3-Day Boston Itinerary
- 1 3-Day Boston Itinerary
- 2 Boston Travel Tips for Your 3-Day Trip
- 3 What to Do in Boston in 3 Days
- 3.1 Day 1 in Chicago
- 3.2 Day 2 in Boston
- 3.3 Day 3 in Boston
So, you are thinking of visiting Boston, Massachusetts, and are wondering about the best things to do in Boston in 3 days?
Well, you have come to the right place. This 3-day Boston itinerary will help you decide the best way to spend your time and what to do and see in this historic American city.
Boston is the largest city in the state of Massachusetts and also its capital. But Boston is even more famous for the part it played in US history, including during the American Revolution. Founded in 1630, it is (by American standards) an “old” city.
You’ll find many historic landmarks and sites, cobblestone streets, and buildings that date back to Boston’s roots.
The post was written by Rebecca
Boston Travel Tips for Your 3-Day Trip
But before we get to what to do in Boston in 3 days, here are some travel tips to make your stay smoother.
How to Get to Boston
By air: If you are flying into Boston, you will be arriving at Logan International Airport (BOS), which is located only 4 miles from the city center. You can easily grab a taxi, subway, or even a water taxi from the airport to your hotel downtown.
By car: If you are driving in, then you can take Interstate 84 from the south, Interstate 90 from the west, or Interstate 95 from the north. (Keep in mind that parking is hard to find in Boston, and your hotel will likely charge you per day to park in their garage.)
By train: Public transportation is great in Boston, so you can also take the Acela high speed train into the city.
Weather in Boston
The weather in Boston is really nice, if a little humid in the summer, so this is the best time to visit (along with spring and fall). The average temperature at the height of summer in July is between 66ºF and 82ºF. Rain is moderate throughout the year.
If you decide to visit in the winter, it is definitely a bit colder. The average temperatures in January are between 22ºF and 37ºF. New England winters are no joke and you will see the most snow in January and February.
What to Pack for a Boston Trip
If you are coming in the spring, summer, or fall, you can usually just pack light clothes, like jeans, t-shirts, shorts, and dresses. Bostonians aren’t known for their high fashion and tend to dress according to the weather. Boston is also a big college town, so the basic jeans-and-shirt look works all year round.
If you are coming in winter, make sure to pack a warm jacket (preferably waterproof), scarf, gloves, and hat (bonus if it’s a Red Sox one – Boston takes their sports seriously).
Sneakers are fine since you will be walking a lot (though locals prefer loafers). And boots are a must during the snowy, winter weather.
Where to Stay in Boston
There are a lot of possibilities for accommodations in Boston, some with a lot of charm and history. Here are a few suggestions for different budgets during your 3 days in Boston.
For a luxury hotel, try the Fairmont Copley Plaza, which is located in the Back Bay area of the city and is close to popular spots, like Newbury Street. It’s a historic building that’s been redone with modern décor, and particularly favored by couples.
A midrange option would be the Revere Hotel, which has a great location right near beautiful Boston Common and the Visitor Center. It’s also very sleek and modern.
There are not a lot of budget hotels in Boston, but the HI Hostel would be a great choice for couples and solo travelers, with a breakfast provided and private rooms with en suite bathrooms. Located near Boston Common as well, it offers easy access to public transportation.
How to Get Around Boston
One of Boston’s nicknames (besides “Beantown”) is “the Walking City.” So, bring your walking shoes as you explore the city and the destinations on this itinerary that are nearby each other.
Other than that, public transportation is the way to go. Trains, trams, buses, and subways can be found all over the city and are the cheapest and most convenient way of getting around Boston. You can easily buy one-way paper tickets (known as “Charlie Tickets”) at most stations for $2.75.
If you want to get a Charlie Card, you can preload it and rides are only $2.25. This also offers a free transfer to the buses. There is a 7-day unlimited card, but this might not be worth it for this 3-day itinerary in Boston.
