Bunker Hill Memorial in Boston

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Perfect Weekend In Boston: 3 Day Itinerary For First Time Visitors

Looking for the best things to do in Boston, aka “Beantown”? It might be best known for its clam chowder, Fenway Park, baked beans, strong Irish ties, the Boston Marathon, and some of the best universities in the United States. If I sparked your interest, then continue reading to plan an amazing weekend in Boston!

Wandering along the cobblestoned streets and squares, you get the big city feel of Boston with its mix of old and new that complement each other well.

With numerous outdoor recreation options, fantastic restaurants, shopping, and entertainment, you will find plenty of Boston attractions to see.

I have been to Boston countless times and it is a city where you can find new things to do for every type of traveler no matter the season.

The beautifully manicured inner courtyard of the Public Library in Boston with one of the best things to do on a weekend in Boston.

In this post I’ll provide the perfect 3 day Boston itinerary including where to stay, what to eat, and tips for your visit.

Tip: If you plan to see many Boston attractions, consider getting a Go Boston Pass which has up to 55% off several top attractions. You can customize it for 1, 2, 3, 5, and 7 days depending on how long your stay is.

Or use the Hop-On Hop-Off Trolley Tour to get around to all the top places to visit in Boston!

A Little History On Boston

No, I won’t bore you with a history lesson but there are some fun and unique points of interest in Boston’s history. You might be wondering what is with the nickname “Beantown”?

Well, when the city was getting its start, sailors coming into the bay noticed that Bostonians loved their beans baked in molasses. As they say, the rest is history…

An art mural with the word Boston on a red brick wall, just one of the top things to see on a Boston itinerary.

I’m really summing it up when I say that Boston is the location of several events that led to the American Revolution and eventually America’s independence from the British on July 4th, 1776.

It played a very influential part in the success of the American Revolution.

Boston is the capital of Massachusetts and part of the original 13 colonies established in what is now the United States. Following the pattern of being one of the first, Boston has the first:

  • Subway in the United States
  • Public park in the U.S.
  • Fig Newton cookies were named after the neighborhood of Newton (love these)!
  • Dunkin Donuts is from here
  • Baseball park in America
  • Home to the Boston Cream Pie creation
  • You won’t find a “Happy Hour” in Boston, against the law…
  • Boston was named after a town in England

Where To Stay In Boston

Determining where to stay in Boston might depend on what you are there for or what you want to see the most. For example, if you are there for work staying near the conference center might be most ideal.

There are several great areas to stay in but if you are on vacation then I recommend staying in or near Back Bay, Boston Common or Theater District.

These three areas are centrally located in downtown Boston and close to the majority of sites to see. A more cost-effective alternative that isn’t too far and in a lovely area is Cambridge. Cambridge is the neighborhood where Harvard University is along the Charles River.

Westin Copley Square

Fairmont Copley Plaza

Four Seasons Boston

The Godfrey Hotel Boston

Discover Fun Tours In Boston To Take!

The Best Boston Itinerary

Weekend In Boston Day 1

Boston Common

Boston Common is such an excellent spot to start your tour of Boston as it is the most central area of the city and a beautiful park.

It also happens to be the oldest city park in the United States, dating back to 1634.

The park has served as a gathering place for the people, a grazing location for cows, and even the site of public hangings up until the early 1800s.

A wide paved path lined with trees through Boston Common which is a lush and green park that is one of the top Boston attractions to see.

A round ornate metal plaque on the ground in Boston Common has the wording The Boston Freedom Trail as a marker to where it begins.

Today the 50-acre park is a great place to go for a walk, get in a run or play ball games in the green oasis amidst the bustling city.

What makes Boston Common a little more famous is that it is the beginning of the Freedom Trail.

I’ll talk more about the Boston Freedom Trail as I go through the itinerary but make sure to walk over to see the Massachusetts State House along the Beacon Street side of the park.

You can’t miss it with its dome that is gilded in gold. It is a gorgeous building as it should be since it is the state capital.

Follow the red brick path to stay on the Freedom Trail in the center of Boston.

The beautiful Massachusetts State House with its dome top is one of the best things to do in Boston.

Note: For the longest time I referred to it as “Boston Commons” but only recently realized there is no “s”! It is Boston Common.

Tip: You can find a Boston Visitor Center along the edge of the park on the corner of Tremont Street and Temple Place.

Public Garden

Directly across from Boston Common is the Public Garden with Charles Street separating the two.

Established in 1837, a few hundred years after Boston Common the Public Garden is a favorite spot of mine.

There is a charming and tranquil atmosphere with ponds, flowers, bridges, swans, and plenty of areas to have a picnic.

It looks like it could be a movie set and actually has been the backdrop for many shows and movies.

