Best 2 Day Boston Itinerary: The Perfect Weekend

Boston, Massachusetts. A city that is rich in American history and has a culture of itself. Everywhere you look in the city, it reminds you of the pride of the people that live in Boston. This 2 Day Boston Itinerary will guide you through the best parts of what makes Boston, Boston.

Boston is the capital of Massachusetts and is located in the New England region. When you hear Boston, what comes to mind? Early American history, sports, the accent, or the seafood? Maybe it is all of it. All of these combined are what make Boston a truly unique city to visit.

Boston has a lot to offer as a city. You will not have a hard time finding something to do or see. From all the historical Boston sites to Fenway, Boston will make you want to stay longer to enjoy everything it offers. Using this 2 day Boston itinerary will help you make the most of your trip.

2 Day Boston Itinerary

There is a lot to choose from when spending time in Boston on what to see and do. This 2 Day Boston itinerary will hopefully help you be able to structure your trip and time in the best way possible.

Getting to where you want to go in Boston is not that hard. Boston is a very walkable city and has a great public transportation system called the Massachusetts Bay Transportation Authority. You will find that you can get anywhere you want without spending a lot of money this way.

Day 1: 2 Day Boston Itinerary

Arrive at Boston Logan International Airport and collect your baggage. I recommend not renting a car because Boston’s public transportation is great. Make your way out to be picked up by the Silver Line (Bus) that will take you to South Station in Downtown Boston.

Once at South Station, you will want to study “The T” map to figure out how to get to where you want to go. You will need to jump on the Red Line and connect somewhere else. Otherwise, take the Red Line to where you need to go for where your hotel is.

Once you check in to your room and are ready to head out, grab a bite to eat first. You will be doing a lot of walking. Depending on your time, grab what you like for food. After you are finished eating, it is time to get back on “The T”. Head to the Park St. and stop on either the Green Line or Red Line.

There will be a big park area once you exit the train stop. It will be Boston Public Garden and Boston Common right next to each other. Head over to The Boston Public Garden first.

Boston Public Garden

Welcome to America’s first public garden. The park, with Boston Common, is the northern part of the Emerald Necklace, which is a string of parks connected by parkways and waterways.

Boston Public Garden is designed in an English landscape garden style that has a pond and many different types of plants and trees. The garden is great for walking around and relaxing.

Make sure to check out the Swan Boats in the pond. Take a short trip on them to relax as you take in the views of the garden. These boats have been famous in Boston Public Garden for some time now.

While here, make sure to seek out the “Make Way for Ducklings” statues. These are statues that were made from the classic children’s book by Robert McCloskey. The book is about a duck family that makes their home in the Boston Public Garden. The statues are of Mrs. Mallard and her 8 ducklings, Jack, Kack, Lack, Mack, Nack, Ouack, Pack, and Quack.

2 Day Boston Itinerary: The Freedom Trail

The Freedom Trail in Boston is a 2.5-mile trail that connects 16 national historic sites that helped formed The United States of America. This walk takes you through more than 250 years of history that stretches throughout Boston. It is a unique historical trail that has museums, churches, meeting houses, burial grounds, parks, a ship, and historic markers. Doing this trail really helps to make your 2 day Boston itinerary amazing.

You are easily able to follow the Freedom Trail by the red brick that leads you around the city. The Freedom Trail will take you through the footsteps of those who helped create a new nation and changed the world dramatically. Enjoy this attraction that brings in over 4 million people annually to walk the Freedom Trail.

1. Boston Common

The beginning section of the Freedom Trail is in Boston Common. It starts at the visitor’s center in the Common. Boston Common is adjacent to Boston Public Garden and was established in 1634. The Common is the oldest city park in The United States of America.

Puritan colonists originally purchased the land rights to the Common. This spot was used for punishments that included a whipping post, pillory, and stocks. The location was used for hanging pirates, murderers, and witches.

Boston Common was used as a British camp in 1775 during the occupation of Boston. Over 1,000 British troops were stationed on the Common. From this spot, 3 brigades of British troops marched to the first battles of The American Revolutionary War at Lexington and Concord.

Today, Boston Common is used as a public park and hosts many events from concerts to ice skating in the winter. There have been many famous people who have given speeches on Boston Common. These people include Martin Luther King Jr, Pope John Paul II, and Mikhail Gorbachev.

Continue to follow the brick Freedom Trail to…

2. Massachusetts State House

The Massachusetts State House is the state capitol building and the seat of government for Massachusetts. This state house was completed in 1798 and has been upgraded several times. The Massachusetts State House is one of the oldest capitol buildings that are still in use.

