3-Day Boston Itinerary for First-Time Visitors

Known for its predominantly Irish population, world and historical figures, and successful sports teams, Boston offers visitors a rich blend of history and culture, and a vibrant entertainment scene.

The city also has strong ties to Canada, which dates back to the founding of Halifax in 1749, when Boston businesses had an interest in the new settlement for shipping and fishing trade purposes.

The City of Boston is easily accessible by air, as it is well-served by direct flights from many major Canadian cities. For Canadians living in the eastern provinces, travelling by train or car is also a convenient option.

Planning a trip to Boston and want to know how to make the most of your visit in this historic and vibrant city? Here are our suggestions you can use to build a three-day itinerary, featuring some of its must-see highlights and attractions.

Start your day with a hearty breakfast at The Paramount, a cozy diner in the picturesque Beacon Hill area near Boston Common. The eatery is famous for its delicious pancakes, waffles and French toast.

After fueling up, explore Boston’s history and culture by joining a guided walking tour on the Freedom Trail. Along its 4km length, you will pass by 16 historical sites related to Boston's Revolutionary War, such as the Old State House, Faneuil Hall, Paul Revere House, and the Boston Massacre Site, among others.

Once you finish the tour, enjoy lunch and shopping at the 1800s Quincy Market. This historical marketplace has hundreds of vendors and eateries.

After lunch and some shopping, get on a Hop-On/Off sightseeing bus and explore other iconic places  such as the ‘Cheers! Bar’ and the Boston Tea Party Ships & Museum.

For dinner, we recommend heading to Boston’s Little Italy, in the North End neighbourhood. You will find great diner options serving everything from pizza to seafood. End the day with a dessert from one of the locally famous bakeries: Mike's Pastry or Modern Pastry.

After breakfast, start your day visiting the Skywalk Observatory (Prudential Centre) and enjoy breathtaking 360º views of Boston from the observation deck located on the 52nd floor. Also, take some time to learn more about the city's many landmarks and attractions, or chill on the open roof deck while enjoying your favorite beverage.

Next, stop by The Museum of Fine Arts, which is a short walk away. There you’ll find over 450,000 pieces of art spanning ancient to contemporary times. Some of the pieces include paintings by Monet, Picasso, and Van Gogh. After admiring the art collection, grab some lunch at one of the eateries located in the museum.

In the afternoon, head to the waterfront area near downtown Boston and board a cruise to see the city from a different perspective. Alternatively, you can go on a whale watching catamaran cruise tour. Adventure or adrenaline seekers looking for a thrill can ride a high-speed boat around Boston Harbour, which is available from May to October.

Back on shore, try Boston’s famous clam chowder, oysters or lobster rolls for dinner at one of the many diners along the harbourfront.

On the last day of you trip, pay a visit to one of the renowned universities that makes this place a hub of excellence in global education and innovation. Harvard and MIT offer guided campus tours, where you will learn about the history of these prestigious institutions, their notable landmarks and academic achievements. We also recommend paying a visit to the Harvard Museum of Natural History. After the morning tour, stop at Kendall Square (MIT) or Harvard Square for lunch. In both places, you will find shops, cafes and bookstores to explore.

In the afternoon, visit one of the city’s museums. The John F. Kennedy Museum & Library showcases the legacy of America’s 35th president. The Isabella Steward Garner Museum houses a collection of paintings, culture, tapestries and decorative art from European, Asian and American artists. The USS Constitution Museum provides great insights into what life was like at sea over two centuries ago through first-hand experiences like furling a sail, firing cannon, and even scrubbing the deck.

For your final dinner in Boston, enjoy fine dining at one of the many upscale downtown restaurants, like Menton, The Oceanaire Seafood Room, Ruth’s Chris Steak House, or Row 34 and Oleana near Cambridge.

Travelling to Boston for a few days? Travel insurance is invaluable even for short trips across the border, and may protects you against unexpected sickness and injury, covered cancellations, disruptions and even lost or damaged baggage. Find a travel insurance plan that suits you!

Travel insurance is underwritten by CUMIS General Insurance Company, a member of The Co-operators Group of Companies, administered by Allianz Global Assistance, which is a registered business name of AZGA Service Canada Inc.
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