The Public Garden is the perfect place for a picnic as this woman sitting next to the pond, trees surrounding with high rise buildings and a steeple in the distance in Boston.

Walking over the Lagoon Bridge in Public Garden in the heart of Boston, MA.

A Swan boat ride tour on the lagoon in the Public Garden in downtown Boston, MA.

Designed with a Victoria-era feel, you can not only see real swans and ducks but take a relaxing ride on a Swan Boat.

It takes you on a tour of the lagoon, under the Lagoon Bridge, and around Mallard Island.

If you have the Go Boston Pass then a Swan Boat Tour is included!

A swan boat tour on the lagoon in the Public Garden about to go under the bridge with the Boston city skyline in distance.

Another popular site to see especially with kids is the “Make Way For Ducklings” statues.

It is a momma duck with her ducklings located near the corner of Charles St and Beacon St area of the park.

The statues are inspired by the children’s book “Make Way For Ducklings” by Robert McCloskey. It is about a duck family living in the park.

Boston Freedom Trail

The Freedom Trail is a 2.5-mile long path that takes you on a trek into America’s history seeing the most notable landmarks in downtown Boston.

But what exactly is the Boston Freedom Trail you might ask?

The trail takes you past 16 important sites from the American Revolution War that started in Boston in 1775.

The red bricks will lead you the entire 2.5 miles of the Boston Freedom Trail
The red bricks will lead you the entire 2.5 miles of the Freedom Trail
The Old South Meeting House is one of the 16 stops on the Boston Freedom Trail in Boston, Massachusetts.
The Old South Meeting House is one of the 16 stops on the trail

For those that need brushing up on history, the American Revolution was the war that established the United States.

It was the independence from Great Britain and overthrowing British rule over the 13 colonies.

Most people start the walk at Boston Common and end it at Bunker Hill although you could easily do it in reverse.

Walking the Freedom Trail is go at your own pace unless you are taking a tour.

If you plan to stop and go inside some of the attractions then I would allow between 4 – 6 hours including a stop for lunch.

A metal plate on a section of the Boston Freedom Trail marking the site of the Boston Massacre.
This marks the site of the Boston Massacre
The Old State House nestled among the modern buildings of Boston along the Boston Freedom Trail.
The Old State House nestled among the modern buildings

But you could easily take your time and spread out over two days depending on what interests you.

I will select a handful of the sites that should be a must to see but here are all 16 in order starting from Boston Common.

  • Boston Common
  • Massachusetts State House
  • Park Street Church
  • Granary Burying Ground
  • King’s Chapel Burying Ground
  • Benjamin Franklin Statue
  • Old Corner Bookstore
  • Old South Meeting House
  • The Old State House
  • Site of Boston Massacre
  • Faneuil Hall
  • Paul Revere House
  • Old North Church
  • Copp’s Hill Burying Ground
  • USS Constitution
  • Bunker Hill Monument

Tip: Grab a free map of the Freedom Trail from the Visitor Center in Boston Common or Faneuil Hall.

If you prefer taking a guided walking tour that focuses on providing you with plenty of history of Boston then consider signing up for the Boston Historic Walking Tour!

Note: No map, no problem! Follow the red brick trail from one site to another that is clearly marked. You can’t miss it and likely many others will be following it too!

Granary Burying Ground

As mentioned above as part of the Freedom Trail, this is one stop not to miss. It might sound odd but I think it is such a beautiful cemetery.

There is obviously a darkness to being around so many buried people but it makes me wonder about the lives of those that call it home. If only we could hear their stories!

Established in 1660, Granary Burying Ground has some very well-known citizens resting here.

Rows of old headstone markers that are worn over the years in the Granary Burying Ground which dates back to 1660.

Rows of short and old headstone markers with small American Flags stuck in the grass in between at the Granary Burying Ground in Boston.

You can see the graves of Benjamin Franklin’s parents, Paul Revere, John Hancock, Samuel Adams, and those who lost their lives in the Boston Massacre.

It is estimated that there are over 5,000 people buried here but not the same amount of headstones.

The headstones are said to have been moved around over the years. You can see the age of the headstones as many are remarkably simple with the engraving barely visible.

Book Your Ghosts & Gravestones Tour Today!

Faneuil Hall

Built in 1742, Faneuil Hall is famous for the fact that it is the site of America’s first town meeting and also known as the “home of free speech”.

It was a place where people could come together to speak their minds and served as a marketplace.

Two notable events in 1764 were the protests against the Sugar Act and the Stamp Act.

People walking in front of Quincy Market with a large American Flag hanging and has many great places to eat inside.

Today, Faneuil Hall still serves as a marketplace with places to eat and plenty of shopping to do.

This is a great place to take a break and grab some lunch as there are many options to choose from.

