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Boston, MA: 3 Day Travel Itinerary

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Old South Church | Freedom Trail | Boston Massachusetts
Old South Church

In Boston, Massachusetts the juxtaposition of old against new is stark, bold, and beautiful. Skyscrapers soar next to 350-year-old churches. Brownstones and cobblestones are lovingly preserved while neighborhoods are in a constant state of reinvention.

The descendants of rabble rousing abolitionists, Bostonians remains an outspoken people. Whether blue-blood or blue-collar, locals consider it a birth right to speak their mind. Residents are passionate about their sports, food, and politics.

Beacon Hill | Boston, Massachusetts
Beacon Hill | Boston, Massachusetts

The Massachusetts state capitol has diversified since colonial times. Today, Boston is the largest city in New England and home to world-class healthcare, hi-tech, educational, and financial institutions. It is also a melting pot of ethnicities and cultures.

Our 3-day itinerary of things to do in Boston is a balance of must-see historical sights, museums, shopping, eating, and drinking. We think it is the perfect way to get to know the audacious and endearing seaport of Boston, Massachusetts.

Democratic Donkey Statue at the Massachusetts State House
Democratic Donkey Statue

For information on other Boston Travel locations read our articles on:

King's Chapel Burying Ground | Freedom Trail Boston
King's Chapel Burying Ground

Boston Travel Tips

Lodging: Book a hotel in the Historic Downtown area near Faneuil Hall, or by Copley Square. These locations will make it possible for you to park the car and walk to most locations. Make sure that your hotel has a parking garage or that there is safe, affordable parking nearby.

Transportation: Boston is notoriously difficult to drive in (trust me!). Plan to park your car and walk, or take the “T” (subway). Click here for schedules and maps.

Weather/Clothing: Boston has 4-seasons. Dress in layers; the weather is variable. Style is city-chic. Pretty much anything goes, but dress conservatively if you plan to visit churches.

Greenway Carousel | Waterfront | Boston, Massachusetts
Greenway Carousel | Waterfront

Day 1:

After settling in at your hotel, make your way to Boston Common. Pick up a map of the 2.5-mile Freedom Trail at the Visitor Center. The Freedom Trail is a walking route consisting of 16 stops at historic buildings, parks, and burying grounds. Each stop adds to the story of the American Revolution.

Boston Common | Boston Massachusetts
Boston Common

The self-guided Freedom Trail tour is great introduction to the city. Today, we will complete the first 11-stops (you will complete the last 5 stops on Day 3). See our post Boston Walk: Guide to the Freedom Trail for more information about each stop.

Sam Adams Headstone, Granary Burying Ground, Freedom Trail Boston
Sam Adams Headstone, Granary Burying Ground

Faneuil Hall is about mid-way along the route. As you approach the Sam Adams Statue, look down Congress Street for the light green columns of the New England Holocaust Memorial. Cross the street, and head to the memorial. Dedicated to the 6-million Jews who were killed by Nazi Germany in World War II, its 6 towers symbolize remembrance and hope.

New England Holocaust Memorial | Boston, Massachusetts
New England Holocaust Memorial

Next, retrace your steps to the Faneuil Hall Marketplace. The pedestrian-only complex consists of historic Faneuil Hall and the Quincy, North, and South Market buildings. See our post on Boston’s Faneuil Hall Marketplace for more detailed information.

Quincy Market at Faneuil Hall Marketplace | Boston Massachusetts
Quincy Market at Faneuil Hall Marketplace

Plan to stop here to eat and shop. The wooden carts and kiosks of Quincy Market are a great place to stock up on locally made crafts and sports paraphernalia. Quincy Market also houses the famed Food Colonnade with stall after stall offering regional and international favorite cuisines.

North and South Markets house retail stores selling crafts, apparel, housewares, and specialty items. There are also a number of sit-down restaurants and pubs on the grounds.

