3 Day Itinerary for Boston

Boston, Massachusetts’s capital city, is known for its famous clam chowder, baseball (Red Soz), Fenway Park, and baked beans. The city is also known for its rich history, often referred to as the “Cradle of Liberty” due to its significant role in the American Revolution.

To organize a 3 Day itinerary for Boston, consider visiting the Freedom Trail, the iconic Massachusetts State House, the Paul Revere House, and the Old North Church. Visit the Museum of Fine Arts and the Irish Heritage Trail for unique experiences. Indulge in the passionate sports culture, with several famous sports teams during the primary league season.

Culinary delights in Boston include classic New England clam chowder and Boston cream pie. When planning your trip, consider visiting during spring or summer when temperatures are mild and the atmosphere is bustling. For accommodations, consider staying in Downtown Boston or Beacon Hill, especially for first-time visitors.

Indulge in top attractions and experiences during your 3 Day trip to Boston, including exploring historical landmarks, strolling along picturesque streets, and indulging in local cuisine.

Overview of 3 Days in Boston Itinerary

Here’s a glance at what you’ll see and do in three days in Boston:

Day 1 in Boston

• Explore the Freedom Trail 
• Brunch at Polcari’s Coffee
• Finish the Freedom Trail Tour 
• Get Dessert at Blackbird Doughnuts
• Visit the Fenway Park 
• Discover Boston’s Beer Breweries

Day 2 in Boston

• Breakfast Picnic at Boston Public Garden
• Discover art at the Isabella Stewart Gardner Museum
• Visit the Museum of Fine Arts 
• Snacks at Boston’s Time Out Market
• Shop at Faneuil Hall Marketplace
• Spend your evening at Newbury Street

Day 3 in Boston

• Explore the Harvard University 
• Lunch at a Cambridge Restaurant
• Visit the New England Aquarium
• Climb up and Have dinner at the Skywalk Observatory

Day 1 in Boston

Explore the Freedom Trail 

When visiting Boston, seeing and exploring the Freedom Trail is a must; and what better way to start your 3 days in Boston than to complete this trail tour? 

The Freedom Trail has been an iconic destination in Boston because of its historical heritage. This 4-kilometre (2.5 mile) historic path will take you through the city’s most important sites. 

While you can always book a guided trail tour, you can also do this independently (especially with a detailed itinerary) since there are plenty of informative signs inside the trail. 

The best spot to begin your trail tour is at the Boston Common, this is the oldest public park in the entire United States. As you walk further, you will also pass by the Massachusetts State House, which is the seat of the state government. 

Top Pick

From Lobster Tail to Freedom Trail

• 5 hours 
• Local Guide
• Food & History tour

Check Price

Continue the trail and admire the Park Street Church and the Granary Burial Ground before reaching the King’s Chapel. Next to these is the courtyard of the Old City Hall, where the Benjamin Franklin statue stands. 

Although it may look like a lot, you can always finish half the trail and return after lunch since you can enter anytime. But I suggest you go through a few more before you fuel up. 

As you pass the Old City Hall, the trail will take you to the Old Corner Bookstore, Old South Meeting House and Old State House.

You don’t necessarily need to enter all of these since there are too many, but major attractions like the Old State House will be worth seeing. Before exiting, you can end your morning trail tour by visiting the Boston Massacre Site. 

Brunch at Polcari’s Coffee

At this point, you’re probably hungry (and thirsty) from all the walking you did. For a delightful culinary experience, head to one of Boston’s most iconic cafes – Polcari’s Coffee. The cafe has been in operation for more than 100 years already, serving classic Italian delicacies and dishes. 

This beloved family-owned cafe serves delicious brunch dishes. You can indulge in their mouthwatering pancakes, omelettes, or classic breakfast sandwiches with their signature Italian coffee.

Moreover, the cosy ambience and friendly service make Polcari’s Coffee a perfect spot to start your day in Boston. After having a hearty meal, you can get a drink and bring it with you as you stroll along the Freedom Trail (for the second half). 