Although a separate building, choose from several food options in the Quincy Market building.

The Quincy Market is right behind Faneuil Hall and all part of the Faneuil Hall Marketplace. Although the Quincy Market is much newer than Faneuil, it is still a notable building to admire.

If you are a seafood lover then be prepared to get a cup of clam chowder or fresh oysters!

The front view of Union Oyster House made of red brick and is one of the oldest restaurants in the U.S.!

Make a note of looking up to see the grasshopper copper weathervane on the top of Faneuil Hall. Why a grasshopper?

Well when Peter Faneuil built it, he basically copied the one above London’s Royal Exchange. The grasshopper symbolizes “commerce” which has taken place at Faneuil Hall all these years!

Tip: Another great lunch spot is the Union Oyster House which is along the Freedom Trail a few minutes past Faneuil Hall.

Established in 1826, the “ye olde” Union Oyster House has a great atmosphere and great clam chowder. It is said to be one of the oldest operating restaurants in the U.S..

Explore The Freedom Trail Stops On This Tour!

Paul Revere’s House

After filling your belly with New England specialties, continue on the Freedom Trail to visit Paul Revere’s House.

Thought to be built in 1680, this house is where the famous Paul Revere lived and happens to be the oldest building in downtown Boston.

Paul Revere was one of the most well-known patriots during the American Revolution.

He was also a businessman and a craftsman that is famous for his midnight ride on a horse in 1775 to alert his fellow colonists that the “British were coming”.

The exterior entrance of Paul Revere's old home made all in red brick in Boston, MA.

Statue of Paul Revere with the Old North Church in the background in Boston.

His actions (and others that were never mentioned) gave the American colonists an advantage and eventually what assisted in America’s Independence from Britain.

You can see the monument or statue of Paul Revere riding his horse in the nearby Paul Revere Mall.

It is on the opposite end of the mall (park) in front of the Old North Church along Hanover Street.

Tip: With the purchase of the Go Boston Pass, your ticket into Paul Revere’s House is included!

Bunker Hill

After you cross over the Charlestown Bridge (that crosses the Charles River), make your way over to the Bunker Hill Monument.

As you walk over to the monument at Bunker Hill, don’t miss out on passing through Winthrop Square.

Winthrop Square is a charming little park that has very adorable houses lined around it.

About two blocks from Winthrop Square you will see the prominent Bunker Hill Monument standing atop “Bunker Hill”.

View of Bunker Hill, the harbor with boats from the Charlestown Bridge in Boston.

The charming Winthrop Square with large grassy area, planters with flowers and a statue in the center in Boston, MA.

A large American flag hanging on an old red brick house in Boston, MA.

This hill really is Breed’s Hill but someone during that time got the hills mixed and well the name Bunker stuck…

The monument rests on the site of where the first battle sparking the American Revolution began and known as “The Battle of Bunker Hill”.

This battle set the tone of the war and showed that the colonists had the ability to take on the British and win.

The Bunker Hill Monument is an obelisk standing at 221-feet tall and open for the public to climb the 294 steps.

The tall obelisk shape of the Bunker Hill Monument is almost 300 steps to the top in Boston, MA.

Admiring the Bunker Hill monument up on the hill on a grassy area with an iron rod fence in the foreground..

There is no elevator so be prepared to burn some calories from that clam chowder!

There is also a museum across the street in case you want to learn more about the battle here.

Boston’s North End

After visiting Bunker Hill and the USS Constitution, head back the way you came and go to Boston’s North End.

If you didn’t realize it, you walked through a portion of this Italian neighborhood earlier on the Freedom Trail.

The Skinny House is quite tiny in between two larger apartment buildings in the North End of Boston.

A wooden sign on the side of the Skinny House that says skinny house est 1862 and is one of the thinnest in the United States!

As you walk down Prince Street towards the heart of North End, take a few minutes to see Copp’s Hill Burying Ground (part of the Freedom Trail sites).

On the opposite side of the street enjoy the very slim or “Skinny House” that is a treat to see as one of the skinniest houses in the United States.

This is one of my favorite neighborhoods in Boston as it just has that historic feel to it and I can never get enough of cobblestoned streets!

This is a great place to grab some dinner especially if you have a weakness for Italian food or a Lobster Roll.

Beautiful architecture and windows on an old apartment building in the North End of Boston.

There is much debate on the best Lobster Roll in town but one of the best is at Neptune Oyster.

Come with patience and a snack in your bag as there will likely be a wait for this delicious meal.

Overall, this is a neighborhood to wander, get some awesome food, and follow the footsteps of history.

The front of Neptune's Oyster with its blue awning has the best Lobster Rolls in Boston.

