Boston, MA is a city known for its deep historical roots, gorgeous architecture, and countless activities to enjoy. There’s truly something for everyone which makes Boston the perfect destination for a weekend trip. Read on for recommendations on how to make the most out of a 3-day trip to Boston!
This site contains affiliate links to products. I may receive a commission for purchases made through these links at no extra cost to you. There are only products included that I truly love. I APPRECIATE your support!
Table of Contents
How do I get to Boston?
One of the most convenient ways to get to Boston is through Boston Logan International Airport. Driving to the city is also a popular option, as Boston is located only a few hours outside of New York City, Philadelphia, and other major cities on the East Coast.
The Massachusetts Bay Transportation Authority offers several options for public transportation in the Boston area. Buses, commuter rails, and the subway are all common ways to navigate the city, and certain areas are very walkable. A rental car is not necessary to enjoy Boston, as there are also plentiful rideshare services available.
Tip!! Use the Discover Cars Search Engine to find the best deal on cars for your weekend in Boston.
What is the best time to visit Boston?
Summer and fall are the best seasons to visit Boston for pleasant weather and to enjoy seasonal outdoor activities. While summer is one of Boston’s most popular seasons, it is worth a visit if you’d like to attend some baseball games or outdoor concerts. Fall, meanwhile, will bring cooler temperatures that make exploring the city on foot very enjoyable. Fall is also a great time to visit if you are a fan of fall foliage.
Where should I stay in Boston?
Boston is home to a number of distinct areas and neighborhoods, but two great options to consider are downtown and Back Bay. If you want to be in the heart of the action and have the ability to walk among restaurants, shops, and activities, downtown is the place to be.
Staying downtown will put you near some of Boston’s most popular attractions, and you’ll be in the perfect place to explore the city’s nightlife. The Bostonian Boston is an upscale hotel with a reasonable price tag in the heart of downtown, while CitizenM Boston North Station Hotel is a little more pricey with sleek, luxurious rooms.
For fans of architecture and history, Back Bay is another great option as well. Back Bay is located along Newbury Street, one of Boston’s best areas for shopping and dining. Back Bay is full of historical buildings and homes and is considered a very upscale neighborhood within Boston. Hilton Boston Back Bay offers a standard hotel experience while The Charlesmark Boutique Hotel is perfect for those seeking a more unique stay.
Sample 3-Day Boston Weekend Itinerary
Day 1 in Boston
Morning
Start your morning right with a cup of coffee from the iconic Polcari’s Coffee. Polcari’s has been in operation for almost 100 years, making it a true Boston institution. The shop serves up classic drinks and Italian delicacies, and is one of the city’s most well-known and loved coffee shops.
Take your coffee to-go and enjoy a stroll along the Freedom Trail, a 2.5-mile-long path through the city that will lead you by some of Boston’s most iconic landmarks. Experience history firsthand as you walk by the Paul Revere House and the USS Constitution, and get a feel for the city as you discover shops, museums, and more historical sites along the way.
Afternoon
One of the best ways to experience Boston is by its many iconic breweries, including the original Samuel Adams Brewery. You can visit the brewery on your own and enjoy a meal and some drinks, or you can schedule a full tour of the historic facility. Even if you’re not a big beer drinker, it’s a fascinating experience to learn about the history of Boston and the brewery itself. Other well-known Boston breweries include Trillium Brewing, Harpoon Brewery, and Cambridge Brewing.
Speaking of Cambridge, a visit to Boston’s sister city is a must. Located just across the Charles River from Boston, Cambridge is notably home to Harvard University. The campus is known for its history and architecture, and visitors can enjoy a stroll through Harvard Yard, the oldest part of Harvard University. There are also a number of museums and shops throughout Cambridge, so you can truly enjoy the area for a full afternoon.
Evening
Catching a game at Fenway Park is an absolute must on any trip to Boston. Fenway Park is an iconic stadium and home to the Boston Red Sox baseball team. If you’re not able to watch a game at Fenway Park, another great option is to take a guided tour. You’ll be able to walk through various parts of the stadium and learn about its 100+ year history.
Not into sports? Grab a bite to eat and a drink at one of Boston’s many rooftop bars!
Day 2 in Boston
Morning
The perfect start to day 2 is a visit to Boston Common, a large park in the heart of the city, and the oldest city park in the United States. With beautiful landscaping and a number of landmarks dedicated to the park’s rich history, Boston Common is a great place to wander around and explore. Whether you like to run, bike, or just walk, Boston Common is sure to bring you a sense of relaxation.
