New England is such a special part of the US, and the city you have to explore when visiting this region is Boston. With tons of historic charm, amazing food, and museums galore, Boston is one US city you really can’t miss. This 3 day Boston itinerary will help you dip your toes into some of the best the city has to offer.
Boston is the city that inspired me to move to the East Coast. I did a studies program there in college and never left the East Coast. I vowed to make it my home after college, and it has changed my life, so this itinerary and city hold a special place in my heart!
Table of Contents
3 Day Boston Itinerary Overview
- Day 1: Explore historic Boston (Freedom Trail, Faneuil Hall, Quincy Market, choose historic ship tour, North End)
- Day 2: Get to know neighborhoods and gardens (Beacon Hill, Public Gardens, get on the water, dinner in Seaport)
- Day 3: Learn at museums and enjoy sports (Choose a museum, explore on Newbury Street, Boston Public Library, watch sports)
Flight Cost: $100 – $200 (from DC)
Average Hotel Cost: $200 a night
Tips for Visiting Boston
Before we get into the itinerary, here are a few tips for visiting Boston that will help you make the most of your trip!
Getting Around
Boston is a very walkable city. It’s not too big, and most of the things you’re going to do are within walking distance of each other on this itinerary, and in general, the tourist attractions are in a reasonably small area.
Boston also has excellent public transportation, with the T (subway) system that is easy to navigate. There’s also a large commuter rail system through the T, making it easy to take day trips if you’d like. You can also get from the airport into Boston easily on the T. Here’s a map for reference.
Traffic in Boston can get pretty bad, and New England drivers are not known as the most friendly. When I first came to Boston from Texas, it was a big culture shock for me, the way people aggressively drive!
Unless you plan on doing a road trip from Boston, I’d recommend relying on public transit or taking a quick Lyft/Uber if you need to. New to Lyft? Here’s 50% off your first ride!
Best Time of Year to Visit
While New England is a year-round destination, I highly recommend visiting Boston in particular in the summer or fall. The weather in summer is in the 70s and 80s (Fahrenheit), which is amazing, but it can get humid. In the fall, you can expect vibrant red, orange, and yellow leaves on the trees, making the historic streets even more charming!
No matter the time of year, you should plan to bring layers. In summer, bring a light sweater; even a pair of jeans won’t be a bad idea to pack for evenings. In the fall, you may need a winter coat, as it can get chilly.
When visiting in winter or early spring, plan on bringing a warm coat and waterproof shoes. Nothing is worse than rain soaking through your shoes when it’s like 40 degrees out.
Local Etiquette
There’s this misnomer that New Englanders are rude. In reality, I find them to be some of the nicest people, but they are more direct. Don’t take it personally, and go with the flow! People won’t open doors for you; they probably won’t help unless you ask, and there’s less small talk.
Other Tips to Know
- Touristy areas are packed with street performers. They will try to lure people in for a long time before actually giving a small performance. I would walk past and keep moving!
- Bring a reusable water bottle – plenty of places for water in Boston and plenty of public restrooms in touristy areas, especially along the Freedom Trail.
- Always look around, you never know when you’re passing a historic spot – you’ll find plaques and architecture everywhere. You’ll walk past a steak house that was the first public school, or a Chipotle that was the birthplace of a Founding Father.
Where to Stay in Boston
- Most convenient and the easiest to get to main sites? Obviously, it’s downtown, but downtown is really expensive, so keep that in mind! That said, for a nice option, consider the Hilton Park Plaza Hotel, or for a splurge, XV Beacon.
- Easy to get into downtown on the T – I’d recommend Cambridge! There are lots of options just on the other side of the river, like the Royal Sonesta Cambridge, which has amazing views and is right near the T for easy public transit.
Day 1: Explore Historic Boston
Boston is full of history, and to get to know the city, spend the first day exploring some of the most important historic sites related to the founding of the United States!
The things on this itinerary can be done in any order. Still, I do recommend them in the order on this day in particular because the first one will give you context for everything else on the itinerary for the 3 days in Boston.
Morning: Walk the Freedom Trail
On your first day in Boston, you have to start with the thing that everyone talks about – The Freedom Trail. The Freedom Trail is a 2.5 mile long walk through downtown historic Boston that takes you to 16 sites that were integral to the American Revolution.
Sites include museums, burial grounds, cemeteries, and historic buildings. Many of these you can either pay to visit or walk through quickly. Some are quick stops, others you could spend an hour at. It’s completely up to you how much or how little you can do.
