Known as the “Cradle of Modern America,” Boston is one of the most historic cities in the United States. Everywhere you look in Boston, you’ll stumble across a place of historical significance, from the “Tea Party” at the Boston Harbor to the Old North Church, where the two lanterns once alerted that the British soldiers were coming up the Charles River.
Today, Boston is not only a hub for history but also beautiful art and architecture, one-of-a-kind shopping, and delicious dining. Boston is also known to be a college town, with over 100 schools in the area.
And those colleges affect when the best time to go to Boston is. Unlike many other travel destinations in the United States, Boston is often at its quietest in the summer, when most of the college students have returned home at the end of their semester. So, if you’re looking for a more peaceful visit, you may want to go in the summer!
That said, there’s no bad time to visit Boston, as long as you’re willing to brave the cold. In the winter, Boston temperatures can hover around freezing, so be sure to bundle up. But if you’re ready to travel in the winter, you’ll discover beautiful holiday displays, ice-skating on the iconic Frog Pond, and the wonderful Beacon Hill Holiday Stroll, where you’ll do some holiday shopping with a hot cocoa in hand.
Spring, when the weather warms up a bit, brings about two of the busiest times to visit Boston: the Boston Marathon weekend and St. Patrick’s Day. The Boston Marathon, held on the third Monday of April, known as Patriot’s Day, is a Boston tradition dating back to 1897. It’s the world’s oldest marathon and brings in over 20,000 runners from around the world each year.
Boston has a strong Irish heritage, which is why it’s often considered one of the best places to be for St. Patrick’s Day. From the annual parade to the traditional Dropkick Murphys concert, people come from all over to celebrate the holiday here.
Planning a long weekend trip in Boston? With so much to do and see in this historic city, it’s tough to know where to start. That’s why we’ve put together a 3-day Boston itinerary to help you see all that you can of Boston. Follow these recommendations, from where to eat to what to do, and you’re bound to have an amazing time exploring Beantown!
If you’re still deciding where to stay then make sure to check out our article on the best boutique hotels in Boston!
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How to Spend a Weekend in Boston, Massachusetts
Getting Around Boston
If you’re flying into Boston, you’ll most likely land at Boston Logan International Airport. To get into the city, you have many different options. You could always simply hop aboard the T, Boston’s mass transit system that connects the city and surrounding communities. Both the Blue Line and the Silver Line have ways to get you from the airport into the city.
You could also take the Logan Express, which will get you between the airport and Boston’s Back Bay. For a more scenic form of transportation, you could also take a water taxi from the Logan Airport to several areas around Boston, like the North End.
Not only is it unnecessary to rent a car to get around Boston, but it’s also not recommended. Boston is a very old city, and the streets are rather narrow and often difficult to navigate if you’re new to the area. Some areas of Boston don’t allow cars at all, meaning that you’ll have to park rather far away to get to those locations.
The city is very walkable, with many attractions within a small area. If you rent a car, you may find yourself simply leaving it parked all day. Though, you’ll have trouble finding parking in the first place. Boston’s public transportation system will get you around the city just fine. Get yourself a Charlie Card on your first day in town, and use it throughout your trip to hop abroad the T.
Boston Weekend Itinerary – Day 1
Compared to many of the United States’ major cities, Boston is fairly small, but there’s so much packed into it. So, it’s hard to decide just where to start. But for the first day of your 3-day Boston vacation, you should start over in the Beacon Hill area.
Beacon Hill’s Acorn Street
Beacon Hill is a historic neighborhood in Boston that’s as pretty as a picture. In fact, Beacon Hill’s Acorn Street is purportedly the most photographed street in the country. With its cobblestone roads lined with antique lanterns and rows of brick houses, it’s one of the most beautiful areas in the city!
Beacon Hill’s Charles Street
Over on Beacon Hill’s Charles Street, you’ll find a breakfast place that should kick off your 3 days in Boston. The Paramount is breakfast at its best, and it’s been serving up its comforting treats since 1937. You can’t go wrong with its buttermilk pancakes, but for an even more decadent meal, grab the Nutella waffle.
