Long Weekend in Boston - A Perfect Boston 3 Day Itinerary

11 min read
A view of a city skyline with a body of water and green trees in front of it
Boston is one of the most-loved destinations on the East Coast of the US

Boston is one of the most well-known places in the United States. Located on the East Coast, the city is one of the US' oldest and is packed with fun attractions and historical landmarks.

If you've been considering checking out this New England destination, spending a long weekend in Boston is highly recommended. As the city is conveniently near Logan International Airport, you can easily fly in from almost anywhere in the states.

Thinking of adding Boston to your list of places to visit? Then keep reading for an attraction-filled Boston 3 day itinerary!

  • 3 day itinerary
  • Average of 6 stops per day

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3 Day Boston Itinerary

Boston Map

A map of Boston. Use the map to explore all the days and stops.

Marine Life Encounters and Historical Sites

A harbor with small boats on the water and a city skyline on the shore
You can go out on beautiful Boston Harbor on your first day in the city!

The first day of your Boston weekend trip will start on the water with a whale watching tour. Next, you’ll head to a Massachusetts landmark, the Boston Tea Party Ships and Museum, to learn about the event that led to the Revolutionary War.

At your next stop, the Faneuil Hall Marketplace, you can grab some delicious snacks and explore a range of independent shops. In the afternoon, you get to visit the New England Aquarium before going on a fun Freedom Trail pub crawl!

A whale's tail sticking out of blue harbor water
You can spot whales in Boston Harbor between April and October

Whale Watching Tour

A memorable activity that you may not expect to be offered in Boston is whale watching. Between April and October, whales migrate to the waters of New England and are often spotted in Boston Harbor.

On a whale watching tour, species to see include blue whales, humpback whales, and sei whales, among others. If interested in spotting these amazing creatures, you can find many whale cruise operators in the city.

A highly recommended operator to try is Boston Harbor Cruises who have teamed up with the Boston Aquarium for their Whale Watch Cruise. Once on the water, you’ll embark on an approximately four-hour journey with whale sightings guaranteed. Porpoise and dolphin sightings are likely too.

A red building with an old-fashioned ship to the side and a harbor in front of it
The Boston Tea Party Ships and Museum is an interesting historical attraction

Boston Tea Party Ships and Museum

A must-see attraction on your Boston travel itinerary is the Boston Tea Party Ships and Museum. As the name suggests, the museum is related to the historic Boston Tea Party, which involved early American settlers destroying tea supplies transported to the US from England in an act of rebellion.

At this fascinating museum, you can explore various exhibits covering this historical act and its effects on the creation of the United States we know today. You can also view replicas of the ships involved in the Boston Tea Party event.

While at the museum, you can even see historical re-enactments to liven up your experience. If interested in early US history, a visit to the Boston Tea Party Ships and Museum can’t be missed!

A red brick building with a square and statue in front of it
Faneuil Hall Marketplace features many unique shops and eateries

Faneuil Hall Marketplace

Faneuil Hall Marketplace is an iconic Boston attraction that today houses a lively market. At the marketplace, you can wander around an array of stalls. Items on offer range from souvenirs to home decor products and produce.

Having explored the stalls and kiosks, you can also find small independent stores to shop at. Everything from clothes and accessories to pet products and specialty gifts are for sale.

Before you leave, make sure you stop for a snack or meal at one of numerous cafes and restaurants. An array of dining options are available to choose from, including oyster bars, Japanese restaurants, and classic pretzel carts.

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The New England Aquarium is a fun place to visit during a long weekend in Boston
A fun place to visit during a long weekend in Boston is the New England Aquarium

New England Aquarium

If you’re going on a weekend trip to Boston with kids, visiting the New England Aquarium is a great way to keep everyone amused. Even if you aren’t traveling with children, going to the aquarium is a fun and laid-back activity to enjoy.

This vast aquarium houses a variety of sea creatures, from brightly colored tropical fish to sharks, penguins, and sea lions. The aquarium hosts lots of interactive experiences too. These events include seeing penguins up close and watching feeding sessions.

Additionally, you can head to a state-of-the-art IMAX theatre to watch marine life films. Movies on show include those on the life of sharks and the sea creatures of the Pacific Ocean.

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An obelisk monument with a statue of a man on the grass in front of it
The Bunker Hill Monument is one of many landmarks on the Boston Freedom Trail

Freedom Trail Tour

The Freedom Trail is a 2.5-mile route in Boston that passes numerous historical landmarks. You can find many Freedom Trail Tours, including self-guided tours, daytime tours, and private tours.

