The Perfect 2, 3 or 4 Days in Boston Itinerary

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by Audrey Webster


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As one of the oldest cities in the country, Boston is filled with history. It’s a mash-up of cobblestoned streets and historic buildings with modern skyscrapers. There are a few places you cannot miss during a 2, 3, or 4 days in Boston itinerary, as well as some lesser-known parts of the city we’ll cover here.

As one of the most dynamic and historic cities in the country, there is a lot to do in Boston and so much that you can’t miss. From American history to esteemed universities to excellent museums and fantastic food (there’s more than clam chowder!), Boston has something to offer everyone.

How Many Days in Boston?

When in the initial stages of planning a trip, many do wonder how many days to spend in Boston in order to do this New England city justice.

With 2 days in Boston, you’re just scratching the surface. Most of the city’s main attractions are clustered together, so you could see a lot in 2 days, but you’re also missing out on some cool parts that make the city unique.

If you have 3 days in Boston, you’re in good shape to see all the highlights as well as some lesser-known sites. You’ll be able to strike a balance between visiting historic landmarks and more trendy neighborhoods.

If you’re lucky enough to have 4 days, you can see more of the city at your leisure or use the fourth day to take a day trip to somewhere nearby. There is no shortage of historic sites and beautiful nature just outside Boston. 

Boston Skyline
Boston Skyline

Getting To & Around Boston 

You’re most likely arriving in Boston through the Logan International Airport. You can easily hail a cab, take the GO Boston Shuttle, pre-book a transfer or use public transportation to reach downtown.

If you’re visiting from another city or town in New England or even some city further south such as Washington DC or New York, you might arrive on a train or bus. Make sure to find out which train or bus transfers you need to make depending on where you’re coming from. You can view schedules here.

The Massachusetts capital is a very walkable city and it’s not actually that big. In fact, one of the best things to do in Boston is walk the Freedom Trail. Many of the most historic landmarks are located near each other.

Boston is also well-connected via a subway system, known locally as the T. You can easily get around the city using this if you want to reach somewhere a bit further afield.

Alternatively, there is the Hop On/Hop Off Trolley Tour that provides a convenient way to see the city. Taxis and rideshare are both readily available as well. It is also included in the Boston Go City Pass, which will also save you on entrance fees to many of the paid attractions listed here.

Boston Tea Party Ships & Museum
Boston Tea Party Ships & Museum

2, 3 or 4-Day Boston Itinerary

If you’re spending a few days in the Massachusetts capital, then there are a number of guided tours that you can take to get an overview of the city such as this historical walking tour, this bike tour or this food tour.

Day 1 – Freedom Trail, Museums, Quincy Market & More

Walk the Freedom Trail

This 2.5-mile trail covers many of the historical highlights in Boston. You’ll want to dedicate a few solid hours to walking the trail. You can opt to walk the entire thing or a portion of it.

There are also guided tours available such as this 2-hour walking tour, which could be helpful for providing context to the landmarks as you pass them. Here are the landmarks you can expect to see:

  • Boston Common & Boston Public Garden
  • Massachusetts State House
  • Park Street Church
  • Granary Burying Grounds
  • Boston Latin School/Benjamin Franklin Statue
  • Old South Meeting House
  • Old State House
  • Faneuil Hall
  • Site of the Boston Massacre
  • Paul Revere House
  • Old North Church
  • USS Constitution
  • Bunker Hill Monument

You could spend however long you’d like walking the Freedom Trail and note that it doesn’t cost anything to walk the trail, but there are generally entrance fees for the various sites.

Depending on how long you want to spend, take the time to walk by these places and pick one or two that interest you to plan to visit those places. With that in mind, plan to spend 2-3 hours on the Freedom Trail.

Old State House on the Freedom Trail
Old State House on the Freedom Trail

Boston Tea Party & Ships Museum

Veer off Freedom Trail just slightly to pay a visit to the Boston Tea Party and Ships Museum.

The museum is chock-full with historical experts, interactive exhibits, full-scale replica sailing vessels, and historic artefacts to make this monumental event in America’s history come to life. You can pre-book tickets here.

If you have some time to spare, you can watch an award-winning documentary in Minutemen Theatre that depicts the events that led up to the American Revolution. 

Next to the museum, don’t miss the Observation Deck at Independence Wharf, either, where you can get excellent views of the harbor.