Once you’re done eating, you’ll want to spend some time exploring Charles Street and walking the famous hills of Beacon Hill. Charles Street is filled with boutique stores, chocolate and other sweet shops, and places to sip everything from fine wines to fresh juices.
Chinatown
Take a short scenic walk from Beacon Hill to the lovely and vibrant Chinatown, where you’ll find a one-of-a-kind spot for lunch. Empire Garden serves dim sum daily, but while the food and cocktails are delicious, you’re really going here for the ambiance.
This restaurant is built inside an abandoned theater. In the enormous dining room, you’ll find intricate murals on the walls, chandeliers hanging from the high ceilings, and gold trimming everywhere you look. It’s a picture of grandeur!
Boston Common and Boston Public Garden
After you’re done dining, head over to the nearby Boston Common and Boston Public Garden. Despite being directly next to each other, these public areas have their own unique personality and features. They’re also best to visit at different times of the year.
The best time of year to visit the Boston Public Garden is during the spring and summer, when you can spend the day strolling around the flowers or taking a tour of the lake on the famous Swan Boats. But the best time to visit the Boston Common is late in the year when the Frog Pond becomes an ice-skating rink and the park is illuminated with hundreds of twinkling lights. But no matter when you visit, be sure to take a ride on the Boston Common’s carousel and say hello to the “Make Way for Ducklings” bronze statues in the Boston Public Garden.
Omni Parker House (and The Last Hurrah)
When you’re ready for dinner, venture over to the Omni Parker House, a historic hotel that also happens to be the home of the Boston Cream Pie. While the main restaurant, Parker’s Restaurant, is only open for breakfast and lunch, you can grab dinner and a drink at the hotel’s whiskey bar, The Last Hurrah.
And don’t worry – you can get a Boston Cream Pie for dessert at the bar. You can also get a Boston Cream Pie in cocktail form if you just can’t get enough of Boston’s famous treat!
Boston’s Theater District
End your night by taking in a show in Boston’s Theater District. You have plenty of options for seeing a live production in this area of Boston, but keep in mind that you may need to buy tickets in advance, depending on what you’d like to see.
The Boston Opera House is a beautifully ornate theater where you can see spectacular productions of touring Broadway shows. Although you should most likely get tickets ahead of time to see one of these shows, some performances also have lotteries. If your name gets picked for a lottery, you’ll get discounted tickets for the show that day.
At the Colonial Theatre, owned by Emerson College, you can often see shows before they premiere on Broadway at much less expensive rates. The Wang Theatre was designed to look like the Paris Opera House, so it’s the picture of opulence. Here you’ll find touring comedians, singers, and much more. No matter which theater you head to, you are in for a night filled with world-class entertainment.
Boston Weekend Itinerary – Day 2
For the second day of your 3-day trip to Boston, you’ll start at the Boston Public Market. This year-round indoor market offers artisanal treats from local New England vendors. Here you’ll find 30 artists, bakers, butchers, and so much more selling seasonal, locally-sourced items.
Bagel
For your breakfast on the second day of your 3 days in Boston, take a walk around the market and pick out your favorites. Grab a bagel from the Bagel Guild, make a crepe at the Bon Appetit Creperie, or treat yourself to a Boston Cream Donut at Union Square Donuts.
Boston Cream Donut
For a drink, order a latte at George Howell Coffee or grab some green juice at Mother Juice. When you’re done eating, take a walk around the market and see what else you may want to pick up. There’s plenty to explore here, from stonework to allergen-friendly truffles.
Faneuil Hall Marketplace
Next up, you’ll head to nearby Faneuil Hall, a historic area that has served as a meeting hall and marketplace for more than 270 years. Walk the cobblestone street and take in the history of this cultural hub. Take a stroll through the Faneuil Hall Marketplace, also known as Quincy Market, to discover tons of shops, restaurants, and stalls.