If you’d prefer to spend your morning indoors, consider visiting one of Boston’s many museums. The Museum of Fine Arts is one of the best art museums in the world, while the Boston Tea Party Ships & Museum is an immersive experience perfect for history buffs.
Afternoon
Faneuil Hall Marketplace is the perfect afternoon destination to do some shopping and grab a bite to eat. The marketplace is home to a number of vendors who sell everything from clothing to souvenirs, books, and more. There are also a number of dining options in the marketplace that cater to all kinds of dietary preferences and restrictions.
Evening
If you haven’t yet gotten your fill of shopping, a stroll down Newbury Street is a great way to spend an evening in Boston. Newbury Street, located in Boston’s Back Bay neighborhood, is well-known for its shops and restaurants.
The street is lined with historic townhomes that various retailers have come to occupy, and you’ll find everything from pop-up kiosks to high-end designer stores. Newbury Street is also a great place to find dinner and drinks after a full day of shopping. You can often find festivals and live music along the street, so make sure to check their website in advance to see a schedule of upcoming events.
Day 3 in Boston:
Morning
Brattle Book Shop is a must-visit spot on any trip to Boston, and the perfect way to kick off day 3 of your adventures. The bookstore is one of the largest and oldest in America and contains a number of used books as well as a whole floor of rare publications. Brattle Book Shop is full of character and a great way to experience a slice of Boston culture.
Afternoon
Spend your last afternoon in Boston exploring the city by air. Boston Helicopters is one of the most popular companies offering helicopter tours in the Boston area. They have a number of packages to choose from depending on specific sights you want to see, and you’ll be truly amazed by the opportunity to see a city from above. Taking a helicopter tour of Boston is a unique experience you’ll never forget, and a pretty epic way to close out your trip.
Evening
Time Out Market is an upscale food hall located in a massive venue with over 25,000 square feet of space to enjoy. Time Out Market is a unique dining experience that highlights some of the best food and drinks the city has to offer. There are more than 10 vendors inside the market that serve up everything from Italian, Mexican, seafood, and even gourmet pastries. If you’re an indecisive eater and like to have options, Time Out Market is the perfect spot for you. All the food is sure to be delicious, and you’ll remember your dining experience for months to come.
Other things to do in Boston
- Explore the Franklin Park Zoo ($19.95 for adults, $17.96 for seniors 62+, $13.95 for kids 2-12)
- Keep your eyes peeled for whales and wildlife aboard this Whale Watching Cruise!
- Check out the city via trolley tour or historical boat cruise!
- Enjoy the unique architecture of the Hatch Shell, an outdoor concert venue
- Visit the beautiful Isabella Stewart Gardner Museum ($20 for adults, $18 for seniors, $13 for students)
- Take a guided scavenger hunt around Boston. You can choose from a haunted ghost tour, exploring murals, bar crawls, or several different hisotry tours.
Other tips to know before visiting Boston
The weather can often vary in Boston so you’ll definitely want to come prepared with layers. Comfortable walking shoes are also a must given all the adventuring you’ll be doing!
3-day Boston Weekend Trip Itinerary Recap:
- Day 1: Freedom Trail, Brewery Tour, Harvard, Fenway Park
- Day 2: Boston Commons, Museums, Faneuil Hall Marketplace, Newbury Street
- Day 3: Brattle Book Shop, Boston Helicopters, Time Out Market
One Weekend In Boston Isn’t Enough
As you can see, there’s SO much to do in Boston that one weekend would never be enough to see it all. You can customize your 3-day Boston itinerary based on what interests you. No matter what you’re looking for, you’ll find plenty of entertaining activities to create your own fun-filled, jam-packed adventure weekend in Boston!
What else would you add to this “One Weekend in Boston” Itinerary?
Tip! Make sure to follow me on Instagram for more USA weekend getaways and dog-friendly adventures!
Want an easier way to plan your Weekend Trips?! Click the picture below to download your FREE Weekend Getaway Planner!
Recent Posts
Pittsburgh is a world-class destination, full of character and personality. The city is full of interesting nightlife, attractions, sports, and nature, ideal for any type of traveler. It is...
One Weekend In Philadelphia: A 3-day Philadelphia Itinerary from a Local
Calling all history and art lovers!! Philadelphia is a city rich in history, full of museums, home to the infamous Rocky Steps, and of course the Philly cheesesteak. There’s definitely no shortage...