With a mix of history, city life, and delicious eats, Boston is a must-visit city in the United States. In this guide we’re sharing how to spend 2 days in Boston, including an itinerary, tips for visiting, where to stay, and more!
For years we have dreamt of wandering around the Freedom Trail, eating some chowda, and watching the Red Sox in Boston. We finally made it happen and loved every second of our time in the city!
Boston played an integral role in the founding of the United States, with many key events that led to the American Revolution. And the city is loaded with history around every corner. At times, it felt like we were just wandering around an outdoor museum!
Watch our experience in Boston, including part of the Freedom Trail, dumping tea into the sea, touring Fenway Park, and so much more!
But Boston has a lot more to offer than just history. It is a hotspot for Italian cuisine and seafood, home to the oldest MLB stadium in the US, has beautiful parks, cool neighborhoods, markets, and so much more. And with just 2 days in Boston, you can experience so much of what makes this city special!
In this guide we’re sharing a Boston itinerary for 2 days, plus tons of helpful logistical information to help you plan your trip. We hope you love the city as much as we did!
This 2 days in Boston itinerary and guide is sponsored by Tripadvisor, the world’s largest travel website. On Tripadvisor you can not only read traveler reviews on hotels, restaurants, and activities, but there are also 300,000 bookable experiences, like food tours, museums, boat cruises, and so much more!
In this guide we’ll be linking to some of these Tripadvisor experiences, but as always, we’re sharing our honest opinions based on our personal experiences.
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About this 2 days in Boston Itinerary
Whether you have a weekend in Boston or are visiting on a weekday, this 2 days in Boston itinerary is perfect for first timers who want to experience Boston’s perfect mix of history, delicious local eats, and city life.
We’re focusing this itinerary on things we personally experienced, plus spots that came highly recommended from friends and local followers. It’s a fast paced itinerary, but there are many ways to customize it for your interests or combine sites through tours.
We also are including a saveable Boston itinerary graphic at the end of this guide, so you can save an easy to read version to take with you on your trip!
Want to save some money while in Boston? If you book any of the tours or activities we’ve listed, or any other Tripadvisor experience around the world, use our code APLUSK10 for 10% off!
Day 1 in Boston
The first day of this Boston itinerary focuses heavily on history! Today you’ll experience most of the famous Freedom Trail, try heavily debated Italian treats, and more!
Enjoy breakfast and coffee
Start your day with coffee and breakfast. You’ll need some fuel to conquer the big day ahead! Here are a handful of coffee and breakfast options in various parts of town, ranging from quick coffee shops to sit down restaurants.
Coffee shops in Boston
- Thinking Cup (they have multiple locations and we really enjoyed their coffee!)
- Gracenote
- Ogawa Coffee
- The Well Coffee House
- George Howell Coffee
- Kohi Coffee Company
- Tradesman Coffee Shop and Lounge
Breakfast spots
- Tatte Bakery & Cafe
- Cafe Bonjour
- Capitol Coffee House (this is a hole in the wall, no frills spot with food served on paper plates)
- Mike & Patty’s High Street Place (get the breakfast sandwich!)
Want a unique breakfast experience? Go on an Underground Donut Tour where you’ll get to try multiple donut shops around town, while learning a bit about the city from a local guide!
Start your Freedom Trail exploring!
The Freedom Trail is a 2.5 mile (one way) pathway that connects 16 of Boston’s most historic and important sites. It is easily the most popular thing to do in Boston!
If you follow this 2 days in Boston itinerary you will be visiting most of the sites. There are a few sites we are not including, but if you follow the Freedom Trail, you will go by them and can stop if you choose. We’re also mixing in a couple non Freedom Trail stops this day, as they are along the way and worth checking out!
The itinerary for day one may look like a lot of stops, but many of them are super quick. Also, if you decide to do one of the tours we’re linking below, your itinerary for day one will look a bit different, as you’ll visit most of these stops on your tour.
A few things to know before completing the Freedom Trail:
- Look for the red bricks on the ground! The Freedom Trail is marked by red bricks on the sidewalk. We didn’t know this during our visit and kind of just wandered around randomly. But for the best path, follow the red bricks!
- The National Park Service app offers a free audio tour of the Freedom Trail, Black Heritage Trail, Bunker Hill, and more! If you really want to dive in on the Freedom Trail sites, these free audio tours would be a good addition.
- Most of the sites on the Freedom Trail have no admission fee, but some do. The Old South Meeting House, Old State House, Paul Revere House, and the Old North Church are managed by partner agencies and charge admission.