Tip: Looking for some dessert? Meander over to Mike’s Pastry shop at 300 Hanover St. known for some of the best cannoli’s!

Explore The Best Tours In Boston!

Weekend In Boston Day 2

If you didn’t make it through all of the Freedom Trail then continue where you left off this morning. If you walked it all then continue on this Boston itinerary!

Beacon Hill

Even if you haven’t been to Boston, you will likely have seen photos of Beacon Hill.

It is photographed a lot for its incredible beauty and idyllic cobblestoned streets that you can’t help but smile as you walk along them.

The picturesque neighborhood is bordered by the Charles River on one side with Boston Common and North End on the other side.

This is a great area to start off your day by grabbing a coffee or breakfast and taking to the adorable streets bathed in charm.

Beacon Hill is the oldest neighborhood in Boston with visibly distinct red-bricked houses, wrought-iron touches, and the American Flag hanging proudly throughout.

Acorn Street is one of the most photogenic streets in America with its pedestrian only cobblestone street, brick homes and old street lanterns in Boston.

A very old American Flag hanging from the front a red brick and historic home on Acorn Street in Boston.

One of the most popular streets to walk through is Acorn Street. It is a short cobblestoned street that is probably one of the most photographed streets in the United States.

If you visit, do be respectful and not bother the residents or do a “photo shoot”. Admire, take a few photos and keep walking…

Another area to explore is Louisburg Square that is surrounded by some of the priciest homes in all of Boston. Not surprisingly there have been some famous residents in this posh neighborhood!

If you want to learn more about Beacon Hill’s fascinating history, read A Historic Stroll Thru Boston’s Beacon Hill.

There are so many interesting tidbits of history that you will love and have a greater appreciation for Beacon Hill.

Acorn Street is a beautiful cobblestone street in a historic area of Boston, MA.

Tip: If you plan on taking the Boston Historic Walking Tour then it will cover Beacon Hill on it!

Note: I found out after my last visit about the Gibson House which is an old house that is now a museum and showcases life back in the late 1800s and early 1900s.

Charles River Esplanade

When the weather is nice, one of the best places to visit in Boston is taking a stroll along the Charles River Esplanade.

The Esplanade is a 17-mile grassy stretch, an outdoor park, and paths for walking, running or riding a bike along the Charles River.

Not only do you get gorgeous views of the river but you can see boats sailing by and enjoy the breeze coming off the water.

And you can experience being on the Charles River with taking this fun tour by land and water!

The Charles River Esplanade in Boston is a great place to enjoy the lovely river views on a wooden dock and buildings on the other side.

A red lounger chair on the wooden deck along the Charles River in Boston on a sunny day.

During the summer months, you can even catch an outdoor concert or movie at the Hatch Shell.

Keep in mind, that there are only a few places to cross over the high trafficked Storrow Drive.

You can enter and leave any way you wish. I entered via the Charles Street bridge and exited on the Dartmouth Street bridge. It gave me the opportunity to enjoy a large section of the park.

View of the wide Charles River in Boston along the banks and looking out at the bridges and buildings on the other side.

There is an inner lagoon next to the Charles river that is a tranquil spot with a beautiful reflection of the trees in the water in Boston.

The most popular pedestrian bridges to cross near downtown are:

  • Blossom Street where there is a pedestrian bridge from the Mass General Hospital campus.
  • Charles Street which will drop you off near the Community Boating Building.
  • Arlington Street takes you across the Arthur Fielder pedestrian bridge and drops you near the Hatch Shell.
  • Dartmouth Street that will lead you to the lagoon prior to getting to the river’s edge.

Tip: With the Go Boston Pass, a Charles River Cruise is included in the pass. Or consider this fun and quirky way to cruise the river and more!

Newbury Street

As you leave the Charles River Esplanade, take a quick tour of Marlborough Street which runs parallel to the river. Marlborough is the first main street you will cross over after Storrow Drive.

You will get to view beautifully crafted brownstones (houses) as you walk. It is residential so there isn’t anything to do but admire the scenic street.

Next, make your way over to Newbury Street which is an extremely popular street and an excellent area to grab some lunch. Newbury Street runs parallel to Marlborough Street separated by Commonwealth Ave.

Known for shopping and restaurants Newbury Street is an enchanting area to relax and indulge a bit.

One place that I really enjoyed eating at is Stephanie’s on Newbury. It is a prime spot to sit on the outdoor patio weather permitting and do some people watching.

They serve what is called upscale American food with salads, burgers, clam chowder, and plenty more to satisfy everyone in the group!

Copley Square

After lunch head over to Copley Square that is a public area in what is known as the Back Bay neighborhood.

It is also just a street away from Newbury Street so it is close by! It is surrounded by Trinity Church, The Boston Library, Old South Church, and hotels.