If you’re looking for something to do in the evening, then a pub crawl Freedom Trail tour is a must-try! During this unique experience, your guide will take you along the Freedom Trail, offering information on each sight you see.

Landmarks to spot on the route include the Old State House, the Granary Burying Ground, and the Bunker Hill Monument. Along the route, you also get to grab drinks at a range of renowned Boston.

Boston's Sports and Cultural Attractions

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A lake with green trees surrounding it and city skyscrapers in the background
The stunning Boston Public Gardens are one of many exciting stops on your second day

The second day of your three-day Boston itinerary begins at an iconic Boston sports venue, Fenway Park. After taking an informative tour of the renowned baseball stadium, you’ll next visit the Isabella Stewart Gardner Museum. At the museum, you can view an array of stunning artworks.

The art theme will continue at your next stop, the Museum of Fine Arts. The afternoon will be spent at two famous libraries: the Mary Baker Eddy Library and the Boston Public Library. Your day will end with a stroll around the scenic Boston Commons and Boston Public Gardens.

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A baseball field with a "Fenway Park" sign
A tour of renowned Fenway Park is a must for sports lovers!

Fenway Park Tour

One of the most well-known Boston Landmarks is Fenway Park, which is the home of the Red Sox Major League Baseball team. The perfect way to see this iconic sports venue is on a Fenway Park Tour.

On the tour of “America’s Most Beloved Ballpark,” you get the chance to go out on the field, explore the dugout, see the Red Sox Hall of Fame, and much more. Of course, you'll also learn a lot about the Red Sox organization and some of the team’s most famous players, past and present.

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A garden courtyard with greenery, a statue, and a building wall behind it
The Isabella Stewart Gardner Museum houses renowned artworks and a beautiful garden

Isabella Stewart Gardner Museum

Art enthusiasts will be very excited to make a trip to the Isabella Stewart Gardner Museum. Even if you're not the biggest art lover, viewing the incredible works on display is sure to please almost every traveler.

The museum is additionally notable as it's the site of one of the world’s most renowned art heists. In 1990, 13 priceless artworks were stolen. To this day, the pieces haven’t been recovered, nor the crime solved.

When visiting, pieces on display to admire include those by Rembrandt, Manet, Michelangelo, and many other world-famous artists. Be sure to also visit the museum garden, which features pretty floral displays and breathtaking sculptures.

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A place you must see on your Boston 3 day itinerary is the Museum of Fine Arts
A must-see attraction on your Boston 3 day itinerary is the Museum of Fine Arts

Museum of Fine Arts

Boston’s Museum of Fine Arts is known as one of the largest art museums in the world. This attraction houses approximately 450,000 artworks, including over 8,000 paintings. Artists with pieces on display include Vincent van Gogh, Claude Monet, and Auguste Renoir.

The types of exhibits to discover cover a broad spectrum of art styles. Displays range from those featuring modern art styles like street murals and tattoos to the art of ancient Greece and Egypt.

Exhibits include permanent and temporary ones, so you can see new works even if you’ve visited before. If looking for an exciting cultural activity, a visit to the Museum of Fine Arts is one of the things to do in Boston that has to be on your activity list!

Mary Baker Eddy Library and Mapparium

Mary Baker Eddy is a significant figure in the history of New England. The goal of the Mary Baker Eddy Library is to offer the public access to information on Mary’s life, achievements, and the church she founded in the 19th century.

There’s the Mapparium to discover too, which features a large glass spherical ceiling with a map of the world. When visiting the library, you can additionally appreciate the stunning 11-story neoclassical building it sits in.

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A stone library building with other buildings surrounding it and grass in front
One of the most stunning buildings in Boston is the Boston Public Library

Boston Public Library

Another must-see landmark to add to your three days in Boston itinerary is the Boston Public Library. This iconic library opened in 1852 and was notably one of the first free municipal libraries in the US.

The library houses over 24 million items, and you can view many of them when visiting. As you explore the library, you'll discover numerous genres of books, from fiction to nonfiction and classics to modern publications.

Various interesting and educational events for adults, teens, and kids are held at the library too. Be sure to check the Boston Public Library events calendar to see what’s on during your visit!

A statue of a man on a horse with a path and green garden surrounding it
Boston Common and Boston Public Gardens are a beautiful green oasis in the city

Boston Common and Boston Public Gardens

Boston Common and the adjoining Boston Gardens are some of the oldest public places in the United States. The Common is additionally named the oldest city park in the US.

The scenic Public Gardens and Common feature quaint lakes to walk around, beautiful flower gardens, and lots of greenery and open spaces. An iconic statue of George Washington sits within the park too.

