Ultimate 3 Day Boston Itinerary: What To See And Do

Planning a 3 day trip to Boston? This 3 day Boston itinerary is perfect for first-time visitors wanting to explore the vibrant neighborhoods, the amazing food scene, and the historic landmarks.

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Boston is the largest city and capital of Massachusetts. It is also one of the most walkable and historically rich cities in the United States. Boston has a perfect mix of old-world charm, with cobblestone streets and colonial landmarks, and modern charm, with vibrant neighborhoods.

Explore the best of this 3 day Boston itinerary with the ultimate must-see spots, stunning hidden gems, the best local experiences, the delicious food scene, the interesting history of the city, and so much more.

In this post, we will take you on the Freedom Trail, explore the popular markets, enjoy the New England Aquarium, enjoy the Harbor, explore the iconic Fenway Park, take a tour of Harvard and its amenities, walk along Beacon Hill, and so much more.

This post is all about the ultimate 3 day Boston itinerary.

Ultimate 3 Day Boston Itinerary

Day 1: History And Harbor Views In Downtown Boston

Boston Common And the Public Garden Of Boston

The best way to start this 3 day Boston itinerary is by taking a stroll through the Boston Common. The Boston Common is America’s oldest public park and is full of lush green gardens, lots of greenery, and trees. Check out the Boston Common Frog Pond, where you can also see the Massachusetts State House just across the street.

The Boston Common is also right next to the Public Garden, which is another stunning urban oasis, great for a walk. You could also take a ride on the iconic Swan Boats, this is a Boston tradition that has been around for many years. Check out the Duckling Statue and walk along the paths that are lined with stunning tulips, roses, and many other plants and flowers. Perfect way to start your itinerary.

Walk The Freedom Trail: Explore America’s Revolutionary Past

Next, walk along the Freedom Trail. This is a must-do on your 3 day Boston itinerary. This path is made of red bricks and is approximately 2.5 miles long, and takes you through 16 historic landmarks throughout the trail. These landmarks played a huge role in America’s journey to independence. You can do the walk on your own or do a guided tour as well for a more detailed explanation of the history of the Freedom Trail. You will see burial grounds, churches, battle sites, and so much more history. This is great for all the history buffs.

Explore the Quincy Market

You have to visit the famous Quincy Market when in Boston. The Quincy Market was built in the 1820s and is an iconic food hall that is full of energy and local charm. It is also a part of the Faneuil Hall Marketplace, which is a shopping and dining area in Boston. Some of the must-try foods at the Quincy Market include Lobster Rolls, New England Clam Chowder, Boston Cream Pie, Italian Cannoli, and lots of other seafood and sandwiches. Other than food, you can see street performers and boutique shops as well.

Visit The New England Aquarium

Another must-see attraction while in Boston is the New England Aquarium. The New England Aquarium is great for families, couples, and solo travelers, and is such a cool experience that is fun and educational. It is located right on the Boston waterfront and is home to thousands of marine animals like sharks, penguins, reefs, and more.

The top attractions within the museum include the Giant Ocean Tank, which is a Caribbean coral reef habitat that is filled with sea turtles, sharks, rays, and beautiful fish. The Penguin Colony is full of African and rockhopper penguins. The Shark and Ray Touch Tank, where you can touch and pet the animals in shallow waters. The Marine Mammals Center, which is full of sea lions and seals, allows you to watch them in their natural habitat. There is also an IMAX Theatre with documentaries and Whale Watching Tours available. Get tickets for the New England Aquarium here.

Take A Harbor Cruise

To finish off day 1 of your 3 day Boston itinerary, do a Boston Harbor Cruise. This offers a great view of the Boston skyline and gives you a little break from walking around all day. While you are on the Boston Harbor Cruise, you can check out some historic landmarks, stunning neighborhoods, and islands as you cruise by.

There are a few different types of cruises as well. There is the Historic Sightseeing Cruise, where you will also see and learn about iconic Boston landmarks from the American Revolution, like the USS Constitution, Bunker Hill Monument, and the Boston Light, which was America’s first lighthouse. The Sunset Evening Cruise to see the skyline at sunset. Whale Watching Tours Cruise, which takes you on a 3-4 hour cruise that takes you to Stellwagen Bank, one of the best whale-watching spots in the world. Only seasonal, though. And an Island Hopping Ferry.

Day 2: Arts, Culture, And Academic Vibes

Copley Square And Newbury Street

Start day 2 of this 3 day Boston itinerary by heading to the Back Bay and checking out Copley Square and Newbury Street. Copley Square is located in the centre of Back Bay and is surrounded by many of Boston’s most iconic buildings. Check out the Boston Public Library, the Fairmont Copley Plaza Hotel, Trinity Church, and the Copley Square Farmers Market. Next, visit Newbury Street, which is known as Boston’s most fashionable street. It stretches over 8 blocks and has lots of luxury boutiques, trendy cafes, art galleries, restaurants, and more.