This State House has a unique look to it with its gold dome. The dome was originally wood but then was covered in 1802 with copper by Paul Revere’s Revere Copper Company. Currently, the dome is gilded in 23K gold and was completed in 1997.

The Massachusetts State House has been the office of the elected Governor since its first one, John Hancock. It currently serves Massachusetts’ House of Representatives, Senate, and the Executive Branch. Oliver Wendell Holmes, an author, said that the State House is “The Hub of the Universe”.

Continue to follow the brick Freedom Trail to…

3. Park Street Church

Park Street Church is the third stop on the Freedom Trail and was founded in 1804. The church is an active evangelical congregational church.

The founding of Park Street Church was done with the “Religious Improvement Society” which began to meet weekly with prayers and lectures. It consisted of 26 members, most were from the Old South Meeting House. They were looking to creak a church with orthodox Trinitarian theology.

Park Street Church was once the tallest building in The United States from 1810 to 1828. The church’s steeple stands at 217 ft. When travelers were approaching Boston in the early 19th century, the church was the first landmark that they would see.

The song “My Country, ‘Tis of Thee” was performed for the first time at Park Street Church on July 4, 1831. This song is also known as “America”.

The church is next to the Granary Burying Ground, which is next on the Freedom Trail stops.

4. Granary Burying Ground

Granary Burying Ground was established in 1660 and is the third oldest burial ground in Boston. This site is named after the granary which stood next to it on the site of Park Street Church. It is believed that there are an estimated 5,000 Boston residents buried here.

Some major American historic figures are buried at Granary Burying Ground. When you first walk into the burial grounds, you will notice a large obelisk in the center. This is a marker for the graves of the parents of Benjamin Franklin.

While facing the Franklin obelisk, to the left you will notice another, smaller obelisk. This obelisk marks the location of the tomb of John Hancock.

When you first walk into the Granary Burying Ground and take the path right, you will come across two distinctive grave sites. One is a grave marker for the victims of the Boston Massacre. Next to this grave marker, is the grave site of Samuel Adams.

To the back of the burial grounds, there is a small grave site with a monument next to it. This is the grave site of Paul Revere.

It is great to stand in the presence of such people that helped create The United States of America. There are other members buried here such as Robert Treat Paine, James Otis, and Mother Goose.

Time to continue following the brick Freedom Trail to…

5. King’s Chapel and King’s Chapel Burying Ground

King’s Chapel is part of the Unitarian Universalist Association and is an American independent Christian Unitarian church. The church was founded in 1686 as the first Anglican Church in the New England colonies while King James II was reigning. The original church was made out of wood and in 1749 construction began on the current stone church.

In 1754, the stone church was completed and stood in the same spot as the original church. During The Revolutionary Way, the church was referred to as the “Stone Chapel” and was vacant. It reopened in 1782 after the war and became a Unitarian church. The church is still open for services.

King’s Chapel Burying Ground has no affiliation to the King’s Chapel even though they are right next to each other. This burial ground was founded in 1630 and is the first graveyard in Boston. Kings’ Chapel continued to be Boston’s only burial site for 30 years in the city.

The graveyard has more than 1,000 people buried in it. Here are a couple of the more famous residents that are buried here. They are John Winthrop, Massachusetts’s first Governor, and Mary Chilton, the first woman to step off the Mayflower onto New England soil.

Continue to follow the brick Freedom Trail to…

6. Boston Latin School Site/Benjamin Franklin Statue

The Boston Latin School was the first public school established in the colonies on April 23, 1635. Boston Latin School was a free school for boys, rich or poor, and girls had to attend private school while at home. The school was originally held at the first headmaster’s home until the completion of the first schoolhouse in 1645.

There is a mosaic and a statue of Benjamin Franklin, who was a student of the school, where the original school once stood. The original school was torn down in 1745 for the expansion of King’s Chapel. Boston Latin School has been in many different locations throughout the history of Boston. Today, it is located in the Fenway neighborhood.

Former students of the Boston Latin School include 5 signers of the Declaration of Independence. Those students were Benjamin Franklin, Samuel Adams, John Hancock, Robert Treat Paine, and William Hooper.

Continue to follow the brick Freedom Trail to…

7. Old Corner Bookstore

The Old Corner Bookstore that stands today was constructed in 1718. It is Boston’s oldest commercial building and was the home to the 19th-century publishers Ticknor and Fields.

