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If you’ve read any of our other posts about Boston, you likely know how much we love it by now. We’ve got articles about the best foods in Boston, Boston Public Transportation, Boston Cruises, and even Fenway Park. After living there for years, we considered it our home for a while. We fully understand that living there isn’t for everyone. But anybody can visit Boston. Here is the best Itinerary for visiting Boston in 4 days.
Ready to head to Boston? Here are some handy resources!
Boston in 4 Days
Day 1 – Explore The History Of Boston
Walk The Freedom Trail
This is going to be the main activity for day 1 of 4 days in Boston. There are guided tours available which can give you more information about the different stops along the way. Below are all the landmarks you’ll see. For more context check out our post full of tips and tricks about walking the Freedom Trail.
- Boston Common & Boston Public Garden
- Massachusetts State House
- Park Street Church
- Granary Burying Grounds
- Boston Latin School/Benjamin Franklin Statue
- Old South Meeting House
- Old State House
- Faneuil Hall
- Site of the Boston Massacre
- Paul Revere House
- Old North Church
- USS Constitution
- Bunker Hill Monument
Visit the Boston Tea Party Museum
Starting from Boston Common the Freedom Trail will bring you to many wonderful spots. As you walk toward Faneuil Hall this is the perfect time to veer off track a little and head over to the Boston Tea Party Museum. Found on the water on the bridge towards the Boston Seaport, this museum lets you throw tea overboard like Bostonians did at the start of the American Revolution.
Quincy Market & Faneuil Hall
From the Boston Tea Party Museum it’s time to walk back to the Freedom Trail and take a break for lunch. Quincy Market has lots of options for lunch. It is a very lively place in downtown Boston. From here, you’ll be able to see the brutalist style of Boston City Hall.
While lunch is definitely needed, don’t miss going inside Faneuil Hall. The main area of Faneuil Hall is a shopping area combined with history. Head upstairs and you’ll find the meeting hall and all the artifacts this stop has to offer. Definitely worth checking out.
Check out the food that Boston is most known for! There are so many traditional Boston foods found in Quincy Hall.
Another place to veer off, before continuing on to the Freedom Trail in the North End, is the Boston Public Market. There are even more delicious restaurants here. I highly recommend the apple cider donuts, they make them fresh. Also, the Popover Lady is worth a stop.
North End- Freedom Trail
As you walk through the Freedom Trail in North End, you get to see some great parts of North End. I highly recommend stopping inside Paul Revere’s house. It is one of my favorite stops on the Freedom Trail. Something that isn’t along the Freedom Trail but is worth a stop is the Historical Chocolate Shop between Paul Revere’s house and the Old North Church.
Check out Captain Jackson’s Historic Chocolate along your walk. It is such a cool demonstration of how chocolate was made historically, plus you can taste it along the creation process. They also have a historic printing press next door.
USS Constitution Tour & Museum
This is one of my favorite stops on the Freedom Trail. As one of the oldest, still operating US Naval ships, the USS Constitution is an incredible ship to tour. Attached to the naval base is the interactive museum, giving you the history of the ship. Not only is it fun for adults, but also there are so many fun activities for kids. The museum shows you how the sailors lived on this ship.
Dinner at North End
After the USS Constitution, the Freedom Trail continues on to the Bunker Hill monument. I think it can be fun to see it, especially if you’re up for some more walking. If you’re tapped out, this is a perfect time for dinner! Head back over the bridge and walk back into North End.
North End is known for its incredible Italian food. There are so many amazing options available to you including plenty of dessert. After dinner, North End allows you to walk along the water to end your night. Here are some of our favorite places to eat in North End:
- Panza Restaurants
- Benventos Restaurant
- Monica’s Mercato & Salumeria
- Vinoteca di Monica
- Bova’s Bakery
Day 2 – Explore The Sports & Museums Of Boston
Day 2 of 4 days in Boston will involve traveling with Boston’s MBTA system. The trains and buses will take you through most parts of the city. There is so much to explore; each museum and stop is an option, but there are plenty of things to see in the general areas. Since we will be taking the buses and trains, I’d recommend getting the day pass for today. Be sure to keep it somewhere safe during the day.
Start the day with breakfast either at your hotel or at a cafe nearby. Then use the ProximiT app to find which bus or train stop is closest to get to our first location.
Isabella Stewart Gardner Museum
An art museum right in the middle of the city, the Isabella Stewart Gardner Museum, includes hundreds of pieces of artwork. At only $20 a ticket, it’s a good price for what it includes. They also have free tickets for the military, specific university students, and anybody named Isabella. Fun Fact; The Isabella Stewart Garner Museum holds the title of having the largest art theft in history and currently has a $10 Million reward for the return of the stolen paintings.
