Planning your first trip to Boston? Then this 3-day Boston itinerary will be perfect for you.
Boston, often referred to as the Cradle of Liberty, is the capital of Massachusetts and one of the oldest cities in the United States.
As the birthplace of the American Revolution, Boston was the setting of several key historical events, including the Boston Tea Party, Paul Revere’s Midnight Ride and the Battle of Bunker Hill. Many of these historic sights can be visited along the Freedom Trail, one of the top things to do in Boston.
Beyond its rich history, Boston is also home to some of the world’s oldest and most prestigious universities, including Harvard and MIT, as well as some of the most successful American sports teams, such as the Boston Red Sox, New England Patriots, and Boston Celtics.
About this 3-Day Boston Itinerary
This 3-day Boston itinerary is written from the perspective of a British female solo traveller and is based on my own trip to the city.
An alternative Day 2 option is included, as whale watching is a seasonal activity. If you’re visiting during the off-season – or simply prefer to skip it – you’ll find a list of alternative activities instead.
This itinerary is ideal for solo travellers, first-time visitors to Boston, and international travellers visiting the US, particularly those with an interest in history, wildlife, day trips, and the classic tourist experience.
3-Day Boston Itinerary Overview:
- Day 1: The Freedom Trail
- Day 2: Whale Watching & New England Aquarium
- Day 2 (Alternative): Harvard Walking Tour, Boston Tea Party Ships & Museum, Fenway Park and Boston Public Library
- Day 3: Salem Day Trip from Boston
Day 1: Freedom Trail
Day 1 of this 3-day Boston itinerary is dedicated to the Freedom Trail, a 2.5 mile walking route through Boston that connects 16 historic sites relating to the American Revolution.
The trail begins at Boston Common and winds through downtown Boston, passing many of the city’s most significant historical landmarks. From there, it continues into the North End, Boston’s oldest residential neighbourhood known for its Italian American heritage.
The trail ends across the Charles River in Charlestown, concluding at the Charlestown Navy Yard, home to the USS Constitution, and the nearby Bunker Hill Monument.
A line of red bricks marks the Freedom Trail, although in some parts it’s just a painted red line.
The first part of the trail, from Boston Common to Copp’s Hill is under 2-miles and can be walked in less than an hour without stops. However, this doesn’t factor in stopping and visiting sights, therefore it is recommended to reserve the morning for the first portion of the trail.
The second part of the trail continues across the Bill Russel Bridge into Charlestown, around a 20-minute/1-mile walk from Copp’s Hill.
Stop 1: Boston Common
The Freedom Trail starts at Boston Common, a public park in downtown Boston and the oldest public city park in the US.
Boston Common has hosted numerous public celebrations and demonstrations. Martin Luther King Jr, Pope John Paul II and Sarah Palin have all spoke here.
You can visit the Boston Common Visitors Centre for more information on the Freedom Trail, tours, and other sights in Boston.
Stop 2: Massachusetts State House
Distance: 1-minute walk from Boston Common.
The Massachusetts State House was completed in 1798, it serves at the state capitol and seat of government in Massachusetts. The golden dome is one of Boston’s most iconic landmarks.
Self-guided or guided tours of the Massachusetts State House are available on weekdays year round.
Side Stop: Beacon Hill
Next to the Massachusetts State House is the upmarket neighbourhood of Beacon Hill featuring the iconic cobbled Acorn Street. Take a quick detour down Chestnut and Mount Vernon Streets.
Stop 3: Park Street Church
Distance: 4-minute walk from Massachusetts State House
Park Street Church is an Evangelical Church located in downtown Boston, dating back to 1809. A granary was located on the site in the 1700s, after construction of the Massachusetts State House, plans for a church were drawn up. The church was nicknamed Brimstone Corner, as gun powder was stored in the crypt during the war of 1812.
Stop 4: Granary Burying Ground
Distance: Next door to Park Street Church
Granary Burying Ground is the third oldest burying ground in Boston, first used in 1660. It is named after the granary that once stood on the site of the nearby Park Street Church.
There are numerous famous people buried here including Peter Faneuil, benefactor of Faneuil Hall, and Paul Revere, best known for the Midnight Ride. Samuel Adams, John Hancock, and Benjamin Franklin’s parents are also buried here.
Stop 5: King’s Chapel & King’s Chapel Burying Ground
Distance: 3-minute walk from Granary Burying Ground
King’s Chapel was founded in 1686 as an Anglican (Church of England) Church. After the American Revolution, it adopted a new theology and became the first Unitarian church in America.
The nearby King’s Chapel Burying Ground is Boston’s first and oldest burying place dating back to 1630. The chapel and the burying ground are separate sites, with the burying ground predating the church by more than 50 years.