This is the second building in this location. The first one was the home of Anne Hutchinson who was excommunicated and exiled in 1638 to Rhode Island. Anne and some of her children were slaughtered in New Netherland by the Siwanoy Tribe during Kieft’s War.

The original building burned down in the Great Boston Fire on October 2, 1711. It was rebuilt in 1718 and served as an apothecary on the first floor and a residence on the second floor.

It was first used as a bookstore in 1828. Ticknor and Fields, a publishing company used the building from 1832 to 1865. During this time it published great American works. Works such as Henry David Thoreau’s “Walden”, Nathaniel Hawthorne’s “The Scarlet Letter”, and Beecher Stowe’s “Uncle Tom’s Cabin”.

Continue to follow the brick Freedom Trail to…

8. Old South Meeting House

The Old South Meeting House was built in 1729 as a Puritan meeting house. This building being one of the earliest museums of American history is one of the most important sites in colonial America.

Members of the congregation included Samuel Adams and William Dawes, who rode along with Paul Revere in 1775 to Lexington. Benjamin Franklin along with his family were members of the Old South Meeting House.

This location is famous because it was used as the main stage for the protests against the British Crown in Boston from 1768 through 1775. The Old South Meeting House was where Patriots and Loyalists met to argue with each other. After the Boston Massacre in 1770, there were yearly meetings to commemorate the event.

The significant date that makes this place such an American historical site was a debate on December 16th, 1773. On this date, there was a significant debate over the taxation of tea that could not be settled. Samuel Adams gave the signal to The Sons of Liberty to head out to Griffin’s Wharf. This event came to be known as the Boston Tea Party and Patriots dumped 342 chests of tea into the harbor.

The Old South Meeting House was set to be demolished in 1872. Then a group of “twenty women of Boston” organized and was able to save the building. It has been open to the public as a museum since 1877 thanks to the effort of “twenty women of Boston”.

Continue to follow the brick Freedom Trail to…

9. Old State House

The Old State House was built in 1713 and served as Boston’s political, civic, and business center. This was the seat of Massachusetts’ General Court until 1798 when it moved to Massachusetts State House which was earlier on the Freedom Trail.

On March 5th, 1770 the Boston Massacre took place, which was right in front of the Old State House.

6 years later on July 18th, 1776, the Declaration of Independence was first read aloud in Boston from the east side balcony to crowds. It was read by Col. Thomas Crafts at 1 o’clock and was received very well because about two-thirds of Boston supported revolution and independence.

Old State House was used as Boston’s city hall from 1830-1841 before the city hall was moved to a new location. Then from 1841 to 1881, it was used for commercial business that included tailors, railroad offices, and more. After 1881 the building was turned into a museum.

In 1976, Queen Elizabeth II visited Boston and stood on the balcony, and made a speech.

If Paul Revere, Samuel Adams, and other patriots could have known that one day a British monarch would stand on the balcony of the Old State House, from which the Declaration of Independence was first read to the people of Boston, and be greeted in such kind and generous words…..well, I think they would have been extremely surprised! But perhaps they would also have been pleased to know that eventually we came together again as free peoples and friends to defend together the very ideals for which the American Revolution was fought.

Continue to follow the brick Freedom Trail to…

10. Boston Massacre Site

Right outside and in front of the Old State House is the site of the Boston Massacre. Today, there is a circular medallion on the ground that marks the location of the Boston Massacre.

The tensions were high already in Boston with the occupation of the British in 1768 with 2,000 troops. They were sent to help quell the citizen’s objection to the Townshend Acts. For two years it became worse and tensions were rising, then a spark happened.

The Incident

On March 5th, 1770, Private Hugh White with the British army was standing guard at the Old State House in the evening. A 13-year-old boy named, Edward Garrick, accused Captain-Lieutenant John Goldfinch of refusing to pay a bill to his master, who is a wigmaker. The Captain-Lieutenant ignored the boy because he paid the bill the previous day.

Private White called out to the boy to stop yelling and show respect for the officer. Garrick did not stop and in fact, stepped up to the Captain-Lieutenant and started to poke him in the chest with his finger. Private White seeing this came up and challenged Garrick and struck him in the head with his musket.

Seeing this, Garrick’s companion, Bartholomew Broaders started to argue with Private White and this produced a large crowd. As the evening grew, the crowd became larger and church bells rang out, which usually signified a fire. These bells attracted more people.