Trinity Church across Copley Square with a large grassy park in front in the center of downtown Boston.

Copley Square has an artsy atmosphere with street performers entertaining you in every direction. It might have something to do with the square being named after an artist John Singleton Copley.

During spring through fall, it is a great place to get takeout lunch and enjoy watching people passing by and you might find a farmers market here!

Trinity Church

Trinity Church was built in 1733 but later burned down in the Great Fire of Boston in 1872.

The church you see today was completed in 1877 in a Richardsonian Romanesque architectural style.

I love seeing the history of the old church with the modern buildings surrounding it.

Trinity Church is a beautiful church along Copley Square in the center of Boston.

Boston Public Library

Although I have been to Boston countless times, I hadn’t ever been to the Boston Library until my most recent visit.

Several people told me it was stunning inside and worth visiting. Let’s just say I am so glad I listened to them!

The front entrance of the Boston Public Library with flags hanging above the entrance.

The grand staircase that is stunning of the Boston Public Library with floor and walls covered in tan colored marble.

The Boston Public Library might be my new favorite spot in Boston as I am a huge book lover.

The interior looks more like a palace than the libraries I’m used to seeing. It has a well-manicured outdoor courtyard with seating to relax with a book or just enjoy the peace.

Opening to the public in 1854, it is the third-largest library in the United States.

You will see marble staircases, chandeliers, and incredibly large statues of lions! If you feel like a caffeine pick me up or a bite to eat, there is a tea room and café that you can pop into.

A lion statue looks on guard as it greets you to the library as you go up the main staircase.

The gorgeously manicured and peaceful interior courtyard at the Public Library in Boston.

The historic and large reading room in the Boston Public Library with its arched ceilings with detailed carvings in it and small green lamps on each reading table.

You are free to walk around and view the various rooms and their grandeur.

But if you would like to learn more about the history, then consider taking an art and architecture tour that is free and lasts about an hour.

Prudential Observatory

In the Prudential Center, there are many options for shopping and eating but take a ride up to the Prudential Skywalk Observatory for epic views of downtown Boston.

On the 50th floor of the Prudential building, the Skywalk Observation deck offers 360-degree views of the city below.

With the Go Boston Pass, your ticket up to the Skywalk Observatory is included in the pass!

And it is a great way to spend on your second day of sightseeing using this Boston itinerary.

Depending on the time of day, you might want to visit the Reflection Pool located behind the Prudential Center and next to the Christian Science Plaza.

The Reflection Pool after a summer rain with the Prudential Building in the background among other tall buildings in Boston.

The Prudential Building is the square high-rise on the left among taller buildings in downtown Boston.

The Reflection Pool looks gorgeous in the afternoon with the Prudential building in the background. If you love taking photographs then you will love it.

There are numerous restaurants to choose from in and near the Prudential building but one I love that isn’t too far is The Salty Pig (130 Dartmouth St).

Prudential Address: 800 Boylston St, Boston

Reflection Pool Address: 93-105 Falmouth Street, Boston

Explore Fun Tours In Boston To Take!

Weekend In Boston Day 3

Start out your third day in Boston with a good cup of coffee and a yummy bite to eat at Tatte Bakery & Café. There are several locations around the city so you should have no trouble finding one close to your hotel.

Cambridge

Although not technically in the city of Boston, Cambridge is just across the Charles River. As it is so close and easy to get to, I include it in the best things to do in Boston.

Cambridge is home to Harvard University and MIT which are some of the best universities in the United States and very elite.

Oh and if you haven’t had your coffee and breakfast yet, there is a Tatte Bakery & Café in Cambridge too (1288 Massachusetts Ave, Cambridge).

The grassy area of Harvard Yard at Harvard University in Cambridge, Boston.

A historic red-bricked building on the campus of Harvard University in Boston.

I wouldn’t say there is a ton to do in Cambridge but I really enjoy walking around Harvard’s campus as the buildings are some of the oldest in America.

Harvard was established in 1636 and no shock that it is the first university in the United States.

As you cross Harvard Yard, notice all the aged red-bricked buildings surrounding the Yard.

To find out more tidbits of fascinating history, consider taking a Crimson Key Tour. The hour-long tour is free of charge so why not!

An old historic building with a tall steeple at Harvard the first university in the United States.

View of the Charles River with arched bridge on beautiful day from the Cambridge side in Boston.

After passing through Harvard Square outside of campus, you can see Harvard crew teams practicing on the Charles River.

You will most likely see in the spring and fall as Harvard is quite famous for their crew!

Tip: If you are ready for lunch, get what might be one of the best burgers at Mr. Bartley’s Burgers and also featured in the movies Good Will Hunting and The Social Network.

