Summer in Boston: A Boston Bucket List Itinerary • Trimm Travels

It’s summer time and while there are an infinite amount of destinations, summer in Boston is a popular featured choice. Why? Besides its rich history, it’s a walkable city with many different landscapes, land and water activities, and photo opportunities. I truly loved visiting and now I’m sharing this Boston bucket list itinerary to help you plan the best summer Boston trip. Whether historical, iconic, both, or neither, these are the things you should see while visiting Boston in the summer!

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wooden sign with letters spelling out BOSTON in different colors against a night sky

Summer in Boston

aerial shot flying into Boston with the water, sand, boats, and downtown in the background against a blue sky

Green spaces, picnic blankets in the park, sailing, laying out by the water, Swan Boats…summer in Boston does have it all. Below, you will find a comprehensive (though not all-inclusive) list organized by neighborhood to help you create your perfect Boston bucket list itinerary!

Beacon Hill

Boston Public Garden

Established in 1837, the Boston Public Garden was the first public botanical garden in the United States. The parks and recreation department maintains the Victorian style of gorgeous, colorful flowers found throughout the walkways of its roughly 24 acres.

The most noticeable things to do in the Boston Public Garden are taking a ride on the Swan Boats, sitting on the bench Robin Williams made famous in Good Will Hunting, and seeing the Make Way for Ducklings bronze sculpture.

Boston Common

Founded centuries prior in 1634, Boston Common is America’s oldest park. Many historical events took place here in the Common from the Revolution to World War II to Martin Luther King, Jr rallies. Today, the Common is still used for freedom of speech and rights but also as a place to relax and gather with family and friends.

bronze statues of two frogs fishing at a pond's edge in the Boston Common

While in the Common, don’t miss the cute Boston Common Frog Pond and the Frog Pond Carousel!

Massachusetts State House

In my opinion, one of the prettiest buildings in all of Boston is the Massachusetts State House. The capitol building of the Commonwealth of Massachusetts has a beautiful golden dome and is the oldest building in the Beacon Hill neighborhood. Free tours are conducted on weekdays from 10:30 am to 3:00 pm and last around 45 minutes.

Acorn Street

If your address is on Acorn Street, you live on one of the most high-profile streets in all of Boston. The street is private and yet the homeowners continue to allow thousands of visitors annually to take photos. Dubbed the most photographed street in America, the old cobblestone street takes one back to Colonial times and even features a large American flag.

Longfellow Bridge

The Longfellow Bridge is a steel rib arch bridge over the Charles River connecting Boston’s Beacon Hill with Kendall Square in Cambridge. Started in 1900, completed in 1907, and rebuilt in 2018, the one-third mile long, 105-foot wide bridge has the fun nickname of “Salt and Pepper Bridge” because of the shape of its towers. It’s a unique pedestrian bridge that is pretty anytime but especially at sunset!

Cheers

You do wanna go where everybody knows your name, right? Whether or not you are a Cheers fan, don’t miss stopping for at least a snap of this Boston iconic restaurant. If you have time, take a look at the menu and grab a bite! Cheers!

You might also like: FUN RESTAURANTS IN BOSTON + WHAT TO ORDER

Back Bay

Boston Public Library

One of the prettiest public libraries in the United States, the Boston Public Library is worth seeing inside and out. The stunning architecture from Bates Hall with its famous green lamps…

Heather (me) from Trimm Travels standing on the grand staircase inside the Boston Public Library with sunlight beaming in

…to the Grand Staircase of the McKim Lobby leading to the second floor, this library definitely has unique photography opportunities.

inside the Map Room Tea Lounge with a tea cup in the foreground and lighted letters spelling out TEA and BAR in the background

Don’t forget to visit the Courtyard and even have afternoon tea in the Map Room Tea Lounge-Boston’s first tea-infused cocktail lounge!

Copley Square & Trinity Church

view of Copley Square with flowers in the foreground, green grass and picnics in the mid-ground, Trinity Church in the background against a blue sky

Trinity Church in Copley Square

Home to the Boston Public Library is the famous Copley Square. Renamed from Art Square as it was known prior to 1883, it is now named for the painter John Copley. As its name states, the Square is home to many beautiful, architectural landmarks.