- Some of the sites you will just visit the outside and can access anytime of day, while others you may want to go inside. Make sure to check hours, as they can vary by day of the week.
For the best Freedom Trail experience, go on a Freedom Trail tour! While we explored on our own, going with a guide is truly the best way to learn Boston’s history. These guides are historical experts and can provide so much information that you may never learn on your own.
There are tons of options to choose from, but here are a handful that are highly rated. Bonus points if you choose one with a costumed guide!
Entire Freedom Trail Tour: Want to experience the entire Freedom Trail with a guide? This tour is for you! On this 4 hour tour you will check out every single stop!
The Revolutionary Story Walking Tour: This almost 4 hour tour will take you to many stops along the Freedom Trail. But instead of focusing on every site, they instead focus on telling the history of Boston, including tidbits not related to the Freedom Trail. Some guests on the tours are assigned characters!
Freedom Trail Daily Walking Tour: If you have less time, this is a great shorter tour. And it is led by a costumed guide! You will explore the sites from Boston Common to Faneuil Hall, so there will be some stops to still check out on your own.
Self Guided Audio Tour: Prefer to go at your own pace? This self guided audio tour will give you lots of historical information, but without an actual tour!
Granary Burying Ground
There are 16 historic burying grounds in Boston and the most visited is the Granary Burying Ground along the Freedom Trail. While there are only 2,300 markers, it is said that there are 5,000 people buried here, including Paul Revere and John Hancock, as well as victims of the Boston Massacre.
During our visit, many tours were stopped here. The benefit of this is that we got to hear some fun facts, but we also had to battle some crowds to see the most popular gravesites.
King’s Chapel and Burying Ground
Just down the street from the Granary Burying Ground is King’s Chapel. This chapel was founded in 1686 as the first Anglican church in Boston. You can take a couple different tours inside!
Right next to the chapel is the King’s Chapel Burying Ground, which is said to be the oldest in Boston. While the burying ground is smaller than Granary, it’s a lot less busy and still worth a quick stop! What we found interesting as we wandered through different burying grounds is seeing how different the tombstones all are. And also seeing how many are extremely slanted!
Boston Latin School
The Boston Latin School was the first public school in America back in 1635. At the time, it offered free education to males of all income levels, with one student being Benjamin Franklin. The original schoolhouse is no longer there, but you can see a mosaic and statue of Benjamin Franklin to see where the school site was.
Old State House
Boston is the capital of Massachusetts. And the Old State House acted as the seat of colonial, and later state government, throughout the 1700s. There is a New State House just down the road, but the Old State House holds a lot of history!
It was the site of the Boston Massacre in 1770, the first bloodshed of the American Revolution, and the Declaration of Independence was read for the first time in Boston from the balcony on July 18, 1776.
You can view it from the outside, but if you’d like to go inside, admission is $15 for adults. Your admission also gets you into the Old South Meeting House, which is another Freedom Trail site and where the Boston Tea Party began!
Faneuil Hall
Faneuil Hall was the first public meeting space in Boston and a great stop along the Freedom Trail. It is ironically known as “The Cradle of Liberty,” despite Faneuil getting much of his wealth from human enslavement.
Over its 280+ years it was home to many meetings, protests, and debates, as well as a marketplace. There are some exhibits on the first floor, which share some of the history of the hall. And you can go up to the second floor to see the Great Hall. Unfortunately during our visit, the Great Hall was not open. So make sure to check the hours here!
Visit a market
We love checking out markets when we travel. And Boston has several markets to visit, including both historic and new!
Quincy Market
Located right across from Faneuil Fall, the Quincy Market was built in 1826. Boston was rapidly growing and Faneuil Hall’s marketplace began overflowing with merchants. So they expanded just across the street!
Today, Quincy Market is a food hall and one of the most popular tourist spots in Boston. There are a variety of stands to get food from, plus some merchants selling souvenirs. We had heard it was pretty touristy and busy and while it wasn’t that busy for us (we went early on a Monday), it definitely felt touristy.
We’d suggest walking through, just to experience its history, but we have another market that we suggest grabbing food at instead!
Boston Public Market
We had heard that Boston Public Market was a great alternative to Quincy Market. And we loved it!
Boston Public Market is a newer market, opening in 2015, and focuses on New England food producers and artisans. Their mission includes supporting food growers and producers and cultivating a diverse community around food.