If you drive your own car or a rental, expect an on-site parking fee at most hotels, as well as difficulty parking as many areas require a residential-only neighborhood permit.
More Travel Tips
When you stay in Boston for 3 days you should know that Boston is an expensive city. And hotels are no exception. The most expensive time to visit Boston is in mid-May (when many of the colleges are having graduation ceremonies) and in September/October (conferences in town and visitors coming for the changing of the leaves/fall foliage).
A lot of buildings and hotels in Boston are historic and converted over the years, but they still retain things like no elevators, steep stairways, etc. Europeans may not find this unusual, but Americans from other cities may be surprised. If you need accessible hotel rooms or want central air conditioning, check before you book.
Boston also has a lot of brick and cobblestone streets, which can be tricky when wearing high heels or in the snow. Just be aware as you make your shoe selection where you will be sightseeing.
It is actually illegal in Boston to have happy hour drink specials. Instead, they offer food specials from 4pm-6pm.
Smoking marijuana is illegal in public, but the purchase and possession of it is legal in Massachusetts. Just don’t take it over state lines.
This is not a 24-hour town. Boston mostly closes up by midnight (bars at 2am) and the last subway leaves at 1230am. There are, however, a few all night supermarkets, restaurants, and night clubs.
Boston is a safe city so long as you use common sense and proper precautions. Avoid side streets after dark and subway stations late at night if you are alone. Keep your possessions close to you at all times. And probably avoid the more crime-ridden areas of Roxbury and Dorchester.
What to Do in Boston in 3 Days
Let´s get started with the Boston itinerary.
Day 1 in Chicago
Day 1 starts at the lovely and centrally-located Boston Common. This is easy to reach by bus or might even be within walking distance of your hotel (if you chose one of the suggestions above).
This is actually the oldest city park in the US, dating back to 1634. In the center of the park, you’ll find Frog Pond, a reflecting pool that makes a nice place to sit and enjoy the early morning light.
In the winter, it’s turned into an ice skating rink and even has a skating school nearby. In summer, it’s a spray pool. There’s also a children’s carousel, so this is a great stop for visiting families.
It’s also the official starting point for our next Boston attraction. After an hour or so, we can head there.
This is a path that is lined with red bricks and connects a lot of the famous historic landmarks of the city.
The trail is about 2.5 miles long and the best way to see the trail is on foot, and you can enter and exit it as you like. Some of the sights you will see are the Park Street Church and the Benjamin Franklin statue.
Depending on if you walk the entire trail or not, you will probably be done in 2-3 hours.
Our next stop will be a great place for snacks and souvenirs. It’s about 10 minutes by subway or 15 minutes on foot.
Faneuil Hall Marketplace
This marketplace is huge, encompassing four different historic buildings from the early 1800s that have been converted into a place for shops, restaurants, and even a promenade.
Faneuil Hall is an indoor/outdoor mall and eatery. Besides the North and South Markets, the other famous building is Quincy Market (and a favorite among locals and tourists).
Quincy Market is a very lively and exciting place, perfect for souvenir shopping, tasting local delicacies, and just wandering. If you like chess, there are tables set up for anyone who wants to stop for a game. And if you have ever seen the American TV show Cheers, a replica of the bar is here, too.
This market deserves at least a few hours of your time. It’s a lot of fun and a great place to eat a meal. Then, head to our next destination, about 10 minutes away on foot.
Old North Church
If you like historic churches, then the Old North Church is a good stop. Founded in 1722, it was made famous as the place from which Paul Revere received the signal that the British had arrived, which led to the Battles of Lexington and Concord in 1775.
This is an interesting stop for families, couples, or solo travelers.
You’ll even find a bust of the first American president, George Washington, inside. After a half hour here, you will probably be ready for our next stop on this Boston itinerary. It will take about 30 minutes by train.
The Charles River Esplanade is located in the Back Bay area of the city. It is also located on the south bank of the Charles River Basin. This park is a nice place to picnic or just relax and wander.