One of these is Trinity Church, a National Historic Landmark recognized by members of the American Association of Architects as one of the top ten buildings in the entire country!

the Old South Church in the Copley Square area of Boston against a gray sky

Old South Church in Boston’s Copley Square

Other landmarks around Copley Square include the Boston Public Library, the Old South Church, and the John Hancock Tower.

Boston Marathon Finish Line

A half block from Copley Square is the Boston Marathon Finish Line. Having completed four half-marathons, it was definitely cool for me to see. However, even if you aren’t into marathons, it is still an iconic thing to see.

Mapparium at Mary Baker Eddy Library

inside of a 3-story globe of the world at the Mary Baker Eddy Library in Boston

Looking for uniqueness in Boston? Found it! Calling all travelers, geographers, and art enthusiasts…

The Mapparium at the Mary Baker Eddy Library is a stained glass globe (inside-out), standing three stories tall. The kicker? You can walk through it from one side to the other! It is illuminated by LED lights and is a rare chance to get an undistorted view of the Earth.

The globe is by far one of the most interesting attractions I have ever seen traveling!

Shop on Newbury Street

orange brownstone buildings on the famous Newbury Street in Boston's Back Bay area

Newbury Street in Boston’s Back Bay is a great place for shopping, dining, and nightlife. It’s also very picturesque and due to its high-end shops, it is one of the most expensive streets in the world.

My personal experiences on Newbury Street include perusing Trident Booksellers, purchasing dresses at Peruvian Connection, grabbing a Thai massage at Viyada Thai Spa, and dining at many of its fantastic restaurants. See my dining posts below for where to eat and what to order.

Back Bay East

Charles River Esplanade

The Charles River Esplanade is a 3-mile outdoor park stretching down the river’s south side (Boston side). It’s a gorgeous place to watch the sunset, sailboats, and kayakers. Have a picnic, take advantage of fitness classes, bike, stroll, or take the kids to the playgrounds. There are endless amounts of things to do!

Downtown Boston

Faneuil Hall Marketplace

exterior of Quincy Market with trees against a blue sky in Boston

Faneuil Hall Marketplace, nicknamed “The Cradle of Liberty” in 1742, is 360,000 square feet of office and retail space. Close to the waterfront, this bustling must-see marketplace also contains the Quincy Market Colonnade. Shop, eat all kinds of fantastic food from around the world, and walk the cobblestone promenades!

New England Holocaust Memorial

looking through the Holocaust Memorial in Boston-a glass structure with steel columns and aqua paneling

The New England Holocaust Memorial is open 24 hours and pays tribute to six million Jews killed as well as the survivors. Stephen Ross, himself a Holocaust survivor, founded the memorial which consists of 50-foot tall spires that are luminous and meant to be a “beacon of light to fight darkness”. It is something everyone should see but fair warning, it is an emotional experience.

Granary Burying Ground

Established in 1660, Granary Burying Ground was developed to help overcrowding in King’s Chapel Burying Ground. Although believed to have 5,000 interred, it only has around half that number of gravestones and tombs.

Among its most famous graves are those of Paul Revere, Samuel Adams, John Hancock, and Benjamin Franklin’s parents.

Boston Public Market

Definitely hit up Boston Public Market. No, not the restaurant. 😉 Open year-round, the indoor Market features around 30 local vendors who prepare meals, sell fresh produce, and offer handmade goods. Take a stroll around-it’s especially great for a rainy day!

Boston Tea Party Ships & Museum

Boston Party Tea Ship yellow replica and red museum building on a pier over the water against a blue sky

Go back in time to be part of the events that sparked the Revolution. Featuring two (of three) replicas, Brig Beaver and Eleanor, the museum reenacts the Boston Tea Party. A Son of Liberty will guide you through the events and explain how they protested against the British selling tea from China in America without paying taxes.

Learn how they threw all of the chests of tea into the Boston Harbor sparking rage from the British government. Seen as an act of treason, this escalated quickly into war.