We really enjoyed the vibe of this market. It’s not huge, but it is really nice and has a good variety of vendors. Here you’ll find coffee, cider, pastries, seafood, flowers, produce, art, snacks, juices, a bar, and so much more!
We grabbed a frozen coffee from George Howell Coffee, which was perfect for a muggy day. Plus a bowl at Mo’Rockin Fusion, a Moroccan spot, that was bursting with flavor! There were many other delicious looking spots and we hear that The Popover Lady is another must try.
Since our next major stop involves food as well, we suggest grabbing a snack or splitting something so you have room for more food later!
Boston Haymarket
Just outside of the Boston Public Market is Haymarket, one of the nation’s oldest open-air markets, established in 1820. Here you’ll find tons of fresh, affordable produce, plus seafood.
However, it is only open on Fridays and Saturdays, so if you’re spending a weekend in Boston, make sure to check it out! It’s definitely on our list for next time!
Paul Revere’s House
One of the most important historical figures in Boston is Paul Revere. He was a silversmith that is most famously known for his midnight ride at the start of the American Revolution. More on that in a bit!
But while along the Freedom Trail, you can visit Paul Revere’s House, which is downtown Boston’s oldest remaining structure. You can view the house from the outside or pay to go inside and do a self guided tour (prices vary). Inside you’ll find a few rooms to explore, informational panels, plus museum interpreters to answer any questions. Just a heads up–photos are not allowed inside!
Eat Italian food in the North End
The North End is Boston’s oldest residential neighborhood and has been inhabited since the 1630s. In its early days it was occupied by 17th century Puritans and over the past four centuries, the area has been home to an African American community, and Irish, eastern European Jewish, and now more recently Italian immigrants.
By 1930, almost all residents were Italian. And because of this, there are many Italian restaurants, bakeries, and shops, even to this day!
You will naturally wander through the North End when visiting the next few Freedom Trail sights, so we suggest saving some room after your market exploring to enjoy an Italian lunch. Here are some must have food experiences!
Want to experience the best the North End has to offer? Go on a North End Walking Food Tour! You’ll not only get to try some delicious Italian eats, but also learn the history of the area!
Cheap Italian eats
There are tons of Italian restaurants in Boston, from fine dining to grab and go. For lunch, we’d suggest doing something quick, as there is still a lot to see today! Plus, you need to save room for cannolis 😉.
During our visit, we went to Galleria Umberto, a cheap, no frills, cash only spot. And we loved it!
We got their Sicilian style pizza, which has a thicker, airy focaccia like dough or crust and is often baked in a pan so that the edges and bottom are a little crispy. It was delicious! We also got arancini, which is a deep fried, breaded rice ball with mozzarella, beef, and peas. It was hot, cheesy, and super comforting.
Important note: this spot closes when it sells out, so arrive early!
For other quick eats in the North End check out Monica’s Mercato, Dino’s Cafe, and Regina Pizzeria. Want something a bit fancier? We’re sharing more Italian options later on for dinner!
Try a cannoli (or two)
An iconic food item in the North End are cannolis. It’s a must-eat while in Boston! And there is a huge debate about who has the best. Below are three of the top contenders, ranked in order of popularity.
Mike’s Pastry (Cash only)
This is hands down the most popular spot. It has been around since 1946 and while some say it’s overrated, others say the crazy lines are for good reason. We lucked out and only had to wait a minute, but be prepared to spend some time in line here!
Modern Pastry (Cash only)
Started in 1930, Modern Pastry was founded by the Picariello family, who brought their recipes, culture, and hospitality from Italy. One unique thing about this spot is that they fill their cannolis when you order, so it’s a little fresher. You get to choose your shell, filling, and topping.
Bova’s (Cash preferred)
Another bakery in the North End that’s very popular is Bova’s Bakery. They’ve been around for nearly a century, offering Italian specialty cookies, cannolis, pastries, pies, sweet Italian bread, and more!
So where did we go?
During our visit, we tried the two most popular spots, Mike’s Pastry and Modern Pastry.
From Mike’s Pastry, we got the Florentine (we heard it was the best!), which has a shell made of nuts and honey. It was SO good, especially the shell! From Modern Pastry we got a plain shell, with ricotta filling and pistachios. It was also heavenly!
Since these were two different styles, we can’t fully compare them. But I think we both agreed we liked the Florentine shell better and the filling from Modern better. If the lines aren’t too crazy, grab a cannoli from multiple spots!
Old North Church
The Old North Church was built in 1723 and played a very important role in the American Revolution. Remember Paul Revere from a minute ago? This is where he began his famous midnight ride!