Stop 6: Boston Latin School/Benjamin Franklin Statue
Distance: 4-minute walk from King’s Chapel
A mosaic on the pavement marks the site of the original location of Boston Latin School dating back to 1635. A statue of Benjamin Franklin, the school’s most famous student is located nearby. The Boston Latin School remains a part of the public school system, however it is now located in a different part of the city.
Stop 7: Old Corner Bookstore
Distance: 1-minute walk from Boston Latin School.
The Old Corner Bookstore is one of Boston’s oldest surviving buildings, it now houses a Chipotle. It once housed the office of Ticknor and Field’s, America’s leading publisher of books. Some of the most famous American literature was published here.
Stop 8: Old South Meeting House
Distance: 1-minute walk from Old Corner House
The Old South Meeting House is a historic church and meeting house in downtown Boston. The current house was built in 1729, replacing the earlier house built 60 years earlier.
Old South Meeting House was the largest building in Boston and used for mass meetings that lead to the Boston Tea Party, and ultimately the American Revolution.
The building is preserved as a museum. One ticket allows entry into both the Old South Meeting House and the next stop on the Freedom Trail, the Old State House.
Stop 9: Old State House
Distance: 3-minute walk from Old South Meeting House
The Old State House was built in 1713 and served as the centre of royal government in the Massachusetts Bay Colony. After the Revolution, it became the first state capitol building. The government relocated to the New State House (stop 2 on the Freedom Trail) in 1798.
The Old State House is the oldest surviving public building in Boston, and can be visited alongside the Old South Meeting House.
Stop 10: Boston Massacre Site
Distance: 1-minute walk from Old State House
The site of the Boston Massacre is marked by a cobblestone ring. The Boston Massacre is considered to be the first bloodshed of the American Revolution. On 5th March 1770, 5 Boston residents were killed when British soldiers fired into a crowd during a confrontation.
Stop 11: Faneuil Hall
Distance: 4-minute walk from Boston Massacre Site.
Faneuil Hall is a historic meeting hall and marketplace dating back to 1742. It was a gift from the wealthy merchant Peter Faneuil, who wanted to build a marketplace to encourage trade. This offer proved to be controversial, and so a meeting hall was constructed above the marketplace as well.
The Faneuil Hall Marketplace, better known as Quincy Market, is an extension built in 1826. In the central hall you will find a variety of food stalls, making it the perfect place to stop for lunch on the Freedom Trail.
The North End
The next section of the trail leads into the North End – Boston’s Little Italy. In 1930, 99% of the population of the North End were Italian immigrants, because of this you will find numerous Italian restaurants. If you didn’t stop for lunch at Quincy market, then this is the perfect place to grab a bite to eat.
Stop 12: Paul Revere House
Distance: 8-minute walk from Faneuil Hall.
The Paul Revere House is Boston’s oldest structure built in 1680. Paul Revere, American Patriot, best known for the infamous Midnight Ride, bought the house in 1770 and lived there intermittently for 30 years.
The building has been altered multiple times over the years, a third floor was added in the 18th century, this has since been removed to appear similar to its original appearance.
The house was preserved as a museum in the early 20th century and you can undertake self-guided tours of the interior.
Stop 13: Old North Church
Distance: 5-minute walk from Paul Revere House.
The Old North Church, officially known as Christ Church in Boston, is an Episcopal church located in the North End of Boston.
Old North is famous for its key role in Paul Revere’s Midnight Ride. On the night of 18 April 1775, two lanterns were displayed from the church’s steeple to warn Patriots in Charlestown about the movement of British troops. This prompted Revere to set out on his ride to alert colonial leaders that the British were marching toward Lexington and Concord.
Stop 14: Copp’s Hill Burying Ground
Distance: 2-minute walk from Old North Church.
Copp’s Hill Burying Ground is situated on the highest point of the North End. It is the second-oldest burying ground in Boston, dating back to 1660.
Copp’s Hill is named after William Copp, a shoemaker who owned the land before it was bought for burials. Unlike other burying grounds located on the Freedom Trail, it contains the graves of few famous people.
Stop 15: USS Constitution
Distance: 20-minute walk (across the Bill Russell Bridge) from Copp’s Burying Ground.
The USS Constitution is the oldest commissioned warship afloat in the world, built in Boston and launched on 21st October 1797.
Located at the Charlestown Navy Yard, you can explore onboard the ship, visit the Navy Yard Visitor Centre or the USS Constitution Museum in Building 22 to learn more about the ship.
Stop 16: Bunker Hill Monument
Distance: 10-minute walk from USS Constitution.