There were more than 50 Bostonians, led by Crispus Attucks, a mixed-raced former slave, around Private White. They were all throwing objects at him and trying to make him fire his musket. Captain Thomas Preston of the British army was alerted and went to the area with 6 soldiers.

They formed a semi-circle with Private White and loaded muskets yelling at the crowd to stop. The crowd would not stop and taunted the soldiers, telling them to fire on them. They would spit, and throw snowballs, and small objects at them.

At this point, it is very chaotic and Captain Thomas Preston never gave the order to fire, but Private Montgomery shot. The other soldiers fired as well. After, there was a pause from a few seconds up to a couple of minutes to see the aftermath of what happened.

The Aftermath

Three colonists died instantly from the volley. A rope maker named Samuel Gray, a mariner named James Caldwell, and Crispus Attucks all fell victim. Samuel Maverick, a 17-year-old was struck in the back by a musket ball and passed away the next morning. An Irish immigrant named Patrick Carr was shot in the abdomen and passed away two weeks later from the injury.

These men are all buried in Granary Burial Ground next to Samuel Adams.

This event is one of the most important ones in American history. It was an ember that would ignite a fire in the colonists that would in The Revolutionary War.

Continue to follow the brick Freedom Trail to…

11. Faneuil Hall

Faneuil Hall is a marketplace and meeting hall that has served for more than 280 years. The Hall was completed in 1742 in the style of an English country market. A fire destroyed the hall in 1761 leaving just the brick walls, and it was rebuilt in 1762.

In 1764, Colonialists first protested against the Sugar Act and Stamp Act that the British crown set up at Faneuil Hall. They set up the doctrine of the famous saying, “taxation without representation”.

The Sons of Liberty would use Faneuil Hall to publicly proclaim their dissent against the British Monarchy. At this location, they would gather to protest against the Townshend Act, the occupation of the British troops in 1768, and the Tea Act.

One of the most distinguishing features of Faneuil Hall is the golden grasshopper weather vane. Tradition says that it was used to spot spies during the War of 1812. People would ask, “What is on top of Faneuil Hall?”, and if someone answered wrong, they would know who was not from there.

Fanueil Hall is now used as a marketplace with lots of shops and plenty of places to get food. The area is one of the most visited spots in The United States.

Continue to follow the brick Freedom Trail to…

12. Paul Revere House

The Paul Revere House was built in 1680 as a three-story house. This house was first owned by Robert Howard, who was a wealthy slave merchant.

Paul Revere purchased and owned the house from 1770 to 1800. During the time of his ownership, it is believed that he added the rear chimney and the kitchen. Those are improvements that you see today in the house.

After Paul Revere sold the house, it became a building for shops and was used for a variety of different businesses. Some of these businesses include a candy store, a cigar factory, and a bank.

In 1902, Paul Revere’s great-grandson, John P. Reynolds Jr. purchased the home and took guidance in restoring it. It was preserved back to its appearance around 1700. The great thing is that 90% of the structure is original from 1680. These structures include 2 doors, three window frames, and flooring among others.

This location includes a 3,500-square-foot visitor and education center that is connected to the house. This education center was added in 2016 by the Paul Revere Memorial Association.

Continue to follow the brick Freedom Trail but first let us stop and get some food from all the walking.

Stop for a quick bite

Since you are in the North End, there are a couple of great places to stop at to get a quick bite to eat. There are a couple of staples that you have to get while you are here. These two places were highly recommended to me, and they did not disappoint at all.

First, a few blocks away is Regina Pizzeria, a local staple product of Boston. The place is also known as Pizzeria Regina and was founded in 1926 in Boston’s North End neighborhood. This is one of the best pizzas I have ever had.

Head back towards Paul Revere’s House, and you will get to the next stop for some food.

No trip to Boston would be fulfilled until you have a cannoli. Mike’s Pastry is the place to go. This is a perfect dessert to have right after the pizza. Everything is so fresh and delicious at Mike’s Pastry.

Now that we have some energy, time to continue on the brick Freedom Trail.

13. Old North Church

One if by land, two if by sea”. Every American has heard this phrase before. One of the most famous lines from the American Revolutionary War. Welcome to the Old North Church, the stop where this moment in history happened that triggered Paul Revere’s Midnight ride.

The Old North Church was built in 1723 and was inspired by the works of Christopher Wren. He was the man who was responsible for rebuilding London after the Great Fire of 1666.

This church gained its fame on the night of April 18, 1775. Three different Boston patriots were told to hang the lanterns in the church by Paul Revere. The man who hung the lanterns to make this happen was Robert Newman. These lanterns were to be used as a warning to Charlestown patriots that are across the Charles River just north of Boston.