Paul Revere asked three Boston patriots to watch for British troop movement and hang lanterns in the Old North Church’s steeple to send a warning to the waiting American militia across the Charles River. Revere said to hang one lantern if the British troops marched by land and two lanterns if they approached by sea. Two lanterns were hung, and Paul Revere and others began the ride to Lexington and Concord to warn that the British were coming.
The church is best viewed from the outside along Salem Street and you can purchase one of their tour options to visit inside. And as you walk to the church, make sure you stop at the statue of Paul Revere.
Copp’s Hill Burying Ground
The final burying ground along the Freedom Trail is the Copp’s Hill Burying Ground. This is Boston’s second oldest and is the final resting place of over 10,000 burials. One notable person buried here is Robert Newman, who is believed to be one of the two people who held a lantern in the steeple of the Old North Church.
USS Constitution
Your final two Freedom Trail stops will take you across the Charles River to Charlestown! This is an easy walk from the North End, with a sidewalk along the North Washington Street Bridge or a pathway by the locks.
Once over in Charlestown, make sure to head to the USS Constitution! This ship launched in 1797 and is the oldest commissioned warship afloat. It has sailed all over the world, including to the Caribbean, Mediterranean, Europe, the Pacific, and Africa. And has been involved in multiple battles, including the War of 1812, where it earned the nickname “Old Ironsides.”
There are a few ways to experience the ship. You can view it from the Paul Revere Midnight Ride Landing Site, go inside the ship, or visit the neighboring museum.
Going inside the ship
The ship is owned and operated by the US Navy and is free to enter. However, it is only open Wednesday-Sunday from 10 AM-4 PM. Since we visited on a Monday and Tuesday, we were unable to do this, but it looks really cool!
Note: Anyone 18+ must show ID to enter. So make sure you have it on you!
USS Constitution Museum
The USS Constitution Museum shares the history of the USS Constitution. It does not give you access to the boat, but is right by the boat. So if you’re visiting when the boat is open, you can easily combine them.
The Museum is open daily from 9 AM-6 PM and is donation based, with the donation suggestions ranging from $5-$15 depending on your age.
Tip: If visiting the museum is high up on your list, we’d suggest doing this on day two of this itinerary, so you don’t have to rush this experience!
USS Cassin Young
While at the USS Constitution make sure to visit the USS Cassin Young. It is free to enter!
Bunker Hill Monument
The final Freedom Trail stop is the Bunker Hill Monument. Back on June 17, 1775, this was the site of the first pitched battle between British troops and New England soldiers.
On top of the hill is now a 221-foot tall obelisk built entirely of quarried granite, which took 17 years to build. You are able to go climb 294 stairs to the top to see Boston from above. And it’s free to do so!
The monument is closed on Mondays and Tuesdays and you can see its current hours here. This was another spot we had to admire from afar, due to visiting early in the week.
Dinner
After a big, busy day of exploring Boston, end the day with a delicious dinner! There are tons of solid spots to choose from all around the city, but here are some options from a variety of cuisines!
Italian: Carmelina’s, Giacomo’s, Mamma Maria, or Arya Trattoria
Seafood: Warren Tavern ($1 oysters before 6 PM!) or Neptune Oyster
Mexican: Tenoch
Mediterranean: Oleana (a bit out of town!)
If you want a drink, head to The Bell in Hand Tavern, the oldest continuously operated tavern in the US, Trillium Brewing Company, or visit the Samuel Adams Taproom!
Day 2 in Boston
The second day of this Boston itinerary focuses mostly on spots outside of the famous Freedom Trail. You’ll explore a beautiful park, eat more iconic Boston foods, check out a museum, and more!
Since everyone’s interests vary, we’re including a handful of options today, so you can create your own perfect day!
Try a Boston Cream Pie
While in Boston, you have to try a Boston Cream Pie! It’s the state dessert of Massachusetts after all! But despite its name, Boston Cream Pie is not actually pie, it’s cake. It’s layers of sponge cake, with a cream filling between them and chocolate ganache on top. And oh boy, is it GOOD!
Boston Cream Pie was first created in 1856 at the Omni Parker House Hotel. And you can still eat it here today! At the bottom of the hotel there is a small shop where you can buy a Boston Cream Pie and other goodies.
However, for our Boston Cream Pie we went to Flour Bakery + Cafe and we highly recommend it. You may be thinking “cake for breakfast!?” Heck yeah! Rules don’t exist on vacation 😉. But the reason we suggest going to Flour Bakery + Cafe is because you can also get coffee and savory items to balance out the sweetness of the Boston Cream Pie.
