Long Weekend in Boston - A Perfect Boston 3 Day Itinerary
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Boston is one of the most well-known places in the United States. Located on the East Coast, it is one of the oldest cities in the US 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!
Planning a last-minute trip to Boston?
When visiting Boston, book your accommodations and experiences before you go. We've pulled together top suggestions below.
🏨 Top accommodations in Boston
- The Eliot Hotel (rated highly)
- InterContinental Boston (5-star rating)
- The Colonnade Hotel (relax by the pool)
☂️ Top tours and experiences in Boston
3 Day Boston Itinerary
Boston 3-Day Itinerary Video
Check out our highlights video of the stops covered in this Boston itinerary.
Boston 3-Day Itinerary Map
A map of Boston. Use the map to explore all the days and stops.
Marine Life Encounters and Historical Sites
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!
Whale Watching Tour
A memorable activity that you may not expect to be offered in Boston is whale watching. If you want to spot whales, the best time to plan a trip to Boston is between May and October. This time period is when whales migrate to the warming waters of New England and are often spotted in Boston Harbor.
Species to see on a Boston whale-watching tour include blue, humpback, and sei whales, among others, and Boston Harbor Cruises is a great tour operator to book with. The company has teamed up with the Boston Aquarium for its unique Whale Watch Cruise.
Once on the water, you'll embark on a four-hour journey with whale sightings guaranteed. Porpoise and dolphin sightings are also likely.
☂️ See Boston Harbor on a tour
- Sightseeing Day Sail Around Boston Harbor (likely to sell out)
- Boston Harbor Brunch Cruise
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!
🏨 Accommodations near Boston Tea Party Ships & Museum
- The Langham (5-star rating)
- Canopy by Hilton Boston Downtown (4-star rating)
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.
🏨 Accommodations in close proximity to Faneuil Hall
☂️ See Faneuil Hall on a tour
- Guided Walking Tour of the Freedom Trail (high demand)
- Boston's Official Freedom Trail Walk Into History Tour (very popular)
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.
🏨 Places to stay close to New England Aquarium
- Boston Marriott Long Wharf (rated 4-stars)
- Boston Harbor Hotel
☂️ See New England Aquarium on a tour
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.
🏨 Stay nearby Freedom Trail
Boston's Sports and Cultural Attractions
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.
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.
🏨 Stay nearby Fenway Park
- Hotel Commonwealth (top-rated)
- Residence Inn by Marriott Boston Back Bay Fenway (relax by the pool)
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.
☂️ Discover Isabella Stewart Gardner Museum on a tour
- Boston City View Bicycle Tour by Urban AdvenTours (rated five stars)
- Go City - Boston All-Inclusive Pass With 45 Attractions & Tours
🏨 Stay nearby Isabella Stewart Gardner Museum
- Sonder at Pierce Boston (rated 4-stars)
- The Revolution Hotel
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!
🏨 Accommodations near Museum of Fine Arts, Boston
- Oasis Guest House
- The Verb Hotel (well-regarded)
☂️ Visit Museum of Fine Arts, Boston with a tour
- go City All-Inclusive Pass With 40 Attractions (usually sells out)
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.
🏨 Accommodations near The Mary Baker Eddy Library
- Four Seasons Hotel One Dalton Street (5-star rating)
- Boston Marriott Copley Place (offers a pool)
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!
🏨 Accommodations nearby Boston Public Library - Central Library
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.
🏨 Accommodations in close proximity to Boston Common
- Hotel AKA Back Bay (4-star rating)
- The Liberty
☂️ Visit Boston Common on a tour
The Landmarks of the Boston Freedom Trail
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.
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!
☂️ Experience Old South Meeting House with a tour
- The Revolutionary Story in Depth Narrative Walking Tour of Boston (often fully booked)
- Boston Hop-On Hop-Off Trolley Tour With 14 Stops (widely sought after)
🏨 Accommodations in close proximity to Old South Meeting House
- The Eliot Hotel (rated highly)
- InterContinental Boston (5-star rating)
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.
☂️ Discover Old State House on a tour
- Freedom Trail - Small Group Tour of Revolutionary Boston (extremely popular)
- North End to Freedom Trail Food & History Tour (highly rated)
🏨 Nearest accommodations to Old State House
- Boston Yacht Haven (4-star rating)
- CitizenM Boston North Station
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!
🏨 Accommodations in close proximity to Massachusetts State House
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.
🏨 Stay near the Black Heritage Trail
- The Colonnade Hotel (relax by the pool)
- Seaport Hotel Boston (4-star rating)
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.
🏨 Accommodations near the Old North Church
- Homewood Suites by Hilton Boston Seaport District (chill out by the pool)
- Club Quarters Hotel Faneuil Hall
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.
🏨 Accommodations in close proximity to The Paul Revere House
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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