Exploring these areas gives the feeling of being miles away from the bustle of the city! Wandering around the illuminated Boston Gardens and Common after dark is also one of the best things to do in Boston at night.

The Landmarks of the Boston Freedom Trail

A statue of a man on a horse with a white church steeple and trees in the background
You'll see an array of historical landmarks on your last day in Boston

Day three in Boston offers a more in-depth look at some of the famous landmarks on the Freedom Trail. Your day will start with a visit to the Old South Meeting House before moving onto the Old State House.

The modern-day Massachusetts State House is your next stop, and while there you can appreciate the building’s architecture and take a guided tour. You then get the chance to learn about African American history in Boston on the Black Heritage Trail tour.

Your three perfect days in Boston will end with a trip to two other historical Boston landmarks, the Old North Church and the Paul Revere House.

A tower with a pointed top and other buildings surrounding it
One of Boston's oldest landmarks is the Old South Meeting House

Old South Meeting House

Constructed in 1729, the Old South Meeting House is a historic Congregational church in downtown Boston. This landmark is especially well-known as the place colonists met to plan the Boston Tea Party. At the time of construction, the building was also the largest in the city of Boston.

Today, the Old South Meeting House is a museum that hosts various exhibits on the colonial United States, the Boston Tea Party, and more. Having viewed all the exhibits, be sure to also go to the gift shop to grab some fun souvenirs!

A red brick building with a white tower and other tall buildings surrounding it
The Old State House has an important place in American history

Old State House

Another must-see historic landmark in Boston is the Old State House. Built in 1713, the Old State House is one of Boston’s oldest buildings, and it’s also an important American Revolutionary War site.

In 1770, five colonists were killed by British Redcoats outside the building. This act was one of the events that led to the Revolutionary War. When visiting the Old State House today, you can see many exhibits in what is known as one of the best Revolutionary War museums in the US.

A red brick and white building with a gold dome roof and a US flag out the front
The Massachusetts State House is the current seat of government for the state

Massachusetts State House

One more of the various important sites to see on your Boston three day itinerary is the Massachusetts State House. The State House is the current State Capitol and seat of government for Commonwealth Massachusetts.

During your visit, you can appreciate the building's stunning architecture. You can also benefit from guided tours of the building where you’ll learn about its history and uses today.

A unique way to see the State House is on a Boston Food and Freedom Trail tour. This experience will take you to iconic sites on the Freedom Trail, including the Massachusetts State House, as well as to some outstanding Boston eateries. It’s the ideal tour for groups with both history enthusiasts and food lovers!

Black Heritage Trail

The Boston Black Heritage Trail is a fascinating route that takes you to various sites related to 19th century African American history. Interesting places to visit on the 1.5-mile-long route include the African Meeting House and the Abiel Smith School.

During your tour, you’ll learn about the life of African Americans in Boston in the 18th, 19th, and 20th centuries. You can also hear about various notable figures that helped end slavery and begin the Civil Rights Movement.

You can also stop at the interesting Museum of African American History. All tours along the trail are free thanks to the National Parks Service.

A water fountain with a red brick church with a white steeple behind it
Going to Old North Church is a must when exploring Boston

Old North Church

The Old North Church is another Boston landmark linked to the Revolutionary War. The building is where the “one if by land, two if by sea” secret code is said to be sent from. The Old North Church is additionally another of Boston’s oldest buildings, having been constructed in 1723.

When at the landmark, you can appreciate the charming church and learn about its history. The church also still hosts mass and other religious services. If interested in joining, check the church’s website for service times.

An old-fashioned dark wood house with a sidewalk and road in front of it
Paul Revere was a significant figure in the Revolutionary War

Paul Revere House

When visiting historical sites in Boston, a trip to the Paul Revere House is an absolute must. Paul Revere was one of the primary figures responsible for the Revolutionary War and American Independence.

The home was constructed in 1681, making it Boston’s second-oldest building. While at Paul Revere House, you can learn all about the life of the American Patriot and his contributions to the Revolutionary War.

You may also get to see some exciting events, such as historical re-enactments. Although you can head to the house alone, seeing it as part of a Revolutionary Story tour is highly recommended.

In Summary

Going to Boston for the weekend is always a good idea! If you’re visiting Boston for the first time, following this comprehensive travel itinerary will ensure that you see all the best landmarks and attractions in the city.

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Written by Alli Sewell

allisewell WRITER Currently based in Canada, I've also lived and worked in the UK and Brazil and travelled in North and South America, Europe, Australia, and Asia. I love finding the best photo-ops and food and drink locations wherever I go!


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