From shops with handmade Christmas ornaments to comic book stores, there’s something for everyone at this fun location. When you’re ready for lunch, you have many options here, but if you want an iconic Boston treat, get a bread bowl of clam chowder from the Boston Chowda Co.
Boston Chowda Co
From Faneuil Hall, take a walk over to the Boston Harbor, where you’ll find the next item on your Boston itinerary. What you do next will depend on the seasons. If you’re visiting in spring, summer, or early fall, hop aboard one of Boston’s famous Duck Tours.
Duck Tours
These tours launch from three locations, one of which is near the New England Aquarium. A colorful cast of characters called the ConDUCKtors will take you aboard a DUCK, an authentic World War II amphibious vehicle.
On your tour, you’ll see landmarks of all kinds, from the Old State House to the iconic “Cheers” pub, while the ConDUCKtors tell you little-known facts about these locations. But since you’re in an amphibious vehicle, the big treat of this tour is that you’ll splash down in the Charles River, where you’ll get an incredible view of the Boston skyline.
New England Aquarium
However, due to Boston’s climate, the Duck Tours don’t run from late November to early spring. If that’s when you’re visiting for your long weekend in Boston, you should instead explore the Boston Harbor and head to the New England Aquarium.
This aquarium, which is dedicated to conservation and using innovative solutions to solve threats to ocean life, is the perfect spot for an afternoon of fun and education. From the busy and vibrant Indo-Pacific Coral Reef exhibit to the many penguins of the Penguin Colony exhibit, it’s easy to spend a whole day watching these majestic creatures.
Union Oyster House
When you’re done with your tour or your day at the aquarium, it’s time to head to dinner. And there’s perhaps no more iconic dinner spot than the Union Oyster House. This seafood restaurant is not only Boston’s oldest restaurant, but it’s one of the oldest restaurants in the United States!
Dating back to 1826, this National Historic Landmark has maintained its original style after all these years. Dining at this little piece of history is always a delight. Because this landmark is so famous, it’s often busy on weekends, so be sure to reserve a table in advance.
Dessert at the Union Oyster House may be delicious, but we recommend going on a little walk to the North End to take part in the “Great Cannoli Debate.” Some say the best cannoli can be found at Mike’s Pastry. Others say it’s at Modern Pastry. As for us, we like Bova’s Bakery. So sample your way around the North End and pick which cannoli you think ranks the best.
Boston Weekend Itinerary – Day 3
Newbury Street
For the last day of your 3 days in Boston, you’re going to want to start over on Newbury Street for one of our favorite Boston brunch spots, Trident Booksellers & Cafe. If you’re a book lover, you’ll fall in love with this place, which serves up breakfast favorites inside an indie bookstore.
Put your name down for a table and then wander your way around the shop, searching for your next great read. Then, when the table’s ready, order off their massive menu, filled with seasonal treats. Although you can’t go wrong with anything on the menu, we love the Lemon Ricotta Stuffed French Toast, made with thickly sliced challah bread.
Then, head out onto Newbury Street for some shopping. Newbury Street is famous for its restaurants, boutiques, and one-of-a-kind stores. For magical trinkets and a little bit of pixie dust, visit the famous Fairy Shop.
And for handmade chocolates like you’ve never seen before (including in the adorable shape of penguins), stop by L.A. Burdick Handmade Chocolates. If you’re an art lover, you’ll also find plenty of art galleries dotting this street.
Trinity Church and Old South Church
From Newbury Street, take a walk over to Copley Square, a famous public square in the Back Bay neighborhood. Take in the art and architecture of this historical area. Here you’ll find the stained glass-filled Trinity Church, the enchanting green-domed Old South Church, and the massive Boston Public Library. Take some time exploring these landmarks, as the interiors are just as incredible as the facades.
Boston Public Library
For lunch, visit nearby Saltie Girl, which serves up one of the best versions of a New England classic: the lobster roll. This Boston favorite is often busy, especially on weekends, so you may want to make a reservation for lunch. If you’re traveling with seafood lovers, be sure to order a Seafood Tower, which is filled with plenty of sustainably-caught seafood options.