Fenway Park

If you plan to visit Boston between the months of April and September seeing a live Boston Red Sox baseball game at the iconic Fenway Park is a must.

Fenway Park is the oldest ballpark in the United States built in 1912 and has an Americana nostalgia to it.

Looking at the huge sign for the Boston Red Sox at the iconic Fenway Ballpark is the oldest in the U.S.

Even if there are no games during your visit, you can walk around the ballpark and take in the history of this famous landmark.

It has even been nicknamed “America’s Most Beloved Ballpark”.

If you want to take a Fenway Park tour (it’s included with the Go Boston Pass) and learn about the history, tours are offered year-round but times vary depending on the game schedule.

About a 5-10 minute walk from Fenway is the Back Bay Fens that is an urban park. So, if you are looking for a bit of nature this is the spot as there is also a rose garden to wander in.

Address: 4 Jersey Street, Boston

Samuel Adams Brewery

If you like beer and the making of it, then you will enjoy visiting the Samuel Adams Brewery just minutes from downtown Boston.

Most refer to the beer as “Sam Adams” for short and named after one of the founding fathers of the United States.

Hop in an Uber, Lyft or take the T’s (metro) Orange line to the Stony Brook Station and get there in minutes.

The brewery might be the most famous for its Boston Lager using a recipe that goes back many generations of Jim Koch’s family. Koch started this brewery out of his home and opened it to the public in 1988.

Take a tour of the brewery to learn how the beer is made and get three tastings at the end! The tours are Monday through Saturday.

But if you don’t have time to take a tour and just want to taste, there are two Tap Rooms. One is located at the brewery and the other is the Faneuil Hall Tap Room at 60 State Street, Boston.

Address: 30 Germania Street, Boston. For current Brewery and Tap Room hours, visit their website, here. Or if you purchase the Go Boston Pass then your tour ticket will be included!

Additional Boston Activities

At this point, you have completed the best things to do in Boston itinerary! If you saw everything and have more time, consider visiting some bonus suggestions of places to visit in Boston.

  • Boston Tea Party Museum & Ships – Visiting this museum on the water will take you back into time of the famous event that altered American history. The night of destroying “the tea” is re-enacted as a rebellious period in 1773 leading up to the American Revolution.
  • Isabella Stewart Gardner Museum – This former house of Isabella Stewart Gardner was an art collector who happened to have incredible pieces, some of which are reportedly stolen. Although the crimes have not been solved, the picturesque home looks more like a Venetian palace (included with the Go Boston Pass).

         Note: The museum is on the edge of Back Bay Fens and near Fenway Ballpark.

  • Rose Kennedy Greenway – An urban oasis along the Waterfront, North End, and the Financial District with garden landscapes, beer gardens, food trucks, and plenty of open space to walk.
  • New England Aquarium – Located on the wharf and close to the Greenway above, this is a popular thing to do with kids (included with the Go Boston Pass).
  • Duck Boat Tour – It might be a little bit corny but the Duck Tours are fun in that it takes you on a tour of Boston both by land and water! Yep, it is a special type of vehicle that can drive right into the water and float (included with the Go Boston Pass).
  • Go On A Boston Harbor Sunset Cruise – No better way to see the city skyline than taking a sunset cruise in Boston Harbor.
  • Whale Watching Excursion – Visiting in May – October? Consider taking this catamaran cruise to see whales in the wild!

Best Boston Food Tours

If you are a foodie and want to check out the best foods that Boston is known for then consider one of these tasty food tours.

North End Secret Food Tour – Take this 3 hr food tour in the iconic North End neighborhood to sample the best bites this area of town is famous for!

Boston’s North End Pizza, Meats & Cheese Tour – Indulge in the yummiest foods centered around pizza, meats, and cheese in the North End neighborhood of Boston!

Boston Seafood Tasting & History Tour – Calling all seafood lovers! Don’t miss out on sampling the best lobster roll, clam chowder and more that Boston is known for.

Historic Taverns of Boston Tour – Not quite food, but this cool tour takes you to some of Boston’s oldest bars paired with lots of history and fascinating stories!

Best Places To Eat in Boston

Boston has so many excellent places to eat that I can’t possibly name them all here! Although you can find any cuisine in Boston, it is probably best known for its seafood and Italian food.

And make sure you try a Lobster Roll which is a New England favorite and one I miss having in California.

A yummy Lobster Roll at The Hourly Oyster House in Boston, MA.

I have eaten at all of these restaurants except for the rooftop bar and can highly recommend them based on my experience. Bon appetite!