Paul Revere and William Dawes would deliver the same message on horseback as they made their way to Lexington. They alerted patriots along with the way to be prepared. The militia was prepared because of the men and the lanterns and the battle took place on the next day, April 19, 1775.

Make sure when visiting and touring the Old North Church to check out the crypt where over 1,100 bodies are laid to rest. You will learn about the early practice of burial from the first colonists in the area and the church.

Continue to follow the brick Freedom Trail to…

14. Copp’s Hill Burying Ground

Copp’s Hill Burying Ground was founded in 1659 and is the second-oldest burial ground in Boston. The burial grounds contain more than 1,200 graves that are marked.

Some of the more well-known people that are buried in Copp’s Hill Burying Ground are Cotton and Increase Mather. They are notorious ministers that are connected with the Salem Witch Trials.

Another important figure that is buried here is, Robert Newman. He is the man that hung the lanterns on the famous night of the Midnight Ride by Paul Revere and William Dawes.

Many others are buried on the grounds. Take the tour around the grounds and discover who else is buried.

Continue to follow the brick Freedom Trail to…

15. U.S.S. Constitution

The U.S.S. Constitution is a three-masted heavy frigate of the United States Navy and was launched in 1797. She is made out of wood and is the world’s oldest ship that is still afloat. Because of the Naval Act of 1794, the U.S.S. Constitution and 5 other frigates were authorized to be constructed.

The ship was built in the North End of Boston at Edmund Hartt’s shipyard. Her first duties put her in a protective role for American merchant ships. This was done during the Quasi-War with France and to battle the Barbary pirates in the First Barbary War.

It was the War of 1812 that gave the U.S.S. Constitution the most impact. During the war, she defeated 5 British warships. It was during the battle with the HMS Guerriere that she earned her nickname of “Old Ironsides”.

After the war, she served as a flagship in the Mediterranean and circumnavigated the globe in the 1840s. The U.S.S. Constitution was retired from service in 1881 and was made a museum in 1907.

In 1997, the U.S.S. Constitution was able to sail under her power for her 200th birthday.

You can tour the ship while it sits in the harbor as it is a museum.

Continue to follow the brick Freedom Trail to…

16. Bunker Hill Monument

“Don’t fire until you see the whites of their eyes!” It is the famous line from the first major battle of the Revolutionary War. The Battle of Bunker Hill was the battle that showed that the Colonies could stand up to the British.

The Continental Army built a redoubt, a small defense fortification, on Breed’s Hill before the British could fortify the area. There was a force of 3,000 British soldiers that attacked the area with only about 1,500 colonists to hold them.

It took the British three waves to finally take the hill and defeat the Continental Army in this battle. But, it showed the people of the colonies that they were able to stand up to the British and fight against them. After the battle, about 450 colonists were killed or wounded whereas the British suffered about 1,150 in those categories.

There is confusion on the name of which hill the battle was actually fought on. The name has appeared on both hills from maps from the Continental Army and the British Army. But, the name has stuck and will forever be known as the Battle of Bunker Hill.

There is a 221-foot granite obelisk that is erected at the site of the major battle. This obelisk is the Bunker Hill Monument. The Bunker Hill Museum is across the street from the monument.

As you can see, the Freedom Trail is a major part of Boston. That is why it has to be a part of this 2 day Boston itinerary. This now concludes the Freedom Trail.

Time for a sit-down dinner and a few drinks

After all that walking, it is time to jump on the subway system. Find your proper line to get back to your hotel. Shower, clean up, and take moment to rest your feet. It will be a good time to head downtown for dinner and a few drinks.

We are going to head downtown by the TD Garden. The best way to get there is by taking the subway and getting off at North Station. There are a lot of great restaurants to pick from while you are in this area. Enjoy your meal with what you pick in downtown Boston.

After you are finished eating, it is time to grab a few drinks before heading back to the hotel. There are plenty of bars to choose from while in this area. I suggest checking out The Harp and The Greatest Bar. Both locations are fun with plenty of drink options.

It is time to head back to your hotel for the night. Make sure you check on the time for when the latest subway trains are running. The way you can get back to your hotel that way. Otherwise, you will have to use a rideshare option.

Day 2: 2 Day Boston Itinerary

Once you get up and get some breakfast, you will want to head out. Jump on the “T” and take the correct line to South Station. That will be the best place to start your day and make the short walk to the Boston Tea Party Ships and Museum.

