Since its founding in 1630, Boston has stood as a City on a Hill — the perfect place for visitors in search of culture, history, and unforgettable times. Whether you want to explore the world of America’s Founding Fathers, check out high-end fashion boutiques, or sit down for a dinner of authentic New England seafood while breathing in the refreshing Atlantic Ocean air, Boston has something for every traveler.

Here’s our 48-hour itinerary for globetrotters looking to get acquainted with Boston, a step-by-step tour that introduces visitors to some of Beantown’s most iconic landmarks and world-renowned destinations.

Day 1 in Boston

9:00 a.m.

Start your Boston adventure in the North End, the city’s oldest residential community, which dates back to the 1630s. Located on Boston’s beautiful waterfront, the North End has been a beacon of hope and opportunity for Bostonians for centuries. The North End was an important gathering spot for patriotic Sons of Liberty in Revolutionary times. And, it was also the destination for many immigrants fleeing persecution and looking for a better life in the United States in the late 1800s.

Now known as Boston’s Little Italy, the North End is home to dozens of outstanding Italian bakeries and cafes. Before heading out, enjoy a breakfast of freshly baked pastries and a cappuccino at Modern Pastry Shop, a local favorite for an authentic Italian start to your day. The Modern, family-owned and operated since 1930, has been the recipient of countless awards in its decades of treating Bostonians to the best in Italian cooking. Regulars are particularly fond of the bakery’s cannoli, but their lobster tails are also big crowd-pleasers.

10:30 a.m.

Step back in time and take a walk along the Freedom Trail, a 2.5-mile route marked by a red line embedded in the sidewalk that leads you to 16 historically significant sites. You’ll visit Paul Revere’s House, the Old North Church, and the Massachusetts State House along the way. History lovers will get an abounding sense of Americana as they follow in the footsteps of the earliest patriots. First-time guests will particularly enjoy stopping at the Bunker Hill Monument. This location honors the veterans of one of the Revolution’s first battles and provides exceptional views of Beantown’s skyline.

Another popular stop on the Freedom Trail is the USS Constitution. the oldest commissioned warship in the world. Better known as Old Ironsides, the Constitution was launched in 1797 and saw action in the War of 1812 before being converted into a museum ship. Now committed to telling the story of the U.S. Navy’s earliest days, tours of the Constitution take visitors back in time to America’s idealistic revolutionary self.

12:30 p.m.

After a morning of exploration, head to Quincy Market, a bustling marketplace adjacent to Faneuil Hall. Known as the Cradle of Liberty, Faneuil Hall was one of the spots where Boston patriots articulated their grievances against the British Crown. They spearheaded the cry “No Taxation Without Representation!” across the 13 colonies.

The historic Quincy Market, a historic marketplace dating from 1826, encompasses three buildings that offer a wide array of food vendors serving everything from New England clam chowder to international dishes. The market is also a haven for many lively street performers, including musicians and actors dressed in colonial attire. It’s the perfect spot for a quick and satisfying lunch with fun entertainment.

2:00 p.m.

Take a leisurely stroll through the Boston Common, America’s oldest public park. (Oh, and a helpful tip: it’s the “Boston Common,” not the “Boston Commons.” There’s no quicker way to reveal yourself as a tourist than to fall into this common faux pas.) Among the most popular attractions in the Common is the Frog Pond Carousel, a charming ride built in 1947 by the famed designer Allan Herschell. Also of note is the Robert Guild Shaw and the 54th Massachusetts Regiment Memorial, a stunning bronze sculpture honoring the sacrifices of the first Black soldiers to fight in the Civil War.

Adjacent to the Common is the Boston Public Garden was the first public botanical garden in the United States. The Public Garden is an urban oasis in the very heart of Boston. Along with the beauty found in each and every tulip and cherry tree that calls the garden home, the grounds of the Public Garden also have many fun activities for guests. Of course, no visit to the Public Garden would be complete without a ride on the famous Swan Boats around the garden’s lagoon. Calming and peaceful, the Swan Boat rides are open from April to September. And, they’re among the best ways to experience the Boston Public Garden’s lush surroundings.