Museum of Fine Arts
Next door to Isabella Stewart Gardner Museum is the Museum of Fine Arts in Boston. While in Boston for 4 days, you might not choose to go to both museums, so definitely review both before picking one. This museum has so many exhibits that you might get a little lost inside (like we did).
Tour Fenway Park
This is probably one of my favorite things to do in Boston. The Red Sox stadium, Fenway Park, is an iconic baseball diamond. Here you can go on a behind-the-scenes tour of Fenway Park to learn some fun secrets. We did an entire post reviewing the tour and explaining everything you need to know about it.
Lunch in the Fenway Area
Next to Fenway Park is the Tasty Burger which is a local chain of delicious burgers in Boston. Additionally, there is the Time Out Food Hall with some great options. If you’re looking for a delicious bakery with lunch options, check out Tatte. It is my favorite place in Boston.
The Sports Museum- TD Garden
The Sports Museum is found in TD Garden. Since before lunch we went to the Fenway Tour, I figured it would only make sense that we go to the Sports Museum in TD Garden. TD Garden is where the Celtics and Bruins play. Additionally, this popular stadium also has shops and restaurants. Finally, from this museum, we will head over to the science museum.
Science Museum
A personal favorite of mine, the Boston Museum of Science is three floors of incredible displays and exhibits, many of which are interactive. With an interactive IMAX Theatre, Planetarium, and Theatre of Electricity (With the world’s largest air-insulated Van de Graaff lighting generator.) Prices range between $24 and $29 per person, but they have discounts for the military, along with a number of other discount programs to make it affordable for all. You’ll definitely want to spend the most time here.
Dinner & Exploring
From here we will take the green line train into Park Street then transfer over to the red line. For dinner we will be going into Cambridge then to explore Harvard. The stop you’ll take is the Harvard T Stop. This stop will bring you to the middle of the Harvard Square and right outside of the university.
There are plenty of places to eat here. Many of them are popular with the local students. While I don’t recommend getting Mike’s Pastries, however, I highly recommend stopping by JP Licks to get ice cream. There is also Union Donuts which are delicious as well. Check out our Donut Tour of Boston which includes Union Donuts.
One stop before Harvard is the MIT stop. It is MIT’s stop which also has great restaurant options if you’re interested in seeing MIT instead of Harvard. Here I’d recommend going to Happy Lamb for hot pot.
Day 3 – Explore The Modern Side Of Boston & Get Some Shopping In
While Boston is a city steeped in history, there are many aspects that have been modernized. We saw so much history in Boston on Day 1 of 4 days in Boston. Now we will be exploring some of those modern areas of Boston while possibly getting some shopping in.
Backbay
We will start our morning in Backbay. This is one of the most popular areas of Boston for shopping. Newbury Street has plenty of shops as well as plenty of places for breakfast. So we will be recommending breakfast on Newbury Street, there are a couple of delicious places like Stephanie’s on Newbury and Sonsie.
For your exploring time we recommend walking along Newbury Street, Commonwealth Avenue, and even walking over to the Prudential Center. The Prudential Center is a shopping mall as well as an apartment building. The Prudential Center is connected to another shopping mall so there is plenty to explore.
Charles River Esplanade
On the other side of Backbay you’ll find the Charles River. Along the Charles River is the esplanade. This is a park and walking path. In the summer it’s where the Boston Pops plays. In the fall you sit here to watch the Head of the Charles Regatta. It is a beautiful and scenic walk that is so fun for people watching as well. Running is a big deal in Boston so year round people are running along the river.
Stop at Cheers
From the popular Hatch Memorial Shell stage, you can cut through the Arthur Fiedler Footbridge and walk over to the Cheers Bar. The original bar is showcased in the popular TV show Cheers. While I don’t recommend having lunch here because it is a very touristy spot, it is definitely worth seeing, especially if you’re a fan of the show. They also have Cheer memorabilia for sale.
Beacon Hill & Lunch
A few blocks up from Cheers is Beacon Hill. This neighborhood is so cute and features the most photographed street in Boston. Of course, you’ll want to swing by Acorn Street to get photos. Charles Street is the main street for Beacon Hill, and here, you’ll find local shops as well as several great restaurants.
Boston Public Garden & Boston Common
Beacon Hill makes up the north side of the Boston Public Garden. In the spring, there are beautiful tulips blooming all over the garden. When there’s nice weather, there are plenty of performers throughout the public garden and Boston Common.
Chinatown
From here, it’s a short walk over to Chinatown. While it is not a very large Chinatown, it has many delicious restaurants and desserts. We enjoy getting dumplings there at the Dumpling King. Most places in Chinatown are really delicious. Of course, there are bakeries with traditional Chinese baked goods that are worth trying. Even though lunch was just had, it is a great place to get dessert in order to try something new.