Check out a museum
Spend the rest of your morning checking out a museum! There are a bunch of great museums in Boston, but here are a few that we’d suggest during your 2 days in Boston!
Boston Tea Party Ships & Museum
One of the most iconic events to take place in Boston is the Boston Tea Party. This was a protest by American colonists in 1773 against British taxes on tea. While disguised as Native Americans, they dumped British tea into the Boston Harbor, showing their resistance to unjust taxation and British control.
And the Boston Tea Party Ships & Museum is a great way to learn about the experience firsthand! During the tour you’ll be a part of a fun reenactment of the Boston Tea Party. The tour starts out with a town meeting, where you’ll get a character card (I had a speaking part!) and listen to your costumed leader. You’ll get riled up as you discuss the current taxation (fie!!!) and then go to the ship!
Once on the ship, you get to see the inside, take an oath, and then throw tea overboard! For the last part, you’ll see an actual tea crate from the Boston Tea Party and watch a video about it.
And when you’re done, you can pay a bit extra to sample the five teas that were dumped into the harbor. It’s totally worth the cost! Make sure to try the strongest one. It’s smoky!
Overall, we LOVED this experience! At the end of our 2 days in Boston, we agreed that it was easily one of our favorite things we did. It’s definitely touristy, but so much fun, especially if you really get into it. We embraced our roles and yelled huzzah as loud as we could!
Book your tickets to the Boston Tea Party Ships & Museum on Tripadvisor! You can save 10% by using our code APLUSK10. Which if booking for two people, can buy you an extra cannoli!
Isabella Stewart Gardner Museum
The Isabella Stewart Gardner Museum is an art museum tucked into what looks like a Venetian palace. It’s home to artwork that was collected by Isabella Stewart Gardner, a wealthy Bostonian, who passed away in 1924.
When she died, her will states that the museum was not to change in any way. While this is still true and the museum is how she laid it out years ago, they have added a new wing, to better accommodate its high amount of visitors.
Something else interesting about this museum is that it was also home to the biggest art theft in history! Back in March 1990, two thieves dressed up as police officers and broke into the museum, stealing 13 works of art. Crazy!
We admittedly aren’t really art museum people, but this place does look amazing! Not only does it have tons of beautiful artwork, but the building itself is stunning and features both indoor and outdoor spaces. It feels a bit more like visiting a palace than a traditional art museum.
Make sure to buy your tickets in advance. It does sell out! Note: the museum is not open on Tuesdays.
Museum of Fine Arts
The Museum of Fine Arts in Boston is a highly regarded art museum.There are 100 galleries of art and 500,000 pieces of work! Compared to the Isabella Stewart Gardner Museum, it’s more of a traditional art museum experience. But there are a ton of different styles of art to see, so there is something for everyone.
You can get your tickets in advance, but it is not required, except for some exhibits. Note: the museum is closed on Tuesdays.
If none of these museums appeal to you, you could also spend more time on the Freedom Trail, visiting the inside of some of the sights. There is no shortage of museums or interesting tours all around the city!
Have lobster and chowder for lunch
For lunch, grab two iconic New England food items: lobster and clam chowder! There are many places to eat both around town, but we went to James Hook & Co., which has been family owned and operated since 1925. They have lobster in a few different ways and super creamy chowder!
Another spot that came highly recommended is Boston Sail Loft. They also have some of the best chowder in the city and they add dill to theirs for a unique twist!
Wander through Boston Common and Public Garden
Boston Common is America’s oldest public park, established back in 1634! This park is technically on the Freedom Trail, but with so many other sights to see along the Freedom Trail on day one, we think it deserves more time than a quick stop!
At the park you can find fountains, monuments, lots of green space, city views, and even a spray pool for kiddos in the summer. We enjoyed our walk through this park, but don’t just stop here. The neighboring Boston Public Garden is a MUST as well!
This garden has so many colorful flowers, a pond that you can take a swan boat ride on ($4.50 per adult), plus more monuments and statues. One of which being the Make Way for Ducklings statue, which is inspired by Robert McCloskey’s 1941 children’s book. This was a popular spot in the park for parents to get photos of their kids!
Between parks you can also take a detour and wander around the charming Beacon Hill neighborhood!
Back Bay
Walking through Boston Common and Public Garden will lead you to the Back Bay neighborhood. This neighborhood is lined with gorgeous brownstone homes and you can find many local and brand name stores, plus tons of places to eat.