2 Day Boston Itinerary: Boston Tea Party Ships and Museum

This is a great museum that they have put together. The Boston Tea Party Ships and Museum walks you through one of the most significant events in American history. With full re-enactments of the Boston Tea Party, you get to live the event and even get to throw tea into the harbor.

There are 8 different sections to the museum including Griffin’s Wharf, where the event took place. You will get a tour of a replica of one of the ships from that night, the Beaver or the Eleanor. Make sure to see the Robinson Tea Chest, one of the original tea chests from the Dumping of the Tea.

Take your time to walk around the gift shop and everywhere else to soak up all the history here. There are so many things to see at this location. Besides what we have mentioned, there is a theater, full re-enactments, and a tearoom to have some tea.

The Setup

On November 28th, 1773, the Dartmouth, a tea ship, arrived in Boston, the first of three tea ships to dock in Boston with tea. With the arrival of the Dartmouth, British law required that the ship be unloaded and all duties are paid within twenty days of docking.

The next day, Samuel Adams held a large meeting at Faneuil Hall. It had to move to Old South Meeting House because thousands of people showed up. The meeting passed a resolution that urged the captain of the Dartmouth to sail back to Britain without unloading and paying the duty. There were 25 men stationed to prevent the tea from being unloaded off of the ship.

Governor Hutchinson, a staunch loyalist to the crown, refused to allow the Dartmouth to leave without paying the duty. On December 2nd, the Eleanor arrived, the second tea ship. The third, the Beaver, arrived on December 15th. December 16th was the last day for the Dartmouth to pay the duty. That evening, around 5,000 to 7,000 people gathered around the Old South Meeting House. Boston’s population at this time was around 16,000 people.

Samuel Adams received word that night from Governor Hutchinson that he was refusing to let the ships leave. With that, many say Adams gave the signal to commence with their plan. That signal was him saying, “This meeting can do nothing further to save the country.”

At this point, many patriots dressed as Mohawks or Narragansett Native Americans. They wore blankets and painted their faces with soot. This was not to try to look like Native Americans but as a symbol to the watching world. That the colonists identified as “Americans” and were no longer British.

The Destruction of the Tea

On the night of December 16th, 1773, men boarded the three ships that sat in Griffin’s Wharf that night. Between the three ships, there were 342 chests of tea. The Sons of Liberty destroyed about 92,000 pounds of tea that night which is roughly £9,659 or $1,700,000. It took the men about 3 hours to destroy all the tea.

The Sons of Liberty were very precise about what got destroyed on the ships. Tea only. There was no recorded damage to any of the ships nor anything looted from them. Before they left, they even swept the deck and put things back in their proper places. They were very prideful that they only destroyed the tea and nothing else.

Somewhere between 100 and 200 Sons of Liberty participated in the destruction of the tea. The event was known as “The Destruction of the Tea” until 1834 when the term, “The Boston Tea Party” appeared in print.

Now it is time to head back to South Station and jump on the Red Line. Take that to the Park St. stop and jump on the Green Line to Kenmore. Once there, head to Fenway Park.

2 Day Boston Itinerary: Fenway Park

Being in Boston, you have to take a tour of the famous Fenway Park. Anyone who is a sports fan will enjoy the hour-long tour in one of the most famous stadiums in the world.

Fenway Park has been the home to the Boston Red Sox since 1912. The park is located in the Fenway-Kenmore neighborhood and is the oldest active baseball park in Major League Baseball. Fenway Park is also the 4th smallest park in the league based on seating capacity.

The Red Sox broke and owns the record for most consecutive sellouts in Major League Baseball. This was done with 794 regular season games and 26 post-season games. This record ran from May 15th, 2003 and to April 11th, 2013.

The Boston Red Sox has one of the deepest traditions in American sports and the stadium holds many of those traditions for the team. While taking the tour, you will get to see some of the iconic parts of the park. Stand on top of the Green Monster, see The Lone Red Seat, and learn about Williamsburg.

A fun part of the Green Monster is that the scoreboard is still updated by hand during the games. Also, seats on top of the Green Monster are some of the most expensive seats to buy at Fenway Park.

Fenway Park has been used for more than just baseball in its history. Currently, the stadium has hosted boxing, hockey, football, concerts, and many more events.

Bite to Eat

After all the walking from the Boston Tea Party and Fenway Park, it is time to grab a bite to eat. Luckily, there is a great place right next to Fenway Park.