Quincy Market

Quincy Market is where old and new seamlessly merge. Here you can find hundreds of shops, both inside and outside the building. The market was established in 1825 and spans three buildings: Quincy Market, South Market, and North Market.

It’s another great place to stop as you’re walking the Freedom Trail to grab a bite to eat or do some souvenir shopping. The market is especially charming during the winter months when it’s decorated for the holidays. Quincy Market was named a National Historic Landmark in 1966. 

Quincy Market
Quincy Market

Go to a Red Sox game

Go see the “Green Monster” for yourself during your visit to Boston. Even those who wouldn’t consider themselves baseball fans will enjoy seeing a game at Fenway Park.

It’s been the home of the Boston Red Sox since 1912, making it the oldest stadium in Major League Baseball. If you don’t have time to see a game, you can still take a guided tour of Fenway. It’s a great way to wrap up your first day of sightseeing in Boston. 

If it’s not the season for baseball or you don’t care to go to a game, then use this time to stroll along the Charles River Esplanade or, perhaps, visit the nearby Boston Museum of Fine Arts. You could also simply relax in the tranquil surroundings of Back Bay Fens Park.

Day 2 – Boston’s Museums

John F. Kennedy Presidential Museum & Library 

This exceptional museum is dedicated to the life and accomplishments of U.S. President John F. Kennedy.

Here, you’ll wander the permanent exhibit that uses large-screen projections, interactive displays, original artefacts, and re-mastered films to learn more about the former president’s life. Consider reserving tickets online in advance to save you time at the door. You can also opt for a guided tour.

A visit to the JFK Presidential Museum & Library is a great way to kick off your second day. 

Inside the JFK Presidential Library
Inside the JFK Presidential Library

Institute of Contemporary Art

If you have 2 days, you should consider visiting one of the many local museums. A city that’s so full of history has some great historical museums, but it also has notable art museums like the Institute of Contemporary Art.

Here you’ll find both permanent and rotating exhibits featuring contemporary artists and their work. The museum is located in a beautiful building on the waterfront overlooking Boston Harbor, so you can also take in the view. It’s recommended that you book tickets in advance. 

Isabella Stewart Gardner Museum

This museum is known for its beautiful architecture and courtyard garden. It’s a great museum to visit if you want one that is a little less crowded than other larger museums in the city. Beginning in the late 1800s, Isabella started collecting rare books, manuscripts, and pieces of art to fill her home.

Over the course of her worldwide travels, she acquired art like Rembrandt’s Self Portrait and Titian’s Europa. The museum as it stands today was built in 1901. She lived on the fourth floor and spent the remainder of her life arranging the art throughout its halls.

It’s a unique museum that’s a quiet way to spend the afternoon. If this or any of the other museums don’t interest you, there are plenty of other museums in Boston to take in. For instance, the Museum of Science – located in a building overlooking the Charles River, is an excellent place to visit if you happen to be traveling with children.

Day 3 – Boston Common, Trinity Church, Paul Revere House & More

Boston Common

You might’ve already passed through Boston Common if you walked the entirety of the Freedom Trail. If you didn’t stop for long then, it’s worth your time to dedicate a couple hours to really enjoying the park. Boston Common is America’s oldest public park having been established in 1634 and is located in the Beacon Hill neighbourhood of Boston.

Today, the park is filled with fountains, picnic tables, and green spaces for visitors to lounge and enjoy the day. Make sure to stroll through the adjacent Public Garden, as well, to truly enjoy this urban green space. If you’re seeing Boston in 3 days, then a visit to Boston Common is a great idea.

Boston Common
Boston Common

Trinity Church

When you start exploring Boston, you’ll immediately notice Trinity Church in Copley Square. This historic stone church sits squarely in the middle of downtown’s towering skyscrapers. It’s considered by the American Association of Architects as one of the top 10 buildings in the country.

The parish located there today was founded in 1733, which is more than 150 years before the church was built in 1877. You can enter Trinity Church on your own or schedule a tour with a knowledgeable tour guide to learn more about the church’s history. 

It looks striking as it’s sandwiched between modern skyscrapers like the John Hancock Tower and the Prudential Tower and really symbolises Boston’s mingling of old and new.

Paul Revere House

Located in the North End neighborhood, the Paul Revere House was the former home of the famous Founding Father Paul Revere. He played a pivotal role in the American Revolution, noted in history books for his famous “midnight ride” to warn colonists that the British were approaching Boston.