  • Union Oyster House – 41 Union Street, Boston
  • Neptune Oyster – 63 Salem Street, Boston
  • The Daily Catch – 323 Hanover Street, Boston
  • Giacomo’s Restaurant – 365 Hanover Street, Boston
  • Mike’s Pastry – 300 Hanover Street, Boston
  • Stephanie’s on Newbury – 190 Newbury Street, Boston
  • The Salty Pig – 130 Dartmouth Street, Boston
  • Sweetgreen – 659 Boylston Street, Boston
  • Life and Alive Organic Café – 431 Boylston Street, Boston
  • Tatte Coffee – several locations
  • Lolita’s Cocina & Tequila – 271 Dartmouth Street, Boston
  • Liberty Hotel – Used to be an old jail and a great place for drinks! 215 Charles Street, Boston
  • Wagamamma – 100 North Avenue, Boston (Seaport neighborhood)
  • Mr. Bartley’s Burgers – 1246 Massachusetts Ave, Cambridge
  • The Hourly Oyster House – 15 Dunster Street, Cambridge
  • Rooftop @ Revere Hotel – drinks with a view at this rooftop bar! 200 Stuart Street
  • Dona Habana – 811 Massachusetts Ave, Boston

Top Overall Boston Tours To Take

Guided Freedom Trail Walking Tour – Stroll through Boston’s history as a guide leads you along the Freedom Trail and learn all about Boston’s start!

Boston Ghosts & Gravestones Tour – Listen to haunted ghost stories as you visit gravestones several hundred years old on this spooky night tour!

Fenway Park Guided Tour – Explore this iconic baseball park home to the Boston Red Sox, the oldest ballpark in the United States!

Boston Harbor Sunset Cruise – Enjoy the spectacular views of Boston’s city skyline at sunset in Boston Harbor!

Boston Duck Tour – See Boston by land and water as this quirky and fun vehicle takes you to the most popular Boston attractions.

Whale Watching on A Catamaran Excursion – From May – October, hop on a whale watching experience aboard a catamaran to view whales in the wild!

Map Of Boston’s Must-See Spots

Here is a map of all the sights listed below to make planning easier for you!

Trip map created with Wanderlog, a road trip planner

Where Is Boston?

Boston is the capital of Massachusetts and sits on the east coast of the United States. It is located in the region referred to as New England.

New England as a whole is known for its vibrant and breathtaking fall foliage during the September and October months.

The city of Boston is an excellent city to explore with its position right along the ocean and the Charles River.

Massachusetts is north of Connecticut and Rhode Island, east of New York, and south of Vermont and New Hampshire. As you can see it has a close proximity to many other states!

If you are flying into Boston, book your flight to Boston Logan International Airport (BOS) which is about 15 – 30 minutes depending on traffic from downtown Boston.

Why not search for the best flight deals and book your trip today!

How To Get Around Boston

Boston is a city that is easy to get around on foot if you are focusing on the downtown area.

Plus, walking is the best way to see unique places on your way to your next destination. For those locations that are maybe too far apart, I recommend taking the T.

The T is Boston’s subway or metro system that can take you to where you need to go both near and far. For a detailed map of the T lines, you can get a map from a Visitor Center or view on MBTA’s website.

While you are in the city I would discourage getting a rental car as you won’t need one and parking is very expensive.

If you do plan to take some day trips then maybe add those on at the end of your trip or vice versa and rent a car then. Find the best car rental deals here!

Another great option for getting around is to purchase a ticket for the Boston Trolley Hop-On Hop-Off.

When To Visit Boston

The best time to visit Boston is from the spring through fall months. That is when the weather is at its prime and no fear of it being freezing cold.

Boston can have cold and snowy winters so unless you have an event to attend, I would probably stay away during those months.

Spring through Fall, Boston is a perfect place to visit
Spring through Fall, Boston is a perfect place to visit

If you have ever been to New York City or Philadelphia, the weather is pretty similar for the most part. Like any other city, the summer months can get crowded but the weather is ideal for so many outdoor activities.

The fall months are some of my favorites months as the temperatures are still nice, fewer crowds and you might get to see the leaves begin to change colors on the trees.

New England is definitely the place to be if you want to go leaf-peeping in autumn!

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Vanessa Shields

Vanessa Shields is the founder of Traveling Ness helping people with trip ideas, itineraries, travel planning, and boosting confidence for female travelers to take a solo trip. She has been a travel writer and content creator since 2019.

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32 Comments

  1. Boston happens to be my favorite US city to visit! Your post is fantastic and very detailed! I enjoyed your food suggestions as I’ve eaten at several of those with the Daily Catch being our #1 when we visit! We love to go to Mike’s and grab some dessert and head to the Boston Common and sit, eat and people watch. We did the Bunker Hill Monument for the first time on our last visit and boy, was it tough!
    Thanks for sharing!