Tour Fenway Park

Fenway Park is a must-see when in Boston. Fenway Park is one of Boston’s most iconic landmarks and is home to the Boston Red Sox MLB baseball team. This is also the oldest MLB Baseball Stadium in the U.S. Fenway Park is worth a visit, whether you are catching a Red Sox Game or just visiting. There are Guided Stadium Tours where you can walk through the stadium and see the diamond up close, see the Green Monster seats, the press box, the dugout, and walk through the history of some of the most iconic MLB players, and so much more. This is such a cool and unique experience you have to do when visiting Boston.

Explore The Museum Of Fine Arts

Another great attraction in Boston is the Museum of Fine Arts, which holds a world-class collection of art and culture. This museum is one of the largest art museums in the United States, with over 500,000 pieces of art from all over the world. Some of the most popular exhibits include the Art of Ancient Egypt with mummies, tomb artifacts, and more. Stunning works of Art by Monet, Van Gogh, and more. The American Art Wing with iconic paintings and furniture from the modern and colonial eras. The Asian and Middle Eastern Collections with beautiful art, and so many more exhibits. Buy tickets to the Museum of Fine Arts here.

Dinner In The South End

To end day 2 of your 3 day Boston itinerary, grab some dinner in the South End. The South End is Boston’s trendiest neighborhood with the best food scene. There are so many different options, including unique restaurants, upscale dining spots, cute cafes, and so much more. There are so many unique menus to try while here, including seafood like lobster, lobster rolls, and clam chowder. Also, try some baked beans, which are popular here. Then, to finish off, make sure you try a Boston Cream pie or a Cannoli for dessert.

Day 3: Harvard, Some Hidden Gems, And The Beautiful Seaside

Cambridge And Harvard University

Start day 3 of this itinerary by heading over the Charles River to Cambridge and checking out the most famous Ivy League School in the U.S., Harvard University. Harvard University is also one of the oldest universities in the United States and is known for its academic excellence all over the world. Explore the Harvard Yard surrounded by student life and red-brick buildings. Enjoy the Harvard Art Museums with works of art by Monet, Van Gogh, and Picasso. Walk through the Harvard Museum of Natural History and the famous Glass Flowers exhibit, and so many more collections. You could also do a Guided Tour of Harvard to learn all the fascinating things about Harvard and its past.

Have Some Lunch In Harvard Square

Once you’ve explored Harvard and the Harvard Yard, head to Harvard Square for a break and some lunch. Harvard Square is packed with charming cafes, international eats, some local spots, and more. The best lunch spots in Harvard Square are Tatte Bakery & Cafe, Felipe’s Taqueria, Clover Food Lab, The Red House, Pinocchio’s Pizza & Subs, and Russell House Tavern, just to name a few.

Explore Beacon Hill And Acorn Street

Next, visit Boston’s most charming and picturesque neighborhood, Beacon Hill. Beacon Hill is a must-see area that is filled with beautiful sidewalks, row-style houses, lanterns, flower arrangements, 19th-century architecture, and more. This is what makes it one of the best spots to get some great photos. Beacon Hill is also one of Boston’s oldest neighborhoods, which is full of history and New England charm. A must-see street in Beacon Hill is Acorn Street, also one of the most photographed streets in the U.S. Acorn Street is a short, narrow street that is lined with cobblestones and perfectly preserved brick homes and beautiful flower boxes. A.K.A., why it is Instagram famous.

For more on fall getaways on the East Coast, check out the blog post “13 OF THE BEST FALL GETAWAYS EAST COAST YOU’LL LOVE“.

Walk Along The Charles River Esplanade

To finish off your 3 day Boston itinerary, take a relaxing walk along the Charles River Esplanade. This is a beautiful waterside park that is perfect for a quiet walk or even a riverside picnic. The Esplanade has stunning views of the Charles River, Cambridge, and Back Bay. Many people enjoy bike riding here or going for a run. Great spot to watch the rowers and sailboats during the summer months as well. Also, an amazing place to see the sunset.

For more on other places to explore on the East Coast, check out the blog post “THE ULTIMATE ROAD TRIP USA EAST COAST ITINERARY YOU’LL LOVE“.

Frequently Asked Questions (FAQs) About Boston

What is the best hop-on-hop-off tour? The best hop-on-hop-off tour is the “Boston Hop-On Hop-Off Trolley Tour with 13 Stops“. You can get a 1-2 day pass, and it stops at all the major attractions. The best way to see all of Boston.

Is 3 days enough for Boston? Yes, 3 days is plenty of time wot visit all the must-see attractions and even some hidden gems.

Best time to visit Boston? The best time to visit Boston is in the spring from April – June or fall from September – November. The weather is typically mild and less crowded than the peak season of summer, which is from July – August.

Other great tours? Another great tour that you could do would be the Boston Tea Party Tour. The best one is “Boston Tea Party Ships & Museum Admission“.

What To Pack For Boston? For packing tips, check out the blog posts “YOUR ULTIMATE SUMMER VACATION PACKING LIST YOU NEED“, “17 MUST-HAVE TRAVEL ESSENTIALS THAT ARE TOTAL GAME CHANGERS“, and “THE ULTIMATE LIST OF TRAVEL ACCESSORIES YOU NEED“.