Cask ‘n Flagon is the place to go. This is a great sports bar with plenty of seating and TVs. The menu is loaded with great food, and they have a great beer list with lots of great beer on tap.

It is easy to imagine how amazing this place has to be during a Red Sox game day.

Now it is time to head out to get one more attraction in for this 2 day Boston itinerary. Head back to the Kenmore stop on the Green Line and take that to Government Center. Once there, get on the Blue Line and get off at the Aquarium stop. From there, it is a short walk to the New England Aquarium.

2 Day Boston Itinerary: New England Aquarium

The New England Aquarium sits along the waterfront in downtown Boston. New England Aquarium area includes the main building, the Simmons Theatre, and the New England Aquarium Whale Watch. The Whale Watch only operates between the months of April and November.

This aquarium is home to thousands of aquatic animals with over 14 different exhibits to view. One of the most popular exhibits is the Penguin Exhibit. They have more than 60 penguins which are two different species, the African Penguin and the Rockhoppers.

There are a couple of touch tanks for you to enjoy. One tank is the Edge of the Sea Touch Tank. This will get you up and personal with sea stars, snails, mussels, and sea urchins. The other touch tank is the Shark and Ray Touch Tank. Here you will get close encounters with Cownose Rays, Atlantic Rays, and Epaulette Sharks.

Take time to enjoy the Giant Ocean Tank which is home to many different animals. The Giant Ocean Tank is home to a Caribbean coral reef exhibit. It hosts many reef fishes, loggerhead sea turtles, barracuda, and many moray eels. The famous resident of the Giant Ocean Tank is Myrtle, a Green Sea Turtle. Myrtle has lived in the aquarium since June of 1970.

Usually, the New England Aquarium should take you about 2 hours to complete. I would give a little more time to fully enjoy every exhibit.

Free Evening

After exploring Boston for two days on this 2 day Boston itinerary, you have deserved a night out for yourself. I have always liked to ask locals what they like and where to go. You can almost always find a hidden gem in any city this way.

So head back to your hotel by way of the “T”, get ready, and enjoy your last night in Boston.

Enjoy your trip back to the airport taking in all the great memories of Boston and how great of a city it is.

Bonus Day : 3 Day Boston Itinerary

If you are looking to extend your Boston trip for an extra day, I highly recommend that you head out of the city. Take a great trip north to the town of Salem. Salem is just north of Boston on the coast. It is most famous for the Witch Trails in 1692 and author Nathaniel Hawthorne.

Salem is a dream destination for anyone who loves Halloween and those who love the movie “Hocus Pocus”. This is kind of a Mecca for Halloween. You will probably see many people in costumes walking around if you visit in October.

The Witchcraft Trials

The Salem Witch Trails took place between February 1692 and May 1693. They were a series of hearings and prosecutions of many people accused of witchcraft. There were more than 200 people accused of witchcraft, of which 30 were found guilty, and 20 were executed.

The majority of the people found guilty and executed were women. Most of the accused were young teenage girls and even a 4-year-old. It was the deadliest witch hunt in colonial North America. It was all from mass hysteria of strong Puritan beliefs.

Of the 20 people who were executed, 14 women and 5 men were hung and 1 man was pressed to death.

Though they were all wrongly accused, this event is still one of the most famous trials in American and Colonial history.

Things to do in Salem

Take a Salem History Walking Tour. The History and Hauntings of Salem Guided Walking Tour is a great option. This is a 2 to 2-and-a-half-hour tour that will take you through a 400-year history. I recommend taking this tour at night for an experience that is more fun.

Check out the Salem Witch House. This place is a great place to get a historic look at the witch trials. The house was once owned by Jonathan Corwin, who was a judge in the witch trials.

Visit the Salem Witch Museum. This is a staple to do while in Salem. This starts you out with a 20-minute theatre presentation followed by an in-depth walkthrough of the museum.

You will also find plenty of places to eat throughout the town. Salem is a great town that has accepted its past and embraced it with pride. It is easy to spend an entire afternoon or full day in the town of Salem.

Are 2 Days Enough in Boston?

2 days are a good measuring time frame for your stay in Boston. Though, I would recommend trying to stay 3 days so that you don’t feel rushed to get everything done. But, for this 2 day Boston itinerary, you will be able to get a full Boston experience.

I recommend getting up early and being prepared to go to bed somewhat late to get everything in and not feel rushed. There will be a lot that you want to see and do in Boston. But, if you do this 2 day Boston itinerary, you will be able to get all of this in.