It is also home to the finish line of the famous Boston Marathon. And on April 15, 2013, was where the Boston Marathon Bombing occurred. You can see two different memorials along Boylston Avenue, remembering the three lives lost that day.
Boston Public Library
Our favorite stop in Back Bay was the Boston Public Library. This library is STUNNING! You will feel like you just walked into an art museum. But it’s a library. And it’s 100% free to visit!
The library has Renaissance style architecture, impressive columns, sculptures, paintings, and intricate details. There are various rooms to check out, plus an outdoor courtyard with a fountain. We were blown away by this place. It truly felt like we had been transported to a fancy museum or palace in Europe!
We spend a lot of time at libraries while on the road. They are our go-to spot for a free place to work and this was easily our favorite library we have ever been to!
Tour Fenway park (& see a Red Sox game!)
Adam’s top bucket list item during our 2 days in Boston was to see Fenway Park. Home to the Boston Red Sox, this is the oldest MLB ballpark, built in 1912. And it’s a MUST see for baseball fans!
During our visit we did the one hour Fenway Park Tour, where we got to walk all around the ballpark and learn tons of history and fun facts about Fenway and the Red Sox. Did you know Fenway is not symmetrical? Or that it has a rooftop farm?
We also got to sit on the Green Monster, which was so cool! Our guide Joe was the best and even the lesser baseball fan of the two of us (Kathryn) really enjoyed it!
Book your Fenway Park Tour in advance to make sure you get a spot! Not a baseball fan?Check out a tour of Harvard or visit another museum instead!
Not only do we highly recommend the tour, but if you visit during baseball season (April to September), going to a game is a must! We were lucky enough to time our visit with a game and had such a fun night at Fenway. You can view the Red Sox schedule here.
We realize not everyone is a baseball fan, but just experiencing the energy and history of this place is a classic Boston experience!
Tip: bags over a certain size are not allowed. We brought a small fanny pack and were fine, but if you have something much larger, you may have to store it nearby.
Dinner
After another fun filled day in Boston, enjoy dinner in Back Bay! There are countless restaurants to experience in this area, but here are some suggestions to get you started:
Mediterranean: We LOVED Greco, which is a fast casual Greek Spot. For something fancier, check out Krasi, which is owned by the same people.
Ramen: Hokkaido Ramen Santouka is a Japanese based chain with only a few US locations. And it’s said to be some of the best ramen in Boston! REDWHITE Ramen is another ramen spot in Back Bay with vegan ramen.
Burgers: Boston Burger Company or The Capital Burger for a fancier burger experience.
Can’t decide? Visit Time Out Market, a bit of a walk from Back Bay, to have a bunch of options all under one roof!
Dessert: Amorino is a popular spot for dessert!
Have more than 2 days in Boston?
While 2 days in Boston is a great amount of time to get a taste of its history and delicious eats, there is a lot more to do in the city and surrounding area. If you have additional time or just want more ideas, check out these other things to do in Boston!
Go on a whale watching tour!
From May to October, whales migrate to the North Atlantic, which makes for great whale watching around Boston! We have gone whale watching in Hawaii and Alaska and it is a magical experience.
This half day whale watching tour is a great option! You will have the chance to see humpback and fin whales, plus dolphins. And amazing scenery along the way!
Visit the Samuel Adams Brewery
For the beer lovers, Samuel Adams is quite possibly the most famous brewer in the Boston area. While there is a taproom downtown, if you want to take a brewery tour, you’ll have to make a bit of a trek out to Jamaica Plain.
Want to visit multiple breweries? Check out this brewery tour, where you’ll get to visit 4 different ones!
Take a day trip
Boston is close to many other popular spots in Massachusetts, including:
- Cape Cod (~1.5-2.5 hours one way, depending on where you go)
- Martha’s Vineyard (ferry required)
- Salem (~40 minutes one way)
- Other historical destinations, like Plymouth (~1 hour one way)
These are all relatively easy to get to by vehicle, but will take at least a day to experience.
Don’t have access to a vehicle? There are a handful of day trips you can book with a guide, including Boston to Plymouth and Martha’s Vineyard.
Go on a Duck Tour
For a unique way to tour the city, go on a duck tour! Despite what younger Kathryn thought when she went on a duck tour in Austin, you are not on a tour to see ducks. Instead, you’re riding a “duck,” which is an amphibious vehicle that can drive on land and float on water!
This duck tour in Boston takes you by many of the Freedom Trail sights and on the Charles River!