Finish the Freedom Trail Tour 

While you can always go to another place after seeing the trail in the morning, finishing off is highly suggested, especially since you haven’t seen some of the notable attractions inside. 

For the second part of your trail tour, start at the Faneuil Hall Marketplace, home to modern-day Quincy Market and known to many as the Cradle of Liberty.  This continues to be one of the most critical spots in the trail and the whole of Boston. 

After checking out the Faneuil Hall, continue to the other side of the trail, starting at Paul Revere House. This is Boston’s oldest surviving clapboard frame house and was turned into a museum. 

As you go on, you will also pass by the famous Old North Church, Copp’s Hill Burying Ground and the Bunker Hill Monument. As mentioned earlier, you don’t have to enter all these; instead, you can admire them as you walk through the trail (but if you have more time, it’s recommended to at least enter the sites for a few minutes). 

The last stop for your freedom trail tour will be the U.S.S Constitution, also called the Old Ironsides. This is the oldest commissioned warship in the world and is docked in Charlestown. 

Completing the Freedom Trail will leave you with a deep appreciation for Boston’s role in American history.

Get Dessert at Blackbird Doughnuts 

A day without dessert will never be complete, and while in Boston, you should have the local’s (and visitors’) favourite sweet treat. Blackbird Doughnuts is a famous place in Boston that serves sweet (and savoury) doughnuts and more. 

This is a staple breakfast place for those in a rush, which means you might miss out on their best flavours in the afternoon. Still, you can always indulge in their best-selling Donut ice cream sandwich. They even sell Boston’s famous warm chocolate cookies, which they serve till 3 AM. 

Visit the Fenway Park 

You might be that person who is planning to go to Boston because of your favourite team. But if not, it is still a must that you visit the Fenway Park. The Fenway Park is the oldest Major League Baseball stadium in the United States. 

If you are a sports enthusiast, plan your trip to catch a Boston Red Sox game during the game season. But if time does not permit, you can still take a guided tour of the ballpark to learn about its storied history. 

Top Pick

Historic Fenway Park tour

• 1 hour
• Professional Guide
• Access to Museum

Check Price

The tour will let you explore the famous “Green Monster” left-field wall, soak in the atmosphere of this legendary venue, and appreciate the Bostonians’ passion for their beloved team. You can take many photos here and return soon when a game shows up! 

Discover Boston’s Beer Breweries

Since Boston takes pride in having a strong Irish influence, the city is known for their thriving craft beer scene. So, beer enthusiasts should make it a point to explore the city’s breweries. 

Boston is home to several pubs and beer breweries, so you can have a separate tour to see all the famous breweries in the city and learn about the process of creating excellent craft beer. 

If you decide to book a tour, you will visit The Harpoon Brewery, one of the city’s oldest breweries. You’ll just need to book in advance a ticket to enter since they sell out fast every day. 

Inside, you can sample their diverse selection of beers or watch others do it (if you don’t feel like drinking). After the tour here, you can return and enjoy your dinner at one of Boston’s most famous (and fancy) restaurants, Bistro du Midi.

Day 2 in Boston

Breakfast Picnic at Boston Public Garden

On your second day in Boston, why not start with a delightful breakfast picnic at one of the city’s most beautiful spots – the Boston Public Garden? This is a serene oasis in the city’s heart where you can enjoy any time of the day. 

But, for this itinerary, we suggest you visit there early to have the place to yourself (almost) and enjoy the famous Victorian-era garden during your trip. 

On the way, grab some pastries and coffee from a local bakery for your “picnic” food. The garden is so vast that you can easily find a cosy spot to enjoy your meal amidst the beautiful landscapes, blooming flowers, and iconic Swan Boats. 

After taking in the atmosphere and finishing your food, you can also stroll around the park, admire the charming Victorian-era statues, or even take a 15-minute Swan Boat to ride in the lagoon. 

Discover art at the Isabella Stewart Gardner Museum.

As we’ve mentioned earlier, Boston is known for its historical heritage and rampant culture and arts, which is why going on a Museum tour is a must for your second day in the city! 

