The Ultimate 3-Day Boston Itinerary for First-Time Travelers

Welcome to Boston! Known for its role in the American Revolution, its educational excellence (home to Harvard University and MIT), the Boston Cream Pie, and much more… this city has many claims to fame. There are lots of fascinating landmarks to check out, neighborhoods to explore, and food to try, making it hard to plan a quick trip that covers all bases. If you’re in the process of planning a trip, look no further—Civitatis has you covered with the ultimate 3-day Boston Itinerary. Let’s get into it!

Day 1

Morning – Freedom Trail

The best way to begin your journey through Boston is at the Freedom Trail, a 2.5-mile (4-kilometer) redbrick path that leads you past Boston’s most historic landmarks. Start at Boston Common, a gorgeous public park in the middle of the city, and continue along the route, which is clearly signposted. Along the way, you’ll discover 400 years of history encompassed by 16 sites related to the American Revolution—the site of the Boston Massacre, Faneuil Hall, Paul Revere House, USS Constitution, and Massachusetts State House are just some of the stops along the trail. On this Best of Boston free walking tour, you’ll get to see the main landmarks and gain a deeper insight into the city’s history, accompanied by an expert tour guide. Alternatively, you can visit some of the city’s historic taverns along the Freedom Trail on this Boston Independence pub crawl, during which you’ll learn about the role of beer and breweries in events like the landing on Plymouth Rock and the Boston Massacre.

Afternoon – Quincy Market & Public Market

The Freedom Trail and the Best of Boston tour, both finish at the Old Church in the North End, leaving you just a 12-minute walk, or a 5-minute drive from Quincy Market—the next stop on our Boston adventure! This market dates back to the early 19th century and is now one of the most popular tourist attractions in the city. Quincy Market was one of the first major city projects, built in a Greek Revival style, featuring wonderful Doric columns and a copper dome. This Boston guided tour includes a stop at Quincy Market if you want to visit it alongside a tour guide!

You can grab a bite here at Quincy Market. You’ll find clam chowder, lobster, poutine, mac and cheese… the works! However, the food in the market is generally quite expensive—you won’t find many Bostonians eating here. However, just around the corner, you’ll find Boston Public Market, which is better value, and has a much better-quality offering, which is much more popular among locals.

Evening – View Boston Prudential Center

After dinner, finish off your evening with a visit to the Prudential Center’s View Boston. This viewpoint offers stunning 360-degree panoramic views of Boston’s skyline, from the 52nd floor. Look over the Charles River, Harvard University, the Rose Kennedy Greenway, and more. If you don’t have dinner plans yet, maybe grab dinner in the Prudential Center, at the Beacon restaurant!

Day 2

Morning – Museum of Fine Arts

Start your second day in Boston with a visit to the Museum of Fine Arts. One of the finest museums in the country, home to a vast collection of art from all over the world, consisting of 500,000 works in total. Art lovers can enjoy classic works from celebrated European artists such as Monet, Renoir, Van Gogh, and Rembrandt, along with pieces from indigenous American cultures and Asia. History buffs can enjoy ancient artifacts from Egypt, Greece, and more! The Boston Museum of Fine Arts also features 10 seasonal exhibits at any given time, which are always worth checking out. Expect to spend 2-3 hours visiting the museum

Afternoon – Cambridge, Harvard, MIT

After exploring the Museum of Fine Arts in the morning, grab yourself some lunch and a coffee before continuing your day in Cambridge, an area widely renowned for its educational institutions, most notably Harvard and MIT. Both of these institutions have shaped some of the greatest minds in history, including Bill Gates and Barack Obama at Harvard, and Kofi Annan, and Buzz Aldrin at MIT.
Stroll through Harvard Yard, the historic heart of the university, where you can admire centuries-old architecture, visit the famous Widener Library, and rub the John Harvard statue’s foot for good luck. Explore Harvard Square, a lively area filled with bookstores, cafés, and street performers that capture the city’s vibrant academic atmosphere. The best way to see it for yourself is as part of this Harvard University walking tour. If you’re in the area and you have the Boston CityPASS®, definitely check out the Harvard Museum of Natural History, which is usually $10-$15, but is included with the pass.

If you’re interested in checking out Cambridge’s other major universities (and another one of the most prestigious in the world), take a look at this MIT walking tour. This technology university has long been at the forefront of technological research, and is, visually, strikingly different from Harvard, with its super modern architecture.

Evening – Charles River Esplanade

If you still have energy, and the weather is nice, take a relaxing post-dinner walk along the Charles River Esplanade. This walkway provides a lovely green space, with lots of grassy areas for picnicking, sports fields, boating docks, and more. The area is also often used for outdoor concerts, festivals, and fireworks displays. Most nights though, the esplanade provides a relaxing walkway, with tranquil views over the river, and magical sunsets—the perfect way to wind down after a busy day of adventure.

Day 3

Morning – Whale Watching

On our third and final day exploring Boston, kick off the day (ideally at 9 or 10 AM) at Waterfront, where from Long Wharf, you’ll board a catamaran and go whale watching! This whale-watching cruise will bring you to the Stellwagen Bank National Marine Sanctuary, home to humpback whales, fin whales, dolphins, and more! After a few hours of sailing, and lots of insights about these animals from your tour guide, you’ll make your way back to Waterfront. 

Afternoon: Italian Food in the North End

After the cruise, you’ll have worked up an appetite—the perfect time to make your way to the North End. This area has a history dating back to the 1630s, making it the city’s oldest residential community. With its strong Italian American influence, this part of the city is known for its food. Along brick and cobblestone roads lined with old buildings, you’ll come across lots of incredible restaurants serving home-style Italian food, as well as some fantastic patisseries. If you’re big into donuts, you might consider this donut tour in the North End.

Evening: Boston Ghost Tour

What better way to cap off your Boston adventure than with a spine-tingling ghost tour? On this Boston ghost tour, step into the shadows of this storied city and uncover its eerie past as night falls. Learn about such mysterious figures as the elusive White Witch and the tragic tale of the Martyr Mary Dwyer. Also, discover one of the most haunted hotels in the United States, along with two spooky burial grounds that seem to echo with the voices of history.

More Activities to Fit into Your Itinerary

If you have a little bit more time and are looking to fill your itinerary with more activities, there are plenty more options with Civitatis! One of our favorite things to do in Boston during basketball season is to catch a Boston Celtics game at the TD Garden Arena. Even if you’re not a massive basketball fan, the atmosphere of the game alone makes the experience worthwhile. Also, check out the arena’s Sports Museum, which is included in your ticket, and gives you a deeper insight into the Celtics, as well as other teams like the Boston Red Sox and the New England Patriots.

Another great thing to do while in Boston is this day trip to the Plymouth Plantation. This plantation will bring you on a journey back in time to the mid-17th century in New England. Experience what life would have been like in small farming communities, as actors recreate living conditions and answer any questions you may have about what it was like at that time!

Visit Boston on a Budget

If you’re staying for a couple of days or more, and you plan on checking out the main landmarks and museums, definitely check out the check out the Go City: Boston All-Inclusive Pass, or the Go City: Explorer Pass. Depending on your itinerary, using these tourist cards can save you up to 45% on your trip.

When making your way around the city, use the MBTA or ‘the T’—the city’s public transport network, which includes subways, buses, and trains linking all of the city’s major tourist sites.

There you have it! That is our ultimate 3-day Boston itinerary. Of course, there’s plenty more to do in ‘the Hub’. If you’re still looking for ways you can fill your trip, check out more tours & experiences in Boston with Civitatis!