There are tour options, but honestly, you can do this entirely on your own, too. Either way, you likely start at the Boston Common Visitor Center. The Visitor Center has free (and paid) map options if you’d like to walk it by yourself, but most tours also start here, too.
Not everything on the Freedom Trail is a long stop, and I recommend reviewing the list of activities ahead of time so you can decide which museums to visit and which to pass by. Here are all the sites on the Freedom Trail.
Some highlights include:
- Massachusetts State House
- Old South Meeting House (where the Boston Tea Party Began)
- Boston Massacre Site
- Paul Revere House
- USS Consistution
Lunch at Fanueil Hall and Quincy Market
After all the walking, you’re going to be hungry, and why not combine a historic spot with some food and shopping?
If you choose to walk this on your own, I recommend stopping at Faneuil Hall and Quincy Market for lunch to break things up, or even to end your walk along the trail!
Faneuil Hall is a historic market that first opened in 1742, featuring stalls and vendors operated by Peter Faneuil. Faneuil Hall is known as the “Cradle of Liberty” for its role in Revolutionary protests and speeches by figures such as Samuel Adams. Today, it hosts a variety of shops (most are very touristy and expensive), and the building itself is partially a museum.
After a walk-through, head next door to Quincy Market for food and more shopping. While touristy, this area is a must in my mind! You’ll find several great food spots perfect for quick, easy bites of Boston’s signature dishes, like clam chowder and lobster rolls.
On my latest trip to Boston, I ate four lobster rolls (two of which were in Maine), and Quincy Market actually had my favorite lobster roll of the trip, so don’t discount the food here! Go to Boston & Maine Fish Co for some great lobster rolls in Quincy Market.
There’s also the Sam Adams Tap House here, which makes for a fun stop for a drink. There’s a rooftop that is great to hang out on while relaxing on a sunny day!
Afternoon: Choose a Historic Ship to Tour
After some food and shopping, it’s time for one more piece of US history! Choose to continue the Freedom Trail, ending at the USS Constitution, or head over to the Boston Tea Party Ship and Museum. Below are the details for both, so you can decide which is more interesting to you.
Option 1: Continue the Freedom Trail and Tour the USS Constitution
Faneuil Hall is not the end of the Freedom Trail; you can continue it on through the northern part of Boston to see Paul Revere’s house, Old North Church, and Bunker Hill. It ends at the USS Constitution as the last stop, where you can explore American naval history.
The USS Constitution was never defeated in battle, and the museum provides an immersive experience that highlights the legacy of “Old Ironsides.” It is technically still part of the US military, and the world’s oldest commissioned naval vessel still afloat.
The ship is free to visit on a first-come, first-served basis, but does have a suggested donation. The USS Constitution is an active-duty ship operated by the US Navy, and there are additional security requirements, including screening and presenting ID to board the ship.
Option 2: Boston Tea Party Museum and Ship
Your second option for the afternoon is to visit the interactive Boston Tea Party Museum and Ship. This museum requires scheduling a time to join a guided tour of a reenactment of the Boston Tea Party.
You’ll be led through a historic re-enactment of how the Boston Tea Party began. Everyone gets a character and is part of the fun. After the re-enactment, you board the ship where you can throw tea into the Boston Harbour and learn more about the American Revolution.
Once the tour ends, you can head to the tea room to sample American Revolution-era teas and snacks. You can also arrive early or visit the tea room only if you don’t want to take a tour.
Evening in North End (Little Italy)
After history and walking around for the day, what better way to end your day than loading up on some delicious carbs, aka pasta and pastries, in Little Italy!
Little Italy is in Boston’s historic North End and is a lively neighborhood known for Italian-American culture.
If you choose to walk the entire Freedom Trail in the afternoon and are already in the area, it makes for a great final stop for your day! If you choose not to do this part of the Freedom Trail, you can still see Paul Revere’s House and other sites when you head here for your evening. Just arrive earlier (or stay later) if you want!
This neighborhood is full of charm, with cobblestone streets, and is very walkable. You’ll find tons of restaurant options, and I’d highly recommend making a reservation in advance if you can. Places get busy, and there are often festivals and special events in this area, making it even busier.
Popular spots like Mike’s Pastry can have really long lines; don’t be afraid to head somewhere else, like Bova’s or Modern, for a cannoli instead. Look for a small Italian spot on a side street if bigger places are all full. There are plenty of options!
I will not recommend the most recently place I ate – we had a reservation and were still waiting an hour and a half past our reservation time… be warned if there’s an event in Little Italy – go on a different day!