The Freedom Trail ends at the Bunker Hill Monument in Charlestown. The Bunker Hill Monument is a 221-foot granite obelisk built on the site of the Battle of Bunker Hill.
The Battle of Bunker Hill was fought between British forces and colonial troops during the first part of the American Revolutionary War, on 17 June 1775. Although it was a British victory, it was not without heavy losses.
Visitors can ascend the monument, or learn about the battle at the Bunker Hill Museum.
Self-Guided or Guided Freedom Trail Walking Tour
On this 3-day Boston itinerary, the Freedom Trail can be walked independently or with a guided walking tour.
You can read my in-depth Self-Guided Freedom Trail Walking Tour guide here.
The Official Freedom Trail tour leaves from the visitors centre at Boston Common. It lasts 90-minutes and covers 11 of the 16 Freedom Trail historic sites, ending at Faneuil Hall. Tours can be booked online on the Freedom Trail Website.
Day 2: Whale Watching & New England Aquarium
On day 2 of this 3-day Boston itinerary, spend the morning on a whale watching cruise. In the afternoon, continue the marine life theme with a visit to the New England Aquarium.
Whale-Watching Cruise
Between May and October, you can take a whale watching boat tour from Boston Harbour to see whales in their natural habitat.
The New England Aquarium Whale Watch Cruise includes a naturalist giving commentary on wildlife. Wildlife to look out for include humpback, fin and minke whales, as well as porpoises and seals.
Whale watching cruises can be booked on the Boston City Cruises website. Tours last 3-4 hours and depart from 1 Long Wharf, Boston, MA.
The 2026 whale watching season begins on 16 May 2026 and ends on 1 Nov 2026. Prices start at 75 USD for adults, with reduced prices for seniors (65+) and children.
I did the New England Aquarium Whale Watch Cruise in October, and was fortunate enough to see several humpback whales. As I only used my iPhone for photos, I don’t have very good images, however I thoroughly enjoyed the experience.
My number one tip when doing a whale-watching cruise during your 3-day Boston itinerary is to take motion sickness medication. If you suffer from moderate to severe motion sickness, I would completely avoid, or try to go when the swells are low.
During my trip, numerous adults and children were sick and there was vomit everywhere (an emetophobe’s nightmare)! There were a lot of people who could not enjoy the trip whatsoever as they were either vomiting themselves or caring for other people.
New England Aquarium
Opening Times: Mon – Fri – 09:00 – 17:00, Sat & Sun – 09:00 – 18:00
Location: 1 Central Wharf, Boston, MA 02110
Admission Fee (Aquarium + Movie): Adult – 39 USD, Child (3-11) – 30 USD, Children 2 and under – free, Seniors (60+) – 37 USD. (Aquarium only): Adult – 34 USD, Child (3-11) – 25 USD, Children 2 and under – free, Seniors (60+) – 32 USD.
The New England Aquarium is located next to the departure point for whale watching cruises. After your tour, visit the New England Aquarium, which is the perfect way to finish a marine-centred day.
Animals you can see include African penguin, Atlantic harbour seal, California sea lion, giant Pacific octopus, green sea turtle, and southern rockhopper penguin. There are also thousands of saltwater and freshwater fish.
The Giant Ocean Tank spans four floors and features a Caribbean coral reef exhibit. Daily feeding dives take place at 10:00 and 14:00.
You can also watch a movie in the Simons Theatre. Movies shown include Call of the Dolphins 3D, Shark Kingdom, and Secrets of the Sea. All films last 45-minutes, and showing times can be checked on the New England Aquarium website.
Day 2 (Alternative): Harvard Walking Tour, Boston Tea Party Ships & Museum, Fenway Park and Boston Public Library
If you’re visiting Boston outside of whale-watching season, you suffer from motion sickness, or you simply don’t fancy going on a whale-watching cruise, then here is an alternative day 2 of this 3-day Boston itinerary.
Harvard Walking Tour
Take a walking tour of Harvard, one of the world’s oldest and most prestigious universities.
The Harvard University student-guided walking tour also known as the Hahvahd Tour lasts around 70-minutes.
You will learn about the USA’s oldest university and see some of its most notable landmarks including Memorial Hall, Widener Library, the Johnston Gate and the John Harvard Statue. Tours are led by a student giving an insight into life at the university.
Tours start outside the Main Harvard Redline Subway Station in the middle of Harvard Square.
You can reach the Main Harvard Redline Subway Station from downtown Boston by rail. From South Station, Downtown Crossing or Park Street, take the Red Line in the direction of Alewife to Harvard Station. Journey time is between 10 and 15 minutes depending on departure station.
You can book the Hahvahd Walking Tour on the Trademark Tours website, Viator or Get Your Guide.
