Exploring Boston: A Three Day Itinerary

Boston, the city where history whispers through cobblestone streets and modernity hums in trendy neighborhoods. As you step foot in this dynamic metropolis, you'll be greeted by a perfect blend of old-world charm and contemporary energy. From the Freedom Trail to the picturesque Charles River, Boston beckons with open arms, inviting you to explore its nooks and crannies.

I was fortunate to have been in autumn. Coming in to land at Logan International Airport I was astounded by the warm hues of autumn leaves, truly a magical sight, an awesome time to visit. Here’s a suggestion on a three day itinerary.

Boston Faneuil Hall

Boston Day 1: Explore the History and Culture


  • Start your day at Faneuil Hall Marketplace, an iconic Boston landmark. Explore the shops and grab a quick breakfast or coffee.
  • Join a Freedom Trail Guided Tour from Faneuil Hall. This 2.5-mile-long trail will take you through 16 historical sites, including the Massachusetts State House, Paul Revere’s House, and the Old North Church.


  • Enjoy a classic New England meal at Quincy Market within Faneuil Hall Marketplace. Try the clam chowder or a lobster roll.



  • Head to the vibrant North End neighborhood, known for its Italian heritage. Have a delicious Italian dinner at one of the many restaurants like Neptune Oyster or Mamma Maria.
  • Stroll along the charming streets and treat yourself to cannoli at the famous Mike’s Pastry.
Boston Museum Fine Arts

Boston Day 2: Art, Parks, and Harbor Views


  • Start your day at the Museum of Fine Arts. Explore a world-class collection of art, including works by Rembrandt, Monet, and American masterpieces.


  • Have lunch at Tatte Bakery & Café, a local favorite known for its fresh Mediterranean-inspired dishes.


  • Visit Isabella Stewart Gardner Museum, a stunning museum housed in a Venetian-style palace with a unique collection of art and beautiful gardens.
  • Spend the afternoon at Boston Common and the Public Garden, taking a leisurely swan boat ride and enjoying the serene surroundings or spice things up with the infamous Boston Duck Tour.


  • Head to Seaport District for dinner at a waterfront restaurant like Legal Harborside or The Barking Crab. Savor fresh seafood while enjoying harbor views.
Boston Harvard University

Boston Day 3: Academia, Harbor Islands, and Evening Entertainment


  • Explore the prestigious Harvard University campus in nearby Cambridge. You can take a guided tour or simply stroll through Harvard Yard.
  • Visit Harvard Square, known for its eclectic shops and cafes. Grab brunch at one of the local eateries.



  • Take a ferry to one of the Boston Harbor Islands (like Georges Island or Spectacle Island) for a nature escape and harbor views. Don’t forget to pack a picnic!
  • Return to the city and explore Newbury Street for shopping and people-watching.


  • If you were born in the 70’s or 80’s you will remember the sitcom “Cheers” with Ted Danson and Kirsty Alley. Head down to the Cheers pub for walk down memory lane. While you there enjoy a pint, something to eat and get a souvenir from the gift shop.
  • End your trip with a memorable evening at Boston’s Theater District. Catch a Broadway show or enjoy live music and comedy at one of the city’s famous venues like The Wilbur.

Top Activities in Boston


Is There Anything Fun in Boston?
Absolutely! Boston is a playground for fun-seekers. The city boasts a bustling nightlife, a thriving arts scene, and a range of entertainment options. Catch a game at the legendary Fenway Park, indulge in retail therapy on Newbury Street, or savor a delectable lobster roll at Quincy Market. Whether you’re a history buff, a foodie, or an art enthusiast, Boston has something to tickle everyone’s fancy.

Can You Do Boston in 2 Days?
While two days might not be enough to fully immerse yourself in all that Boston offers, you can certainly get a taste of its essence. Plan wisely by focusing on key attractions like the Freedom Trail, Boston Common, and the Museum of Fine Arts. Be prepared for a whirlwind adventure, but also consider an extra day or two the city at a more leisurely pace.

What Is Boston Popular For?
Boston is famous for its pivotal role in American history, being the site of events like the Boston Tea Party and Paul Revere’s ride. It’s also renowned for its prestigious universities like Harvard and MIT, as well as its passionate sports culture, with the Red Sox, Celtics, and Patriots winning the hearts of fans.

Is Boston Really Worth Visiting?
Absolutely, without a doubt! Boston’s unique blend of historical significance, diverse culture, and modern vibrancy makes it a destination that caters to various interests. Whether you’re a history lover, a food enthusiast, or simply looking for a lively urban experience, Boston won’t disappoint.

Is Boston or New York More Fun?
Ah, the age-old Boston vs. New York debate! Both cities have their own charm and attractions. While New York boasts its iconic skyline and Broadway, Boston offers a more compact and walkable layout, making it easier to navigate. Your preference will depend on whether you crave the hustle of the Big Apple or the intimate allure of Beantown. I’ve done both and can honestly say they are BOTH worth visiting and are completely different experience. See our article New York in 48 Hours.

Best Month to Go to Boston?
For the most pleasant weather and a myriad of outdoor activities, aim for late spring (May to June) or early fall (September to October). The city comes alive with blooming flowers or colorful foliage during these times, creating a picturesque backdrop for your adventures.

Is Boston Cheap to Visit?
Boston’s charm might be priceless, but it’s true that it can be on the pricier side for travelers. Accommodation, dining, and entertainment costs can add up. However, with careful planning, you can find affordable options, especially in terms of transportation and lodging if you’re open to exploring different neighborhoods.

Cheapest Month to Visit Boston?
If you’re looking to save some bucks, consider visiting during the winter months (January and February). While the weather might be colder, you can enjoy lower hotel rates and fewer crowds, giving you a chance to experience Boston at a quieter pace.

Is Boston a Walkable City? Absolutely! One of the highlights of Boston is its walkability. The city’s compact layout and well-designed streets make it a joy to explore on foot. Many of the major attractions, neighborhoods, and dining spots are within comfortable walking distance of each other.

Is Boston Walkable for Tourists?
Definitely! Tourists will find Boston to be a very walkable city. Whether you’re traversing the Freedom Trail, wandering through historic neighborhoods, or enjoying the beautiful waterfront, you’ll find that many of the must-see sights are conveniently close to each other.

Do You Need a Car When Visiting Boston?
Nope, leave the car behind! Boston’s efficient public transportation system, including the subway (locally known as the “T”) and buses, can easily get you around the city. Parking can be expensive and navigating the city’s streets can be a challenge, so relying on public transport is often the more convenient option.

Boston is like a well-seasoned dish that combines history, culture, and modern flair into a captivating experience. Whether you’re wandering the cobblestone streets, visiting world-class museums, or indulging in local delicacies, this city has an irresistible charm that keeps travelers coming back for more.
Planning a trip to Boston? Get your flights here and book excursion tickets to avoid the queues. 

Similar Posts