you going to do in Boston? We’d love to hear from you.

Other Massachusetts Guides

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