The home was built in 1680 and is downtown Boston’s oldest building. Inside, the home is set up to mimic what it would have looked like while Revere lived there. In fact, 90% of the structure today is original material, including doors, windows, flooring, and internal wall material.

You can pop into this Boston museum for a self-guided tour or try to time your visit to see colonial reenactors demonstrate key moments of America’s history. 

If this doesn’t interest you as much or if you’re traveling with children, consider, as well, heading to the nearby New England Aquarium where you can learn all about local marine life or you can take a food tour of North End.

Paul Revere House
Paul Revere House

The Museum of Bad Art

You’ve probably never been to a museum that focuses on bad art. The Museum of Bad Art houses “art too bad to be ignored” and is a highlight worth adding to your time in Boston. It’s the world’s only museum dedicated to bad art that began in the basement of a private home.

The museum has since grown into a local favorite that shines the spotlight on quality bad art. It’s a quirky and fun addition to your Boston trip, especially if you happen to be planning a 3-day itinerary. 

Day 4 – Lexington & Concord, Salem or Cape Cod Day Trip

Lexington and Concord

Lexington and Concord is arguably the most famous site of the Revolutionary War. For history buffs, this is a great way to round out your 4 days in Boston. It’s where the first shots of the war were fired.

To reach Lexington, you’ll take the subway and bus for a total travel time of about 45 minutes before getting off at Lexington Battle Green. You can reach Concord by taking the MBTA directly from Boston.

Lexington Green is a good starting point for your visit. This small town is home to the Belfry that sounded the alarm in 1775 to call the militia to fight. Here, you’ll also find John Hancock’s childhood home or Buckman’s Tavern. In Concord, make sure you visit the Old North Bridge.

You can also find Walden Pond, made famous by writer Henry Thoreau, and Louisa May Alcott’s “Orchard House”. There’s a lot to see during a day trip to Lexington and Concord, so make sure you leave early in the day to give yourself ample time. 

Old North Bridge in Concord
Old North Bridge in Concord

Salem

You’ve most likely heard of Salem, Massachusetts due to its famous 1692 witch trials. Salem is only about 30 minutes from Boston, so it’s an easy day trip. You can easily reach it by taking the commuter train that connects the cities, a high-speed ferry or an organised day tour.

During your day in Salem, make sure to visit the Salem Witch Trials Memorial, Peabody Essex Museum, the Old Town Hall, and the Witch House. You can end your day with a visit to Winter Island Park and Lighthouse.

As you might’ve guessed, one of the best times of year to visit Salem is Halloween. The little town comes to life with spooky decorations.

Cape Cod

Without a doubt, Cape Cod is beautiful, especially in summer. This stretch of coastline is full of charming towns, great seafood, and relaxing beaches.

Cape Cod is about 3 hours from Boston by car, which tends to be a little long for a day trip. Instead, you can take the Cape Cod Fast Ferry from Boston to Provincetown, which is the largest town on the Cape.

In Provincetown, you can enjoy the local art galleries, lounge on the beach, and walk around and enjoy the quaint homes and shops.

If you have more than 4 days in your Boston itinerary, spending more than one day on the Cape is a relaxing way to bring your time in the area to a close.

Cape Cod
Cape Cod

Where to Stay in Boston

Harborside Inn – This 3-star hotel in downtown Boston is a great choice for mid-range travelers to the Massachusetts capital. There are a number of great rooms to choose from, a wonderful location for exploring the city and plenty of other amenities to enjoy.

Omni Boston Hotel – If you’re looking for luxury while in Boston, then this sophisticated hotel is a great option. They have a range of lovely rooms on offer and an unbeatable location for exploring all this historic city has to offer.

HI Boston – Those visiting Boston on a budget will love this backpacker’s hostel in the center of the city. They have a range of both dorms and private rooms on offer along with other perks and great common areas for guests to enjoy.

Not quite what you’re looking for? Click here to browse more Boston hotels!

The perfect itinerary for Boston is the one that’s packed with what excites you most. If you’re a history buff, you’re going to love it here. Foodies, explorers, and everyone in between will find something to love in Boston.

Are you planning a trip to Boston? Have any questions about this itinerary? Let us know in the comments!

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Audrey Webster is a writer for The World Was Here First. She is an Oregon native who has visited countries across the globe and currently spends her weekends exploring the Pacific Northwest and surrounding states. Her approach to traveling combines exploring famous tourist sites and wandering off the beaten path to discover new destinations.

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