Boston Tea Party Ships & Museum
Location: 306 Congress Street, Boston, MA 02210
Opening Hours (In Season): First tour 10:00, last tour 17:00, Abigail’s Tea Room – 09:30 – 17:00.
Opening Hours(Off Season [1 Nov 25 – 31 Mar 26): first tour 10:00, last tour 16:00, Abigail’s Tea Room – 09:30 – 18:00.
Admissions Fee: Adult – 36 USD, Children (3-12 years) – 26 USD, Children (2 and under) – free.
At the Boston Tea Party Ships & Museum you can learn about the event that became a key moment leading to the American Revolutionary War. You can walk aboard recreations of the ships the Beaver and the Eleanor, visit the museum, see the Robinson Tea Chest (the only known surviving tea chest from the Boston Tea Party), and have a cup of tea in Abigail’s Tea Room.
On 16 December 1773, American colonists boarded British ships and dumped 342 chests of tea into the water in protest of the Tea Act, which allowed Britain to tax tea sold in the colonies.
Boston Public Library
Location: 700 Boylston Street, Boston, MA 02116
Opening Times: Mon – Thu – 09:00 – 20:00, Fri & Sat – 09:00 – 17:00, Sun – 11:00 – 17:00
Admission: Free
The Boston Public Library was first established in 1848. It was the first public library to lend books, first to have a branch library, and the first to have a children’s room.
Boston Public Library consists of the central library and 25 neighbourhood branches. The central library has two buildings: the McKim building opened in 1895 and the Boyston Street building from 1972.
A visit to the historic McKim building is a worthy inclusion of any 3-day Boston itinerary.
Fenway Park
Location: 4 Jersey Street, Boston, MA 02215
Fenway Park, often referred to as America’s Most Beloved Ballpark has been home to the Boston Red Sox since 1912.
Tours of Fenway Park are available year-round. You can find tour options, availability, and prices on the Major League Baseball (MLB) website.
Day 3: Salem Day Trip from Boston
On the last day of this 3-day Boston itinerary, take a day trip to Salem.
Salem, also known as the Witch City, is a coastal town in Massachusetts best known for the Salem Witch Trials of 1692 and only 25 miles from Boston.
The Witch Trials have had a lasting effect on Salem as well impacting popular culture. The 1993 cult-classic Hocus Pocus was not only set in Salem but filmed there too.
Salem is considered to be one of the top Halloween destinations in the US, welcoming over a million visitors during the month of October. Despite this, it makes for a great day trip Boston all year round.
You can read my in-depth Salem Day Trip from Boston (+Hocus Pocus Filming Locations) here.
How to Get to Salem From Boston?
You can take the Newbury/Rockport Line from Boston North Station to Salem Station, the journey takes 35-minutes (5-stops).
Between May and November, you can take the ferry from Long Wharf in Boston to Salem, the journey is around 50-minutes. Although more expensive, it is considerably more scenic and atmospheric.
The drive time to Salem from Boston is around 45-60 minutes depending on traffic. Parking can be very difficult to find when visiting in high season.
Things to Do in Salem
The Witch House at Salem
Location: 310 1/2 Essex St, Salem, MA
The Witch House is one of the few buildings in Salem with direct links to the Salem Witch Trials.
Salem Witch Museum
Location: 19 1/2 Washington Square North, Salem, MA
Museum dedicated to the 1692 Salem Witch Trials.
Salem Witch Trials Memorial
Location: 24 Liberty St, Salem, MA
Memorial to the 20 people executed during the 1692 Salem Witch Trials.
Bewitched Statue
Location: 237 – 245 Essex St, Salem, MA
Statue of Samantha Stephens from the 1960s TV show Bewitched.
Old Burying Point Cemetery
Location: 51 Charter St, Salem, MA
The oldest cemetery in Salem dating back to 1637.
The House of the Seven Gables
Location: 115 Derby St, Salem, MA
17th century colonial mansion which served as the inspiration for Nathaniel Hawthorne’s novel the House of the Seven Gables.
Peabody Essex Museum
Location: 161 Essex St, Salem, MA
Art and History museum with one of the major collections of Asian art in the US.
Salem Maritime National Historic Site
Location: Across Salem
12 historic structures along the Salem waterfront relating to Salem’s maritime past in trading in the 18th and 19th centuries.
Final Thoughts on 3-Day Boston Itinerary
This 3-day Boston itinerary is a great introduction to this interesting New England city.
Whether you’re visiting Boston’s historical sights, going on a whale watching cruise, or enjoying Boston’s food and sports culture, there is something for everyone.
I hope you enjoy your trip to Boston!