Day 2: Neighborhoods and Gardens
After a day of exploring Boston’s history, on your second day, get to know the city’s best neighborhoods and gardens that bring the city so much charm. When I lived in Boston, I loved just roaming some of the most beautiful areas with cobblestone streets and historic charm.
You can walk around all day, just looking for plaques that tell you about different historical places and markers. I like to keep my phone on hand while walking around (with a portable charger) so I can Google more details as I see things! Below are areas I’d recommend exploring.
Morning in Beacon Hill
Start off your morning in one of my favorite Boston neighborhoods – Beacon Hill. One of Boston’s oldest neighborhoods, Beacon Hill is known for its charming, narrow cobblestone streets, federal style row houses, and gaslit streetlamps.
Start your morning at Beacon Hill Books and Cafe. You can make a reservation for breakfast here, or grab a coffee and a pastry to go, depending on how much time you have. The cafe and bookstore are both adorable, well worth spending some time at!
From there, head down Charles Street and make stops in the different shops along the way. Beacon Hill is full of cool vintage shops, boutiques, and great places to pop into.
Walk over to the famous Acorn Street to snap a few beautiful pictures, then meander down the side streets until you get to Boston Common and the Public Gardens. There’s something so fun about just exploring a gorgeous historic neighborhood on a quiet morning!
Optional: Grab a picnic-style lunch from Tatte on Charles Street to bring to the Boston Public Gardens.
Walk the Public Gardens
The Public Garden was the first public botanical garden in America. It was decorative and flowery from its inception, featuring meandering pathways for strolling. It dates back to 1839 during the Victorian Era, and you’ll find a lot of the historic charm lives on to this day!
You can walk the different paths, seeing different famous statues, beautiful bridges, and of course, plenty of flowers and greenery! In the center of the gardens, you’ll find a large pond with historic swan boats, owned and operated by the same family for over 100 years.
Use a map to walk around so you don’t miss any statues, or just meander and have your picnic lunch if you decided to bring that with you from Beacon Hill.
If you decided not to bring a picnic lunch, you can head to Parish Cafe for some great local sandwiches and bites. Each sandwich was created by a different Boston chef, which makes it extra fun to eat here.
Afternoon: Get on the Water
In the afternoon, explore the water that surrounds Boston with a boat tour, renting kayaks, or taking a stroll along the Charles Esplanade! Below, I’ll outline each option so you can choose the one that works best for you and your preferences.
Option 1: Boat Tour
Throughout Boston, you’ll find several different boat tour options to see the city from a different perspective. Spending an afternoon on a boat, relaxing and taking in the views, can be a fantastic way to see the city!
Take a classic tour on a sailboat with drinks, learn about the architecture and history of Boston, or take a booze cruise on a tiki boat to some different harbours! There’s really a cruise for everyone. Most last 1-2 hours, and you’ll want to bring a light jacket pretty much any time of year.
Option 2: Rent Kayaks or SUP
If you’re looking for something more adventurous, rent kayaks or paddleboards from Paddle Boston and explore the Charles River.
You’ll be able to take in the great views of the Boston skyline and the Charles River Esplanade, as well as other nearby landmarks like the Zakim Bridge, M.I.T., the Museum of Science, and Boston University.
This is a nine-mile stretch of river with no current, allowing for easy round trips, and is a great choose your own adventure afternoon! You can spend one hour or three hours kayaking along and taking in the views.
Reservations are not required, but they do close in the fall/winter when it gets colder, so call ahead if you aren’t sure!
Option 3: Stroll the Charles Esplanade and View Boston
Want something more relaxing but still active? You can stroll along the Charles Esplanade to take in the river views! You’ll get great views of the river, Cambridge, and even run into a few bars/rooftops along the way.
You can also rent a bike from Blue Bikes and take it along the river for a fun afternoon. The trail is flat, making it easy for beginners!
Drinks with a view, anyone? You can stop at Nighshift Esplanade for a beer garden, or at ArtBar (on the other side in Cambridge) for great views of Boston along the Charles.
End your afternoon with a stop at the View Boston Observation Deck for great views. It’s Boston’s only observation deck and offers great 360-degree views of the city from 50 floors up!
Dinner in Seaport or Back Bay
After your afternoon on the water, head to dinner in one of Boston’s newest neighborhoods – Seaport. If you’re looking for dinner with a view, this area is perfect for an evening! You’ll find plenty of options for great seafood with a view (and other food), but the draw of Boston is the fresh seafood, if we’re being honest.
Consider Row 34 or Lolita Fort Point. Dinner in this area is on the expensive side, so do be prepared for a higher bill if you choose to eat in this area! It’s good for those who may want a nice night out on their trip.