The first museum you can visit is the Isabella Stewart Gardner Museum of Art. This is one of the best museums in Boston, housed in a Venetian-style palace. 

Isabella Stewart Gardner showcases a diverse collection of artwork spanning different periods and cultures. Explore the three floors that are meticulously curated galleries filled with paintings, sculptures, tapestries, and decorative arts. 

Also, get to admire masterpieces by renowned artists like Rembrandt, Vermeer, and Titian and be captivated by the museum’s enchanting courtyard garden, which adds to the unique ambience of this cultural gem. 

Visit the Museum of Fine Arts 

Another favourite and world-renowned museum, especially for art enthusiasts, is the Museum of Fine Arts. It is one of the most comprehensive art museums in the world, housing over 500,000 works of art. 

When visiting the museum, you’ll see an exploration of human creativity across different cultures and periods. Start by marvelling at ancient Egyptian artefacts and European masterpieces to check out Asian art and contemporary installations.  

This gives you enough reason to take advantage of the Museum of Fine Arts, especially if you stay for 72 hours in Boston. You can directly get your ticket from the museum upon arrival.

It’s also suggested to check the museum’s schedule beforehand since they also host special exhibitions and events, providing a dynamic and engaging experience for visitors of all ages.

Snacks at Boston’s Time Out Market

After visiting two of Boston’s famous museums, why not enjoy a treat at Boston’s Time Out Market in the vibrant Fenway neighbourhood? 

The Time Out Market in Boston just opened a few years back, and since then, it has been a favourite go-to place for residents and visitors alike. Here you can find several gastronomic delights with distinct and unique flavour experiences. 

Featuring around 15 eateries headed by Boston’s top restaurants and chefs, you’ll find a snack fitting your taste and preference.

Plus, with the place’s modern and trendy atmosphere, you’ll surely enjoy your time savouring the city’s flavours while enjoying the lively atmosphere of this bustling food hall.

Shop at Faneuil Hall Marketplace

For a dose of shopping and entertainment, make your way to Faneuil Hall Marketplace. This historic marketplace is the perfect afternoon destination where you can shop. 

Although you might have passed the area already during your Freedom Trail, this time will differ. 

Faneuil Hall marketplace has been a bustling hub since the 18th century and continues to be a vibrant destination for locals and visitors alike. It is home to several boutiques and shops where you can shop for unique souvenirs, fashion, jewellery, and artisanal goods. 

Moreover, catch a glimpse of the famous Quincy Market, where you can sample delicious local food or enjoy live music.

Spend your evening at Newbury Street

As the day winds down, spend your evening at one of Boston’s famous shopping and entertainment districts. 

Newbury Street is an iconic street in Boston’s Back Bay neighbourhood, renowned for its upscale boutiques, trendy shops, art galleries, high-end restaurants and stylish cafes. This will be a paradise if you want to continue shopping, especially in high-end boutiques. 

The street is also home to numerous art galleries that showcase a diverse array of contemporary and traditional artwork. You can stroll and appreciate the talent and creativity on display before you get your dinner fix. 

Since Newbury is dotted with various restaurants and cafes, you can find something that suits your palate. Meanwhile, if you want a drink to cap off your night, try out Earls Kitchen + Bar. 

Day 3 in Boston

Explore the Harvard University 

Every visit to Boston is complete with exploring the prestigious Harvard University. For your third and last morning in Boston, visit the other side of the city and hop on a bus going to Cambridge. No worries because this is just a few minutes from the centre of Boston. 

Once the U-Shaped Harvard Stadium comes into view, you know you’re already near! Just switch over to the other side of the Charles River, and soon you will arrive at Harvard Square. 

While you can do a tour inside the campus on your own, you can also book a tour that will take you around the university. Some places you can check out inside are the beautiful architecture of buildings like Memorial Hall and Widener Library. 

Top Pick

Harvard Campus Tour

• 1 hr 10 mins
• Student-Led Tours

Check Price

The essence of seeing the university up close is to see the college life of those enrolled in the University and, simultaneously, discover a few fascinating exhibits inside the campus. 