Lawn on D
Lawn on D is a fun park in Seaport near the convention center. It has swings that light up different colors at night. Throughout the year they have concerts and other fun events. Additionally, they have giant Jenga and a bar. This is a fun place to take pictures as well. I would recommend taking the Silver Line to Lawn on D because it can be quite a long walk otherwise.
Seaport to Explore and for Dinner
We will close out day 3 of 4 days in Boston exploring the Seaport and getting some dinner. There is a beer garden at Trillium with local brews. Seaport Common has a variety of events throughout the year. In the winter it hosts a winter wonderland and in the fall there is always an Oktoberfest celebration. There are also plenty of spots to eat for dinner. The Barking Crab is very popular and on the water. Of course, there are plenty of places to shop.
Day 4 – Spend Time Out On The Water Of Boston
Our last day of 4 days in Boston! Since Boston is on the water, it is necessary to spend some time on the water during your trip! So, after breakfast, we will head over to the New England Aquarium.
New England Aquarium
The largest aquarium in New England, this is definitely a fun place to visit. There is a giant aquarium that goes through the middle of the entire aquarium with a ton of different sea creatures and fish. All the way at the top, you can sometimes catch sea turtle feeding times. When you first walk in, there is a large penguin exhibit, and there is also a sting ray touch tank. When you make it outside, you can see the sea lions playing.
Get your tickets to the New England Aquarium Here!
Harbor Water Tour
From the Aquarium, this is the perfect time to hit the water. There are two tours that I recommend. If you are visiting Boston for 4 days in Late March-November then I highly recommend going on a Whale Watching Tour. This is an incredibly unique tour and you get to see whales and dolphins.
If it is outside late March-November, then I recommend going on the famous Boston Duck Tours. The tour will allow you to see Boston from the water on a truck that is both land and sea. It is definitely a fun tour to take. Plus, the guides are always fun. There are so many different ways of exploring the Boston Harbor and so many tours available!
Get your tickets for the best Whale Watching Tour here. Get your tickets for the most fun Duck Tour here.
Seaport
After the boat tours are over, we will head back to the seaport. Although that was the last event last night, the area has a completely different feel during the day than at night. Plus, there are two fun museums to hit up while here. So take a stroll down by the water and go to the Boston Fire Museum and/or the Boston Children’s Museum. The seaport will also be a great place for lunch.
Boston Fire Museum
This is one of our favorite museums in Boston. Found inside a firehouse, this museum gives the history of the Boston Fire Department.
Boston Children’s Museum
A great museum for all who are traveling with children. This museum is on the water in Seaport and has so many fun activities for kids to enjoy. With three floors full of science and art activities, this is a place that can take hours of time if you wanted.
North End Food Tour
We will close out our time on the water by heading over to North End. Naturally, with the best Italian food around, it’s only right that the 4 days in Boston include a food tour. This fun tour will take you to try Clam Chowder in New England’s oldest restaurant, get the best lobster roll in town, and even savor some delicious arancini. Make sure to save room for dessert!
Where is Boston?
Boston is located in Massachusetts in the US’s Northeast. It is found on the coast and it is central to the rest of New England. Additionally, Boston is the capital of Massachusetts. Finally, the Greater Boston area includes many towns surrounding Boston along the water.
When To Visit Boston
Boston is a city that offers something for everyone year-round. The best time to visit is during the fall months. The crisp air and colorful foliage create a picturesque atmosphere. It is perfect for strolling along the historic streets or taking a leisurely bike ride through the parks.
Additionally, fall is when Boston’s famous sports teams, such as the Red Sox and Patriots, are in full swing. This creates an electric energy throughout the city. The abundance of festivals also makes fall the ideal time to experience Boston’s culture and community. The most popular events include the Head of the Charles Regatta and the Boston Book Festival.
Winter, which is about half the year, can get very cold, snowy, and icy, making many activities challenging. Summers can get very hot and humid at times, limiting how much time you can spend outside. Summer is also the busiest time of year for tourists and visitors. Spring is short and is a mix of too hot and too cold. Fall has fun activities and nice crisp, cool weather.
Why Visit Boston
Boston is a city that has a rich history and culture that offers visitors an unforgettable experience. It is a city that is known for its world-class museums, renowned universities, and delicious seafood cuisine. Visitors can explore the historic Freedom Trail, which takes them through some of the city’s most important landmarks. You can also catch a game at Fenway Park or take a stroll through Boston Common. Whether you’re a history buff, a foodie, or just looking for a great city to explore, Boston has something for everyone.
Wrapping Up: Visiting Boston In 4 Days
There is so much to do in Boston that 4 days barely scratches the surface. Having lived there for several years, we wanted this itinerary to get you to the most popular spots while introducing you to some local favorites. We highly recommend coming back another time for some day trips from Boston, either by train or driving, as well as exploring some of the other neighborhoods in Boston. Hopefully, this slice of American history mixed with modern Boston and time on the water gives you the trip of your New England dreams.