Enjoy a sunset cruise!
Want to see Boston under the golden sunset light? Take a sunset cruise! There are a variety of tour options to choose from, depending on what type of boat you’d like to be on.
The Boston Harbor Historic Cruise and the Boston Harbor Sunset Cruise will both take you around Boston Harbor and near the USS Constitution. You can also cruise on a historic sailboat as well!
Hike Blue Hills Reservation
Hiking is our favorite activity and even being in a big city, there is nature nearby! If you’re looking for a bit of exercise and some views, check out the Blue Hills Reservation. It’s just under a 30 minute drive from Boston and has a variety of hikes to check out!
Get a Go City Pass
As you plan your Boston trip, you will likely see the Go City Pass. This pass gets you access to over 40 paid attractions in Boston, at discounted prices. It can be a good deal if you plan to visit a bunch of paid spots, but it depends on what your goals are during your trip.
We suggest making a list of what you’d like to see, adding up the cost, and determining if this pass will be worth it to you. With us only having 2 days in Boston, it didn’t make sense. But it may be a good deal for you!
How to get to Boston
Boston, Massachusetts is located in New England, a region in the northeastern part of the United States. It is one of the major cities within the region, making travel to Boston pretty easy, with a variety of options.
Flying to Boston
The Boston Logan International Airport (BOS) is located only a 10-20 minute drive northeast of the main tourist areas of downtown Boston. As one of the major international airports in the US, it is serviced by just about any airline you would be flying in the US.
One very neat feature about the airport is that it has a ferry terminal! You can take a ferry from the airport to Long Wharf right in the heart of Boston. This makes for a fun way to get to the city if the ferry’s schedule works with yours. You can also take the “T” (subway) from the airport.
Taking the train to Boston
If visiting Boston from a nearby major city on the East Coast, you can take a train into Boston! Amtrak’s Acela Train stops in Boston, as well as Washington DC, Philadelphia, and New York City. We personally love train travel! It may take longer than flying overall, but it tends to be more spacious and you can see more scenery. We would love to do this someday!
Driving to Boston
If road tripping around New England, Boston makes for a convenient stop. Here is how long you can expect to drive from nearby popular destinations!
Note: One thing to keep in mind when driving to New England is that many routes have tolls. If you want to avoid paying for tolls, make sure to turn off tolls on your Google Maps settings. We were able to get around New England by avoiding tolls and didn’t spend too much extra time driving.
Providence, Rhode Island: 1 hour, 15 minutes
Newport, Rhode Island: 1.5 hours
Hartford, Connecticut: 2.5 hours
New Haven, Connecticut: 2.5-3 hours
Portland, Maine: 3 hours
New York City: 4-4.5 hours
Getting around Boston
Walking
Boston is a very walkable city. In fact, it’s said to be one of the most walkable in the US! We LOVED walking around Boston. It gave us the chance to see so much of the city, including many things we would’ve missed otherwise! Just make sure you wear good shoes, since you’ll likely walk a lot!
Public transportation
Boston also has one of the best public transportation systems, with subways, buses, and ferries. Depending on how long you’re staying and how much you plan to utilize the subways and buses, you can get a 7 day unlimited pass to cut costs!
Our advice would be to utilize both walking and public transportation to get around Boston.
Bluebikes
Boston has a public bike sharing program called Bluebikes, where you can grab a bike at various spots around the city and ride around! For visitors, you can pay $2.95 for a 30 minute ride or $10 for up to two hours at a time for 24 hours.
Rideshare
Similar to other large cities, there is also Lyft and Uber, so for any destinations that cannot be reached via the methods above, this is another option.
Do you need a car in Boston?
Unless you plan to do day trips to the surrounding area, you will not need a car in Boston. We’d actually advise against it, as paying for parking will add up and add an additional layer of complexity.
For our visit, we did not want to deal with our van in Boston, so we camped outside of the city and took the ferry every day. It worked out great!
When to visit Boston
The best month to visit Boston
Boston is a year round destination and the best time of year to visit depends on what you’re interested in, weather you prefer, and how many crowds you can handle. No matter what time of the year you visit, you’ll find a range of activities and attractions.
Spring in Boston offers milder temperatures, blooming flowers, and the city waking up after the winter. It’s finally pleasant enough to walk outside again and spend time at Boston Common and Public Garden. Baseball season kicks off in the spring and the Boston Marathon runs in April as well, so it is an exciting time to visit.