Take a breath and enjoy the cute, picturesque bridges, lush grassy areas, and view of the water. Then, head to our last stop of the night (15-20 minutes by either train or on foot).
Families, solo visitors, and couples alike will not want to miss this spot. The Skywalk Observatory offers amazing views of Boston because it is the only place in the city that has an elevated 360-degree perspective.
Located in the Prudential Tower, you can also learn a little bit more about Boston’s history by taking the audio tour that is available. Or just come for the views.
They are definitely worth it (especially at night), and the perfect way to end Day 1 of this Boston itinerary.
Day 2 in Boston
Day 2 starts with another charming outdoor area in the middle of Boston. After breakfast, let’s head to one of the city’s most popular public gardens.
Boston Public Garden
This garden was created in 1634 and went through a few changes in the Victorian Age to become the haven of plants and flowers that it is today. It is located right next to Boston Common.
You’ll find over 80 different local species, some a result of new techniques like hybridization, as well as exotic trees and plants. All of this gives the garden a gorgeous, colorful, and vibrant feel that is really nice to stroll through.
Besides the plant life, another very popular thing to do here is take a ride in the Swan Boats on the lake. Over a 100 years old, these boats are a fun activity for adults and kids alike. If you want to just sit back and relax though, grab one of the many benches and enjoy the morning.
This stop should take a couple of hours. Then head to Mary Eddy Baker Library and a fun attraction inside, about 15 minutes away by train.
The Mapparium is a free area within the library, which itself is a popular spot with its 1930s neo-classical architecture. But this fascinating section is a must-see when in Boston.
Built by map-guru Rand McNally in 1935, it is a 3-story, stained glass globe that can be seen from the 30-foot-long bridge through its center. It was built with the idea of seeing the countries of the world in accurate geographical relationship to each other.
You’ll also notice the changes that have taken place in borders and even country names.
But even if you aren’t a huge geography buff, the Mapparium is breathtakingly beautiful and too pretty to skip. Half an hour is all you need to take in its charms.
You may also want to stop and get a bite to eat. Then let’s try something a little different. Grab the train 10 minutes west (or a 15-minute walk).
Fenway Park Tour
I mentioned that Bostonians take their sports seriously and you’ll be hard-pressed to find anyone here who isn’t a Red Sox fan. And Fenway Park is where they play.
This baseball stadium is the oldest in the country, and relatively small, but has hosted numerous baseball, soccer, and hockey games, as well as religious and political rallies.
Take a fun tour of the stadium and see the players’ club houses, the press room, and the seats that are above the infamous “Green Monster,” which is the 37-foot-high wall in left field that is very difficult to hit a ball over because of its proximity to home plate. This is a fun tour for families and any sports fan.
When you’re done seeing Fenway, let’s head over to another cultural landmark in the city, albeit of a very different sort.
This is a 10-minute train ride, but I suggest walking it for the same amount of time through the “Emerald Necklace,” which is a series of city parks.
Museum of Fine Arts Boston
This museum is one of the oldest in the country, and also one of the most comprehensive. It houses 450,000 pieces of art, so I don’t think you’ll get through it all today!
But, your ticket does allow for a free re-entry within 10 days of your first, so if you can’t get enough on Day 2, you can come back tomorrow.
Take in the vast collections, galleries, and architecture of the building itself. This is a great destination for solo travelers, couples, and families that enjoy art and strolling through beautiful things.
Tips: To save on the $25 entrance fee, consider planning your trip for a Wednesday after 4pm when the museum is free and open late, until 9pm. Also, check their website for any free days that are coming up.
This stop could take you a few hours, depending on how much you love fine art. But take your time because our last stop of the night is open late. Stop for dinner and then grab the train 10 minutes east.
Wally’s Café Jazz Club
This cozy club is a great way to end your evening. One of the oldest continuously-running jazz clubs in the US, old-school jazz and blues are performed here nightly by students and locals. Sit back, have a cocktail, and enjoy the talents of the local musicians.
Tip: Bring cash. They may take cards, but cash is easier at this little spot.