Some museums and galleries worth visiting are the Harvard Museum of Natural History to discover fascinating exhibits on dinosaurs, gems, and minerals; the Harvard Art Museum for luminaries; and the Peabody Museum of Archaeology. 

Lunch at a Cambridge Restaurant

After a morning of exploring the world’s top university, you deserve a treat from one of Cambridge’s best restaurants. Regardless of who you ask, you will be brought to Harvard Square, a legendary area for students to get food. 

Harvard Square is home to many restaurants and coffee shops, which you can also choose from. This time, we suggest you visit this 40-year-old restaurant called Harvest. 

Harvest is a farm-to-table restaurant that uses locally sourced ingredients and creates them into an elegant seasonal menu. They focus on Contemporary American dishes, which is a must in Boston. 

Visit the New England Aquarium

A trip to Boston will only be complete if you check out one of the city’s famous interactive galleries or museums. After your morning tour in Cambridge, return to Boston and go straight to the New England Aquarium. 

New England Aquarium has become a famous destination ever since it made its way through and became a catalyst for global change in the country. Their commitment to marine animal conservation and innovative scientific research has helped reach effective advocacy for ocean life. 

When visiting the Aquarium, you can explore its exhibits that house a variety of aquatic creatures, including penguins, sea turtles, sharks, and colourful tropical fish. They also have an incredible Giant Ocean Tank where you can watch divers interact with a vibrant coral reef ecosystem. 

Climb up and Have Dinner at the Skywalk Observatory

Before ending your three-day trip in Boston, get ready to take in breathtaking views of Boston’s skyline at the Skywalk Observatory at the Prudential Center. 

The Skywalk Observatory offers a 360-degree view of Boston from its highest floor at 222 metres tall. Take a high-speed elevator to the 50th floor, and there you will be greeted with panoramic vistas of the city and its surroundings. 

You can see landmarks like Fenway Park, the Charles River, and the historic Back Bay neighbourhood from this vantage point. By this time, you’ll see the sunset over the city skyline and enjoy a nice night city view. 

Afterwards, you can continue enjoying the view from above while having dinner at the building’s restaurant.

Tours in Boston

Tasting Food Tour 

Not known to many, Boston has many diverse gastronomic delights. This is why; if you are going to Boston and have spare time, we suggest you book a Walking Tasting Food Tour in the city. 

You will be led by a professional tour guide who will bring you to some of the city’s best local restaurants during the tour.

Get to sample Boston’s most delicious bites while getting first-hand information about the town and its culinary history. 

Some of the food you can taste are the famous Boston clam chowder, lobster rolls, cannoli, and a secret dish you will share during the tour. 

Sunset Cruise

Another great tour you can include in your three days in Boston is the Sunset Cruise. This is an excellent alternative to sunset sightseeing in this itinerary, especially if you want to admire Boston from the waterfront. 

During the tour, you will pass by the Old North Church, the Charlestown Navy Yard, Leonard P. Zakim Bunker Hill Memorial Bridge, and the USS Cassin Young.

The cruise includes alcoholic beverages, soda and snacks that you can enjoy on the open-air deck or interior cabin.

3-Day Itinerary for Boston Wrap-up

We hope this article has helped you plan your 3 Day Itinerary trip to Boston. Now that you have an idea of things to do, what to visit and even where to eat in the city, you’re surely ready to conquer Boston! 

Recommended tours in Boston

• Boston half day private driving tour
• From Lobster Tail to Freedom Trail
• The Best of Boston: Private Half-Day Highlights Driving Tour
• Full-Day Private Tour of Boston with Pick Up
• Tour of Boston’s Revolutionary and Drunken Past
• Small Group Boston Freedom Trail History Walking Tour
• Sunset Sailing Cruise on a Tall Ship in Boston Harbor
• Boston Harbor Sunset Cruise
• The Revolutionary Story Walking Tour in Boston
• Boston’s North End Pizza & History Walking Food Tour
• Underground Donut Tour – Boston Historic Downtown Tour
• Harvard University Campus Guided Walking Tour
• Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River
• Tour of Historic Fenway Park, America’s Most Beloved Ballpark

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