For something more affordable, head to Back Bay. This area of Boston is lined with elegant brownstones, and you’ll head here tomorrow for more exploring! Saltie Girl is a great seafood spot in this area and is more lowkey, but still nice.
Day 3: Museums & Sports
On your third day, it’s time to visit some of the museums that Boston is known for (beyond the history, of course!). Boston is a hub for learning, with some of the best known universities in the world, like Harvard and MIT, so, of course, it’s also a hub for world class museums.
New Englanders are also very passionate about their sports, and no matter which season you choose to visit, you’ll have a team to watch. A Boston sports game is a true experience!
Morning: Choose a Museum
As mentioned, you’ll have no shortage of museum options in Boston to visit! There are all types of museums in Boston, depending on what you’re most interested in. Below are a few of my favorites to choose from.
Option 1: Isabella Stuart Gardner Museum
The museum first opened in 1903 in a building modeled on a Venetian Palace from the 15th century. The building itself is beautiful, but the art is also stunning! There’s a variety of art here from all over the world, so there is something for everyone.
Each room feels unique, and you’ll love taking your time here. You’ll also notice empty frames around the museum. These are still in place after a famous art heist that happened in the early 90s. Watch “This Is a Robbery: The World’s Biggest Art Heist” on Netflix to learn more!
Option 2: Museum of Fine Arts
First opened in 1870, this museum is among the largest in the US, with over 500,000 works of art. It’s also Boston’s most visited museum. You’ll find many beautiful works of art from around the world here and enjoy strolling through the various exhibits.
Some of the most notable pieces are by artists like Van Gogh, Rembrandt, Degas, Sargent, and an Egyptian collection.
Option 3: Museum of Science
Last but not least on the list is the Museum of Science. For those who want something more hands-on or interactive, this is a great one to choose (this is a great one for kids!). The museum covers science, technology, engineering, and mathematics with over 500 exhibits.
You won’t want to miss the planetarium either (this is an extra charge, but worth it)! There are live demonstrations, workshops, and scavenger hunts to keep the whole family entertained here.
Early Afternoon: Newbury Street and Boston Public Library
After spending the morning at a museum, head over to Newbury Street for lunch and some shopping. Newbury Street is located in Back Bay and is one of the prettiest areas in the city. You’ll find large brownstones, major retailers, art galleries, and fun shops all throughout this area.
It’s very walkable, so spend some time walking from the far end of the street to downtown Boston. This would mean starting around Massachusetts Ave and heading east. Stop anywhere that catches your eye along the way.
There are plenty of lunch options around here, but a few I’d recommend would be Salty Girl for some great seafood (if you didn’t go here last night!), Eataly for great Italian food, or Eva for some great Mediterranean food.
From here, you have ot stop by the Boston Public Library. This was the first public library to lend books in the United States. It was established in 1848 and is a stunning building.
It can be a quick stop, or you can spend some time here with an afternoon tea in the library in the Courtyard Tea Room, or grab cocktails at Map Room Lounge (yes, both are actually IN the library!). Such a special and unique experience! Make sure to book in advance.
Photo by Farid Briones
Afternoon/Evening: Watch a Game
New England sports fans are truly die-hard, with some of the oldest teams in the US, making a game, no matter the sport, a fun addition to your trip. To end your trip or, honestly, whatever day the schedule works out for, add a game to your itinerary!
Here are the teams and games to choose from:
- Baseball: See the Red Sox play at the historic Fenway Ball Park (late March/early April to early October)
- Basketball: Watch the Celtics downtown at TD Garden (October/November through April/June)
- Football: Spot the Patriots at nearby Gillette Stadium (late August/early September through January)
- Hockey: Take in a Bruins game at TD Garden downtown (October to June)
- Soccer: Have fun at a New England Revolution game at Gillette Stadium (late February/early March through October)
Ideas to Extend your Trip:
- Take a coastal road trip from Boston to Portland, stopping in iconic towns along the way
- Take a day trip to Salem, Massachusetts, and learn about the history of the Salem Witch Trials
- Drive up to Vermont (especially in the fall or winter) and get incredible mountain views
- Book a tour of Harvard and spend some time at one of the most famous universities in the world
- Head out for some beach time to Cape Cod or Martha’s Vineyard
There’s no shortage of great things to do in Boston. It’s a vibrant city that feels distinct from other US cities, with a history dating back to the American Revolution and earlier.
This 3 day Boston itinerary is packed with things to give you the best of the city – I hope you absolutely love your trip to Boston and that you get to do even more exploring of New England beyond Boston too!
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