Is Boston Walkable?

In one word, yes. Boston is a very walkable city. The city is not way too large, but it is spread out. Luckily, with the “T”, you can take that to many different parts of the city and walk around. By combining these two, you will make able to finish this 2 day Boston itinerary fairly easily.

With the Freedom Trail, you will be able to walk some of the most important parts and not even realize how much you covered.

I enjoyed walking around the city and seeing everything. Boston is beautiful and is a city you want to take your time in to see as much as possible. Walking is the best for this.

How To Get Around Boston

Boston gives you a lot of options to get around. The public transportation makes it really easy to accomplish this 2 day Boston itinerary. Here are a few options for you.

Walking

Walking is the best way to get around Boston. As I mentioned above, Boston is a great walking city.

Boston Duck Tours

Don’t feel like walking to see all the great things that Boston has to offer? Go ahead and hop on one of the Boston Duck Tours. Is it a boat? Is it a car? Maybe both. These are a great and fun way to see Boston.

The “T” on the MBTA

Boston has a great subway system called the “T”. There are 4 main lines, orange, red, green, and blue. You can get to just about anywhere in the city this way. You can buy passes for multi-day, multi-trip, and single trips. I was able to get 4 trips for about $10. Besides walking, this was my favorite way to get around Boston.

Rideshare

Like most cities across the world, there are rideshare options to get from point A to point B. There are plenty of drivers that will be able to get you where you need to go.

Bike Rentals

Boston has a great bike rental city. You will find bikes all over the city ready to be rented out. Bluebikes is Boston’s public bike-sharing program. There are over 3,500 bikes all over the city at over 330 bike stations. You can buy passes for the bikes via an app that you download.

When To Visit Boston

The fun part with Boston, like most northern cities, it experiences all four seasons throughout the year. Seeing Boston in different seasons will make your 2 day Boston itinerary fun and interesting.

The most popular time in Boston to visit is between the months of May and October. Spring and Fall are the best times because the weather is the best. It is not too hot with all the walking that you will be doing.

Boston in the summer is warm but can be a lot of fun, especially if you are catching a Red Sox game. Baseball and summer are a perfect combination. Plus, if you are visiting in July, what better place to be for the 4th of July than where it all started?

Where To Stay In Boston

Boston has so many great spots to it. You are going to want to stay downtown area so that you are in the middle of everything. Staying downtown will make it easier to accomplish this 2 day Boston itinerary. This will make walking to locations easier.

• Revere Hotel Boston Common

This is a great hotel close to Boston Common. It is a boutique hotel located in the heart of where you want to be. You are close to subway access. The hotel features a rooftop terrace, breakfast buffet, and amazing local art.

If you are looking to save a little bit of money and stay out of the downtown area, this is a great option.

• Courtyard Boston – South Boston

This is a great hotel that is located about 3 blocks from the subway and is an easy walk to get there. The hotel is close to shopping and restaurants, including a Wahlburgers, 224 Boston, and an Olive Garden. This is a perfect option if you are looking to travel on a budget in Boston.

2 Day Boston Itinerary: In Conclusion

Boston is a beautiful city and I look forward to visiting it again. I feel like this 2 day Boston itinerary will give you a full experience in Boston without missing the major parts. Of course, I can’t fit everything into 2 days, but I tried to find the most Boston things for everyone.

I hope that you enjoyed this 2 day Boston itinerary and will use it to make your Boston trip the best experience for you.

Take your time to enjoy the city and see the things you want to see. Eat some Chowdah and learn the “T” so you can be Wicket Smaht.

If you have enjoyed learning about the Revolutionary War from Boston, check out a few of my other posts that involve the Revolutionary War from Charleston, South Carolina.

• 11 Best Historic Sites in Charleston South Carolina
• What 13 things should I not miss in Charleston SC
• 7 Best Plantations in Charleston to visit
• Why is Charleston called the Holy City

• Make sure you book your flights
  • Find a great flight at a great price through Booking.com They have many options for Flights, Cars, Hotels, and more! Make sure to book your trip today!
• Pick up your travel items
  • Head over to Amazon.com to get your needed travel items. Pick up the travel backpack that I use for my travels or my post about what to bring for a day hike. Take a look at the items to bring along in a 2-3 day backpacking trip with my post What To Pack In Your Hiking Backpack. Use this or pick up more items that you will need.
• Helping The Traveling Drifter
  • By purchasing from the provided links, a small commission is earned to help keep the website running. I thank you for your support and for following the website.