The summertime in Boston features hotel rates, temperatures, and crowds at their peak. It’s a great time for a Boston Red Sox game at Fenway Park, a boat tour in Boston Harbor, or a stroll along the Freedom Trail. Concerts and festivities will also be happening all around the city, so things are lively! Since summer is definitely the most popular time to visit, remember to pack your patience and know things will be busy.
For the most pleasant weather and, according to some, the most beautiful setting, plan your visit for the fall. The temperatures will likely be a little lower and the fall foliage will begin to show. This is when we hope to visit next time!
If you visit during the winter, you’ll likely see the city covered in snow and holiday decorations. You’ll likely notice less tourists too! Ice skating is a popular activity and if it gets too cold for you, you can always pop into a cafe, museum, or attend a theater performance.
Day of the week
As for timing, we did notice that a lot of things were closed on Mondays and Tuesdays. So if your 2 days in Boston fall on those days, keep that in mind. However, it didn’t bother us, as we were fine seeing things from the outside.
Time of day
We also noticed that many of the sights on the Freedom Trail do not open until 10 AM or so. We’d suggest not starting your days too early, as you may have to hop around and backtrack. We tried to structure this Boston itinerary so that you’ll do things that are open earlier first!
Where to stay in Boston
Boston has a handful of neighborhoods to stay in, each with its own advantages and unique characteristics. But, prepare yourself, staying in Boston is NOT cheap.
Below are some options in the most popular neighborhoods to stay in, plus a couple campgrounds for those in a van or RV like us. To see even more options, check out the best hotels in Boston on Tripadvisor.
Downtown
Downtown Boston is a bustling urban area and a great central location to base your stay. You’ll be close to many popular tourist spots, like Faneuil Hall Marketplace and Boston Common. Staying in the downtown area may be the most convenient, but you will pay for convenience.
Hotels
Courtyard by Marriott Boston Downtown/North Station
The Godfrey Hotel
DoubleTree by Hilton Hotel Boston – Downtown
Vacation Rentals
Boston Fidi Studio
King Bed Loft in the Heart of Downtown
Downtown Luxury 1BR
Back Bay
Back Bay is a picturesque neighborhood lined with gorgeous brownstone homes, plus lots of shops and restaurants. It is a really neat area and centrally located to many of the popular sites in the city. We loved walking around here!
Hotels
Fairmont Copley Plaza
Courtyard by Marriott Boston Copley Plaza
Boston Park Plaza
The Eliot Hotel
The Verb
The Revolution Hotel: This boutique hotel is not necessarily a hostel, although the rooms are private and many have shared bathrooms. They do also offer normal hotel style rooms!
Oasis Guest House: This is a more affordable option located in brownstones. USA Today rated as “Best Value in Boston”
Vacation Rentals
Great Back Bay Location
Cozy, Adorable 1-bedroom apartment
Elegant Back Bay Studio
Airy Back Bay 2br/2bath Gem
Beacon Hill
Beacon Hill is one of Boston’s oldest and most picturesque neighborhoods. It has narrow cobblestone streets, gas lamps, and is overflowing with history and charm!
Vacation Rentals
Prime Location | Beacon Hill & Financial District
Convenient Beacon Hill 1BR
Perfect Studio in Beacon Hill
Cambridge
Just across the Charles River, Cambridge is a great option if you’re planning on adding Harvard and MIT to your itinerary. Despite being away from the main tourist spots of Boston, Cambridge is still an easy public transport ride away. You can also save a little bit of money by staying out here!
Hotels
Kimpton Marlowe Hotel
Holiday Inn Express
Vacation Rentals
Roomy 2BR in Kendall Square
Lovely Kendall Square 1BR
Hip East Cambridge 1BR near Lechmere T Station
Camping
One of the cheapest ways to visit Boston is by staying at a campground. Which is what we did! You won’t find campgrounds in the heart of the city, but if you don’t mind taking public transportation, it’s a great choice!
We stayed at Wompatuck State Park during our visit and took the ferry into the city every day. Don’t let the $17 rate online fool you (it fooled us!), that’s only for Massachusetts residents. Non-residents can expect to pay $54-$60 per night. It’s a lot more than we normally pay, but is still much cheaper than a hotel in the city!
It was a nice, wooded campground with cell service and hot showers. Some other options near Boston include Minute Man Campground, Normandy Farms Campground (we met some subscribers who were staying here and they loved it!), and Winter Island Park.
Ready to explore Boston?
Pin our 2 days in Boston itinerary and guide to help plan your trip!