South Market | Faneuil Hall Marketplace | Boston, Massachusetts
South Market | Faneuil Hall Marketplace

When you reach the end of the marketplace, cross South Market Street and you will be on a section of the Rose Kennedy Greenway. To your right you will see the Greenway Carousel with its seats in the shape of animals native to Massachusetts. Beyond the carousel, is the Christopher Columbus Waterfront Park.

Union Oyster House | Boston, Massachusetts
Union Oyster House

After dinner at one of Faneuil Hall’s eateries, take North Street to Union Street. This will be a very short walk (Union Street is opposite the Holocaust Memorial). Stop in the Union Oyster House for dessert or an after dinner drink. The historic tavern has been serving New England favorites since 1826, and is one of the oldest continuously operating eateries in the United States (plus it has a cool sign).

Spend the evening exploring the historic pubs of this neighborhood including the the Green Dragon Tavern, the Bell in Hand Tavern, and many others.

Bell in Hand Tavern | Union Street | Boston, Massachusetts
Bell in Hand Tavern | Union Street

Day 2:

Spend the morning at one of Boston’s fine museums. We suggest either the Museum of Science, the Museum of Art, or the Isabelle Stuart Gardner Museum (our favorite!).

In the afternoon, visit Copley Square. This public green has much to explore. Around the perimeter of the square is the famous Fairmont Copley Plaza Hotel (check out the lobby), 200 Claremont Street (the glass skyscraper formerly known as the John Hancock Tower), the Boston Public Library, the Old South Church, and the Trinity Church.

Trinity Church | Copley Square | Boston, Massachusetts
Trinity Church | Copley Square

The Boston Public Library is a fascinating building, and free to tour. Check out the lobby, main staircase, Bates Hall, the Abbey Room, and interior courtyard. If the Old South Church and Trinity Church are open to the public, they are worth a close look.

Interior Courtyard | Boston Public Library
Interior Courtyard | Boston Public Library

When you are done exploring Copley Square, spend some time at the posh Copley Place and Prudential Tower shopping malls. The malls are linked by a glass bridge that spans Huntington Avenue.

Prudential Center | Boston, Massachusetts
Prudential Center

Exit the Prudential Center by its parking garage, and walk one block over to Newbury Street. Meander along this famous Boston shopping street to window shop Chanel, Cartier, and Burberry. The lovely Emmanuel Episcopal Church is also on Newbury.

Tonight, take in a show or concert. Buy tickets in advance at StubHub.

Shopping Newbury Street, Boston Massachusetts
Newbury Street

Day 3:

In the morning, try a Boston Duck Boat Tour. On the roughly 80-minute sightseeing excursion you will ride around in one of the whacky, colorful amphibious vehicles you are sure to have seen around town. The tour will take you past Boston sights by land and water. As an alternate activity, visit the New England Aquarium or take a whale watch.

Boston Duck Tour | Boston, Massachusetts
Boston Duck Tour

In the afternoon, finish the last 5-stops of the Freedom Trail and explore Boston’s North End (famous for its great Italian food).

Haymarket Boston | Historic Outdoor Market
Haymarket Boston | Historic Outdoor Market

Begin your exploration at the Boston Public Market. The Public Market is year-round indoor marketplace selling locally produced New England products. If it is a weekend, also check out the nearby Haymarket Square fruit and vegetable outdoor market.

Prado Mall | North End | Boston, Massachusetts
Prado Mall | North End

From the Public Market, do an in-depth neighborhood walk of Boston’s North End. The North End is known for its historic landmarks and Italian influences. See our article Boston Walk: Things To Do in Boston’s North End for a detailed walking route.

This evening enjoy dinner at one of the many fine restaurants on Boston’s waterfront or in Chinatown.

Waterfront | Boston, Massachusetts
Waterfront | Boston, Massachusetts

It’s such a great walking city, we know your going to love it, Laura and Randy

For information on other Boston Travel locations read our articles on:


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