From there, it’s time to hop aboard the T and head to Fenway Park. No matter what time of year you visit for your long weekend in Boston, you should spend some time over in the Fenway area. If you’re a baseball fan, definitely look for tickets for a game at this historic location. Fenway is unlike any other baseball field. There’s history in every seat!
Fenway Park
One thing to note, however, is that you may want to skip visiting Copley Square if you’re going to a game. The T is often crowded on game days, and it may take longer to get to Fenway than you’d expect. So, it’s worth heading over to Fenway a little early. If you arrive long before the game starts, don’t fret. You can always spend some time walking the Jersey Street pedestrian mall, formerly known as Yawkey Way.
If your 3-day trip to Boston isn’t during baseball season, you should still pay Fenway a visit. You can take a tour of the park, or you can check out what events are happening in the stadium. The park does a concert series every summer, so you may just see your favorite performer at this iconic field.
Finish off the night and your long weekend in Boston with dinner and drinks at the Bleacher Bar. This unique bar is actually beneath Fenway Park’s bleachers and offers you a view of centerfield. Even if there’s no game happening, you’ll love taking in the sights of Fenway from this famous bar. Grab yourself a drink and a Bleacher Burger, and enjoy dining at this historic park!
More Places to Eat & Drink in Boston
Try an award-winning doughnut at Blackbird Doughnuts:
This Boston staple started in the South End, but you’ll now find them at their flagship location, as well as in three other Boston locations: Fenway, Beacon Hill, and the Financial District. For a truly unique doughnut, try the Everything Bagel, a brioche doughnut with cream cheese filling topped with everything bagel spice.
Venture over to Cambridge for the famous Mr. Bartley’s Burger Cottage, a Harvard Square institution since 1960:
Known for its massive burgers and legendary frappes, this place is comfort food to the max. We love The Yoda, a burger topped with pesto mac and cheese.
Grab a slice at Regina Pizzeria:
This North End staple has been serving up some of the best pizza in Boston since 1926. This pizzeria boasts a massive menu, but we think the traditional Cheese Pizza is still the way to go.
What to do if you have more than 3 days in Boston
Meet your favorite authors at the Boston Book Festival:
Happening every October in Copley Square, the Boston Book Festival invites the best authors around to partake in a weekend filled with literary events. Past speakers include Lemony Snicket, Rick Riordan, and Margaret Atwood. These conversations and events happen throughout Copley Square, so you’ll get to be inside beautiful locations like the Trinity Church while you listen to your favorite writers talk about their craft.
Take a Freedom Trail tour:
The Freedom Trail is not to be missed if you’re a history lover. This walking tour takes you to 16 historical locations that were important to the Revolutionary War, like the Paul Revere House and the Old South Meeting House. While you could walk this trail by yourself, you also have several options for guided tours, complete with a tour guide dressed in period garb.
Board the trolley for the Ghosts & Gravestones Tour:
For a different side of Boston’s history, this nighttime tour will show you the haunted parts of this historic city. On this Trolley of Terror, you’ll be led through tales of the not-so-happy haunts of the Omni Parker House, the biggest grave-robbing scandal ever to hit New England, and much more.
See a show at the Brattle Theatre:
If you’re a movie lover, you should head to this historic Cambridge movie house, known for its stunning architecture and special event screenings. There’s something new playing on the one screen here each night, from new award winners to classic favorites, so be sure to check the website to see what’s being shown.
Stroll through the Isabella Stewart Gardner Museum:
This art museum is a Venetian palace surrounded by lush greenery, housing incredible American, Asian, and European art. It’s a remarkable place to spend an afternoon and one of the best museums to be found in Boston.
We hope you enjoy your weekend trip to Boston! Should we add something else to our 3-day Boston itinerary? Let us know in the comments.
Planning a trip to Massachusetts? Check out our favorite travel guides and resources!
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