If you’re visiting with family, Wally’s may not be the best spot for you and your kids, so my alternate suggestion is take the family about 30 minutes east by train to try a Boston tradition.
South Boston Candlepin bowling is tougher than regular bowling and a fun nighttime activity for pretty much anyone, but kids especially will love the challenge.
And that’s the end of Day 2. Let’s see what the last day of our itinerary has to offer.
Day 3 in Boston
For Day 3, let’s begin at a fun and lively area of the city.
The Lawn on D
Morning outings to the green areas of Boston seems to be a theme, but don’t skip the Lawn on D because it isn’t like other parks here.
This grassy area is nice for picnics and relaxing, but people really come here for the events and games. If you’re coming in the warm parts of spring or fall, and especially in summer, you can enjoy an area devoted to fun and silly lawn games, as well as oft-scheduled outdoor events. There are also concessions so you can grab a snack when you work up an appetite.
Speaking of food, I hope you have been trying some of the local cuisine. And if so, I suggest either Flour Bakery or Mike’s Pastry for a chance to try one of Boston’s most famous desserts: Boston Crème Pie.
The Lawn on D can be a lot of fun, but we still have other stops – so after a couple of hours, let’s head north for a different kind of museum – one on the water! You can walk or take the train, either way will take about 15-20 minutes.
Boston Tea Party Ships and Museum
The Boston Tea Party was an important event in American History and now you can visit the museum that’s been created to share artifacts and information about it – on a ship!
This is a fun stop, with interactive exhibits, actors playing out the scene, and even the chance to throw some tea overboard yourself. There’s a café and gift shop as well on this restored ship that you can check out when you’re done. This stop takes about 1-2 hours.
Then, it’s off to one of the most famous neighborhoods in Boston, about a 25-minute train ride.
This area is full of Federal-style row houses and is often what you see depicted in movies about the city. It’s also the most-desirable part of Boston to live in.
Stroll the brick sidewalks and narrow streets that run through Beacon Hill, through Charles Street and Louisbourg Square. Adorned with charming lampposts, the area is full of cute cafés and small shops, as well as luxurious residences.
After an hour or so, you can head to a particular favorite of families, or for those of us who are kids at heart (about 25 minutes by train).
The Boston Children’s Museum
Created in 1909 by local science teachers, the Boston Children’s Museum is a fun, hands-on learning and playing environment that is popular for locals and tourists alike.
There are tons of exhibits and the educational aspects are perfectly complemented by the fun of digging in and doing a wide variety of activities.
Check out the sculpture on the first floor that children can safely climb – up 3 floors! This is a great place for families, as it’s clean, safe, and well-run. It’s also a lot of fun, especially if you are visiting in the winter and want to spend a few hours warming up.
Our last stop for Day 3 is the picturesque Harborwalk, located about 30 minutes north and across the water.
If you’ve had dinner, this is a great place for an after-meal walk. The Waterfront Trail skirts along the edges of piers, wharves, beaches, and the shoreline.
Particularly on a warm summer evening, this is the place to go. Join other locals and tourists, from families to couples to singles, who are enjoying some fresh sea air and exercise while taking in some lovely areas of the city that haven’t yet been seen.
The Harborwalk is actually in the process of being expanded, and once done, will be almost 46 miles long in total. But for now, enjoy the walk, the views, and the art that is placed throughout.
Take in a sunset or see the glitter of the city lights from this new vantage point. This is a lovely way to end your visit to the city of Boston.
I hope this itinerary has given you a good idea of where to go in Boston in 3 days. There is a lot of history and fun to be had in this popular American city, and 3 days in Boston may not be enough to see it all, but this list gives you the highlights and will hopefully enable you to plan your own exciting Boston trip soon.
About the Author:
This post was written by Rebecca, who runs her own blog at The Journey at Home – where she writes about her life as a mother of 5 with everything that comes along with it. She lived in New York for a long time before she moved to Las Vegas. She also works as a freelancer for Arzo Travels.