4:00 p.m.

Spend the afternoon at the Museum of Fine Arts, one of the largest and most comprehensive museums in the United States, with a new wing focusing on American art. The museum also features an impressive collection of ancient Egyptian artifacts, and European paintings, including works by Van Gogh, Gaugin, Rembrandt, and one of the largest collections of the works of Claude Monet in the world. With over 450,000 paintings, sculptures, and other masterpieces, the MFA is a paradise for visitors to Boston with a love for art and culture.

7:00 p.m.

For dinner, venture to the South End, known for its Victorian brownstone buildings and vibrant dining scene. The neighborhood prides itself on its eclectic mix of the old and the new, welcoming visitors with historic homes and modern amenities. One of the best spots in the city to enjoy a simple walk before dinner is along Tremont Street. The array of trendy eateries offers everything from farm-to-table American cuisine to global dishes. Diehard foodies will fall in love with the Edomae-style sushi found at 311 Omakse. Other options include the Barcelona Wine Bar‘s extensive tapas and wine selection, Toro‘s authentic Spanish cuisine, and Myers + Chang‘s innovative Asian fusion dishes.

9:00 p.m.

End your day with a relaxing walk along the Charles River Esplanade, enjoying the city lights and the tranquil river view. Along with the exceptional views of Boston bathed in the darkness of the night sky, evening concerts are a regular fixture of the Hatch Shell, the Charles River Esplanade’s free music venue. The Hatch Shell welcomes a variety of different performers, from classical orchestras to rock bands to pop singers. But it’s perhaps best known for hosting the Boston Pops’ annual Fourth of July concert.

Day 2 in Boston

9:00 a.m.

Start your second day with breakfast in the charming neighborhood of Beacon Hill, one of the oldest neighborhoods in the city known for its narrow, gas-lit streets, and brick sidewalks. Walk down Beacon Hill’s cobblestone paths, where Samuel Adams and John Hancock once passed. Enjoy the view of the stately Federal-style brownstones along the way.

Begin your morning in Beacon Hill at The Paramount, a neighborhood favorite since 1937, where the bustling atmosphere is as invigorating as the coffee. Known for its no-frills, diner-style breakfast, The Paramount serves up everything from fluffy pancakes to savory omelets, all cooked to order in an open kitchen. Another option is 75 Chestnut, where guests can enjoy traditional American breakfasts and a variety of comfort foods in a warmly decorated, inviting space.

Take a short subway ride to Cambridge and explore the prestigious campuses of Harvard University and MIT. Both offer public tours that provide insights into the history and culture of these renowned institutions.

Among the most frequented spots for guests visiting Harvard is Harvard Yard. Boasting over 22 acres, Harvard Yard is the oldest section of the university’s campus and is home to several of the school’s most iconic landmarks. In addition to the resting place of the statue of the school’s founder, John Harvard, Harvard Yard is also home to several of the school’s libraries and Memorial Church, one of the most beautiful buildings on campus.

Meanwhile, guests of the Massachusetts Institute of Technology flock to Killian Court, the location of the university’s commencement and the site of a range of awe-inspiring architecture. Killian Court is dominated by the Great Dome, an 8,800-foot dome that rivals the U.S. Capitol Building in size.

12:30 p.m.

After exploring Harvard or MIT, head to Central Square where you can find eclectic food options reflecting the area’s diverse community. From artisanal sandwiches to ethnic cuisines, there’s something to satisfy every palate. Roxy’s Grilled Cheese and Burgers is one of the biggest hits among visitors to Central Square. Once a simple food truck, Roxy’s now serves creative takes on regional favorites like The Central, a grilled cheese sandwich stuffed with roasted cremini mushrooms and sundried tomatoes. La Fabrica Central is also a popular dining spot, known for its expansive menu of Spanish and Caribbean cuisine.