Brattle Book Shop

many rolling carts of colorful books set outside in a brick walled alley

The cool thing about Brattle Book Shop is that part of it is outdoors. It’s one of the largest and oldest used bookstores in the country and even has a rare selection of antiquarian books. For bookworms and collectors alike, this bookstore is a unique stop in Boston.

Underground at Ink Block

colorful painted streaks on the road and street art on the the sides of freeway underpass and columns

If you like street art and accessing unique types of outdoor activities, Underground at Ink Block is the place for you. Technically located in South Boston, this cultural attraction stretches across 8-acres of an underpass. The murals are stunning and there is even a parking structure, bike storage, biking paths, fitness classes, food options, and a dog park!

The Rose Kennedy Greenway

The Greenway is a 1.5-mile park that winds through Boston. It has many sculptures, fountains, events, food trucks, as well as a carousel, and even beer and wine gardens. Plan a picnic with the family or an outing with friends and make it your own adventure!

The Boston Stone

closeup of the round orange Boston Stone built into the side of a red brick building

An interesting landmark that definitely flies under the radar is the Boston Stone. Very unassuming, it often goes unnoticed as people pass it on the street. It’s a flat stone built into the side of a building on Marshall street. The two-foot wide stone is inscribed with “Boston Stone 1737”. Just keep an eye out for it if you are doing the Freedom Trail as it is near there in the north downtown area.

King’s Chapel Burying Ground

Founded in 1630 at the time of Boston’s settlement makes King’s Chapel Burying Ground the oldest burial ground in the city. Part of The Freedom Trail, it gets its name from occupying the previous site of a church but is not actually affiliated with any church.

Most notables buried here include Mary Chilton (believed to be the first woman off the Mayflower), John Winthrop (the first governor of Massachusetts), and William Dawes who accompanied Paul Revere on his 1775 ride to Lexington.

Boston Massacre Site

The Boston Massacre Site is located downtown right behind the Old State House at the corner of State and Congress Streets. It marks the historical event where British soldiers killed five Bostonian civilians or colonists. The event has been called the Redcoats vs the Sons of Liberty and has gone through many name changes including the “bloody massacre”.

West End

Zakim Bunker Hill Memorial Bridge

the Zakim Bridge lit up purple at night over the Charles River with colorful light reflections in the water against a black, clear night sky

Boston has many bridges but my favorite is the Leonard P. Zakim Bunker Hill Memorial Bridge. Named for Civil Rights activist, Lenny Zakim, the bridge serves as the north entrance and exit for Boston. Completed in 2003, it is one of the widest cable-stayed bridges in the world. The bridge is beautiful during the day but its nighttime lights definitely give it personality!

On the north side of the bridge, check out North Point Park and Paul Revere Park. If you have more time to explore this area, be sure to see the Bunker Hill Monument. If you are completing the Freedom Trail, you will see this anyway as it is one of the Trail’s last stops.

TD Garden

While admiring the Zakim Bunker Hill Bridge, be sure to glance up at TD Garden. Boston’s version of NYC’s Madison Square Garden, it is New England’s largest sports and entertainment arena. Catch a concert, attend a Bruins or Celtics game, or even take a tour of The Sports Museum.

The Liberty Hotel

inside of the unique Liberty Hotel with its exposed brick multiple story atrium with a multi-colored carpet feature between double escalators

If time permits and you love unique views, stop into The Liberty Hotel to snap a few photos and grab a cocktail. The exposed brick, multiple-story open atrium and bar, wrought iron chandeliers, and unique carpet feature between the double escalators make quite the scene!

The hotel has an interesting history. To learn more, tours, offered on Wednesdays at 2:00 pm by reservation only, are 30 minutes long and include a glass of champagne!

North End

The Paul Revere House

exterior of Paul Revere's old house-now museum against a blue sky in Boston

A National Historic Landmark, The Paul Revere House was the home of the famous patriot during the American Revolution and his famous midnight ride. The house-turned-museum is a valuable place for education, colonial reenactments, and tours. Learn more about the man who is thought (but not proven) to have yelled, “The British are coming!”