    1. Thank you so much Miri! Boston is indeed and wonderful city and glad you agree. Congrats on climbing Bunker Hill, that is an accomplishment! 🙂

  2. I’m from Boston and grew up there my entire life so I loveee that you included a couple of my faves (the library and the North End!) This post seriously makes me miss home so so much…

    1. Yes, the library and North End are some of my favorite spots too as they are so charming. That is really cool that you grew up there as it is such a great city! 🙂

  3. My father in law is from Boston and I’ve been wanting to go there for a while but had no idea there was so much to do. The courtyard in the public library looks incredible, it reminds me of somewhere in Italy or Spain! Thanks for sharing, I’ll definitely be keeping this for when I eventually make it over there!

    1. Oh you have such a great excuse to go visit if you have family there. Until I started visiting Boston, I wasn’t aware of how much there is to do too. It is one of those cities that surprises you and I hope you get the opportunity to go one day soon. I completely agree, the library really does look like it could be set in Italy or Spain! 🙂

    1. Well, I hope you get the chance to go soon once travel is possible. You will love it if you enjoy history for sure! 🙂

  4. Thank you for the awesome guide. I look forward to visiting Boston once everything is back to normal 🙂

    1. You’re welcome! I hope you can use this guide when you get the opportunity to visit Boston! 🙂

    1. You’re welcome! Boston is a great city especially if you like seafood and history. Have a great time when you do make it there! 🙂

  5. Thanks for all the Boston suggestions! As a native Rhode Islander Boston was always the big city for me growing up! I haven’t been back to visit much as an adult, and your post is inspiring me to plan a long overdue visit. Also, I never knew all the Boston firsts!

    1. I’m so happy to hear even from a pretty close neighbor you learned some new things! It will be fun to go back and explore as an adult and see it in a new way! 🙂

    1. Thank you, I’m glad you enjoyed reading the guide! Living in NYC is a great nearby getaway that isn’t too far too explore. I used to go to Boston for work all the time when I lived in NYC and miss both cities a lot! 🙂

  6. I love Boston. I went there for the first time in 2012 and say I would go back in Autumn. I have yet to return so this post is bringing back good memories. Thanks for sharing this great guide 🙂

    1. I’m so glad reading this brought back great memories of Boston! I agree autumn is my favorite time to visit as you have great weather and fall foliage. I hope you get to go back and relive those memories and more soon. 🙂

  7. I LOVE Boston!! We’ve been several times and still haven’t done half of these things! We definitely need more time to explore fully!

    1. I agree Boston is such an awesome city! Now you have a great excuse to go back and see more! 🙂

  8. I just realised I knew so little about Boston. I didn’t even know Harvard was there. It’s a beautiful city with great architecture. Trinity church and the library are right up my street. Beata always says she would like to visit Boston. I can see why now. Another top & complete guide Vanessa.

    1. Thank you John! It doesn’t get as much attention as New York but is a beautiful city with so much to do. The library is unbelievably gorgeous and I am sure you and Beata would enjoy visiting! 🙂

  9. What a great Boston post! I’ve visited a few times and done the freedom trail. There’s so much history there, I absolutely love it. Good to see Neptune Oyster and Mikes Pastry on your list! My absolute favorite spots 🙂

    1. Thanks Lannie! There really is more history than at first glance and a fun city to explore. Omg yes, the best Lobster Roll at Neptune Oyster! I would fly in just for that! 🙂

  10. I always wondered why Boston was called Beantown, now I know. What a beautiful place and so many firsts! I hope to visit one day and will definitely head to the library, what a stunning building. Thank you for sharing your itinerary, going to pin it for future reference.

    1. Haha, yes they liked their beans back then! I think you would definitely enjoy the library and seeing the sites along the Freedom Trrail! 🙂

  11. What a wonderfully comprehensive itinerary, Vanessa! I’ve wanted to visit Boston for years but never managed to make the trip from DC when I lived there. Now it’s a bit further away… so I’m pinning this itinerary for later! That historical walking tour looks fantastic and I love clam chowder!

    1. Thanks Becky! I had the opposite problem, I lived in NYC and kept meaning to visit and tour DC other than being there for a day or two for work. Still on my list! Glad the itinerary sparked your desire to go visit one day! 🙂

  12. When I was living in the US, I would go to Boston quite often, and yet a lot of the things you have on your list, I haven’t done! I had no idea about the Skinny house! I learned a lot with this article haha, I feel a bit ashamed as a New Englander. Next time I’m there, I need to use your itinerary to actually go out and experience the city a bit more. Thanks for putting this together.

    1. Haha that’s too funny! Don’t worry, I am still learning about places in California where I am from. It takes time to see everything and I think when we are from a place we take it for granted. At least that is how I am at home. I’m so glad to hear there are new spots for you to explore on your next visit! 🙂

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