2:00 p.m.

Spend your afternoon at the Isabella Stewart Gardner Museum. The iconic building is styled after a 15th-century Venetian palace. The museum showcases an exquisite collection of European, Asian, and American art in a unique and intimate setting. One of the most remarkable areas of the museum is the cloisters. The rooms on the ground floor are dominated by architecture and sculptures from medieval monasteries from all over Europe. The Spanish Cloisters are home to John Singer Sargent’s stunning fresco entitled El Jaleo, the museum’s most prized piece of artwork.

Before you head out, make sure to snap some photos of the floral displays found in the courtyard. During her life, Isabella Stewart Gardner had a deep affection for flowering plants. This love of all things floral is honored in the seasonal flower arrangements that welcome visitors to the courtyard.

5:00 p.m.

Head to the Back Bay area for some shopping on Newbury Street. This area is known for its mix of high-end boutiques and art galleries. Fashion enthusiasts will marvel at the sheer number of designer boutiques that call Newbury Street home. Ralph Lauren, Burberry, Chanel, and countless other titans in the world of high fashion have all set up shop on Newbury Street. There are shops all along Newbury Street, but you’ll find the higher end boutiques closer to the Public Garden, and the more eclectic and funky shops closer to Massachusetts Avenue.

Once you’ve shopped till you’ve dropped, take a break and enjoy a coffee or a sweet treat at one of Back Bay’s many cafes. Thinking Cup is especially highly regarded in the area. They pride themselves on only using the finest coffee beans and employing a team of knowledgeable baristas.

7:30 p.m.

Conclude your Boston visit with dinner at one of the many renowned restaurants in Back Bay. One great option is Sonsie, which impresses with its vibrant atmosphere and a diverse menu featuring global influences, making it a favorite along Newbury Street for both its lively bar scene and elegant dining. Stephanie’s on Newbury offers a sophisticated yet comfortable ambiance, perfect for enjoying upscale comfort food while people-watching from its popular sidewalk seating area. On the higher end is Grill 23 & Bar, Beantown’s premier steakhouse, known for sizzling entrees and an award-winning wine list.

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9:00 p.m.

For a final breathtaking view of Boston, head to the Skywalk Observatory in the Prudential Center. The Skywalk Observatory lets you see up to 100 miles away from the observation deck. Enjoy the bird’s eye view of landmarks like Fenway Park and the Boston Common. Views from the top of the observatory pair well with the Prudential Center’s on-site museum. Explore Boston’s past and peer into the city’s plans for the future. Gazing 50-stories above, the panoramic views of the city skyline at night provide a perfect end to your Boston adventure.

FAQs:

Q: How can I get around Boston during my visit?
A: Boston offers a variety of transportation options including the subway, buses, taxis, and rideshare services. Also, keep in mind that Boston is considered one of the most walkable cities in the United States.

Q: When is one of the best times of year to visit Boston?
A: It’s recommended to visit Boston during the spring (April to June) or fall (September to November), when the weather is pleasant and the city hosts many outdoor events.

Q: Are there any special events or festivals in Boston I should know about?
A: Boston hosts various events throughout the year such as the Boston Marathon in April, the Boston Harborfest in July, and the Head of the Charles Regatta in October.

Q: What should I pack for my trip to Boston?
A: Pack comfortable walking shoes, weather-appropriate clothing (layers are key), sunscreen, and a reusable water bottle.

Q: Can I explore Boston on a budget?
A: Yes, many of Boston’s attractions offer free or discounted admission on certain days, and there are plenty of affordable dining options in the city.

Q: Is it necessary to book tickets in advance for attractions mentioned in the itinerary?
A: It’s advisable to book tickets in advance for popular attractions like the Museum of Fine Arts and the Isabella Stewart Gardner Museum to avoid long lines.

Did we leave any must-do activities in Boston off our list? Tell us in the comments below!