Old North Church

Playing THE part in the warning of the British coming is the Old North Church. On the night of Paul Revere’s famous midnight ride in April 1775, two church members climbed to the steeple to shine two lanterns bright. This indicated the British were indeed coming by sea across The Charles River and not by land which would have been only one lantern. This event marked the start of the American Revolution.

All Saints Way

patriotic bows, flowers, plants, saints sculptures and other colorful trinkets and lights surrounded by red brick

Just saying…this is something you must lay eyes on. It is super fascinating. All Saints Way is the culmination of collections by now 63-year-old, Peter Baldassari. Now a tourist attraction, his collection of trinkets having all things to do with saints has become a giant roadside shrine!

Find it in Boston’s North End between 4 and 8 Battery Street. You can also see the map at the end of this post!

Skinny House

Also in Boston’s North End, travelers can find the Skinny House. Located at 44 Hull Street, the four-story house is 10.4-feet at its widest point and 6.2 feet at its narrowest. Declared as the narrowest house in Boston by the Boston Globe, it is believed to have been created as a “spite house” and is said to be “vertical living” at its best!

Around Boston

Fenway Park

The pride of Boston and the oldest ballpark in Major League Baseball, Fenway Park is on the National Register of Historic Places. Home of the Red Sox, the ballpark has kept its old-style charm while boasting the tallest wall in the MLB (the “Green Monster”) at 37 feet tall. It also features a rooftop garden, Fenway Franks, guided tours, and true nostalgia!

Harvard University

building with a colorful, patterned roof and gothic architecture on Harvard's campus surrounded by green trees against a blue sky

Founded in 1636, Harvard University is one of the most prestigious universities in the world. Located in Cambridge, Harvard was named for its first major benefactor, John Harvard. The private Ivy League research institution is the oldest of its kind in the United States and has a student body of around 35,000.

Massachusetts Institute of Technology

white sculpture piece on MIT's campus with green grass, trees and a cement building and blue sky

Also located in Cambridge but not an Ivy League university, the Massachusetts Institute of Technology is prestigious in its own right. Founded in 1861, MIT is just as competitive and distinguished as its “neighbor”; however, it is much smaller with a student body of approximately 12,000.

Some notable areas to see at MIT are the Great Dome, MIT Chapel, the exterior of Kresge Auditorium, and various public art installations such as Alchemist on the Stratton Student Lawn.

Where to Eat in Boston

Did you think I had forgotten food? NOPE. Boston is a fantastic foodie town! One can’t think about visiting Boston without eating their way through it. Take a look at these posts for cool restaurants, what food and drink to order, and even the best places for Boston cream pie!

a traditional lobster roll with a side of kettle potato chips and coleslaw with a lemon wedge garnish on a white plate

overhead view of a round Boston cream pie with chocolate and white chocolate swirls with a sliced strawberry garnish on a white plate on a dark green marble tabletop

Boston Transportation & Accommodations

orange kayaks dot the blue waters of the Charles River with the Boston city skyline in the background against a blue sky

There are so many choices for accommodations in Boston. Whatever your style may be, the option is available. For all of your transportation and accommodation needs, Rome2rio is a one-stop planning tool. They use their many resources and platforms to find the best prices on everything from airfare to hotels and car rentals. This is especially nice if Boston is just one stop on either a multi-city tour within the United States or part of an international trip!

MAP IT!

PIN IT!

Pinterest graphic with four colorful photos of Boston and the title "Summer in Boston: A Bucket List Itinerary"

Pinterest graphic with two colorful photos of Boston and the title "Summer in Boston: A Bucket List Itinerary"

a lone red sailboat in the Charles River at golden hour with the red sheen of the sunset hitting the downtown Boston city skyline

See why I say Boston is genuinely a great summertime destination? The capital city of Massachusetts has a lot going for it with stunning backdrops to match. Such a colorful place with dynamic landscapes and a variety of activities and yummy food!

How do you feel about summer in Boston? Have you been during this time? If so, what did you like about it, and do you have anything to add to my list? If not, which things from the list would you most like to see? Remember, I do love hearing from you so let me know below!

‘Til next time…

Trimm Travels,