5 Day Boston Itinerary

Welcome to Boston! Start your adventure at the heart of the city’s history: The Freedom Trail, a two-and-a-half mile long walking path that explores Boston’s historic sites. Begin your journey at Boston Common, America’s oldest public park. As you follow the trail, you will encounter significant landmarks such as the State House, the Granary Burying Ground where Paul Revere and John Hancock rest and the Old South Meeting House where the Boston Tea Party was planned.

Take a break for lunch when you reach Faneuil Hall, sampling local favorites such as clam chowder or lobster rolls at Quincy Market. After refueling, continue along the Freedom Trail to the North End where you can visit the Paul Revere House and the Old North Church. Continue onto Charlestown to visit the USS Constitution and Bunker Hill before circling back into the city.

In the late afternoon, make your way to the charming Beacon Hill neighborhood. Stroll down picturesque Charles Street, lined with antique shops and boutiques, and make sure to pass by Acorn Street, often called the most photographed street in America.

On the second day of your five-day Boston itinerary, dedicate your morning to exploring the vibrant Back Bay neighborhood. Begin with a leisurely walk down Newbury Street, known for its high-end shopping and beautiful brownstone buildings. Visit the Boston Public Library in Copley Square, a masterpiece of architecture featuring a stunning reading room and hidden courtyard. Take time to admire the Trinity Church and the towering John Hancock Tower in Copley Square before heading to the luxurious Raffles Boston for your reserved afternoon tea at Long Bar & Terrace.

In the evening, make your way to the legendary Fenway Park, home of the Boston Red Sox. Whether you catch a game, a concert, or take a tour of this historic ballpark, you will be immersing yourself in an essential piece of Boston culture.

Cross the Charles River to explore Cambridge, home to world-renowned universities. Start your day with a stroll through Harvard University’s campus or opt for an official tour to gain insight into America’s oldest university. Explore Harvard Square, sample a latte and pastry at Tatte and browse the extensive collection at the Harvard Book Store.

In the afternoon, head to MIT to admire its innovative architecture, especially the unique Stata Center designed by Frank Gerry. Stop by the MIT Museum to dive into the world of science and technology then spend the rest of your afternoon enjoying the Charles River Esplanade. Consider renting a bike or even a kayak for a different perspective of the city.

A five-day Boston itinerary would be incomplete without a visit to the beautiful Boston Harbor. Start at the New England Aquarium, where you can marvel at the giant ocean tank and enjoy the playful penguin exhibit. Afterward, head out onto the water by boat, either on a whale watch or on a Boston Harbor boat tour, to get a spectacular view of Boston’s skyline.

In the afternoon, explore the vibrant and newly developed Seaport District. Visit the boutique shops and the Institute of Contemporary Art (ICA) to see cutting-edge exhibitions. Local tip: The ICA is free every Thursday from 5-9 pm!

For a bit of interactive history, stop by the Boston Tea Party Ships & Museum. You will even get the chance to “throw tea” into Boston Harbor.

As the evening approaches, head into the North End, Boston’s Little Italy, for a culinary adventure. Consider taking a guided food tour to sample the neighborhood’s best Italian specialties. If you prefer to explore on your own, start with pizza at the legendary Regina Pizzeria, then wander down Hanover Street and Salem Street. Don’t leave without trying cannoli — both Mike’s Pastry and Modern Pastry offer delicious options, creating a major local debate on which is the better choice. I suggest trying both, for research purposes, of course.

On your final day, immerse yourself in culture at the Museum of Fine Arts (MFA), where you can explore everything from ancient Egyptian artifacts to contemporary American art, or the Isabella Stewart’s Gardner Museum, a Venetian palace in the middle of Boston that houses an extensive international art collection.

In the afternoon, discover the charm of the South End neighborhood. Known for its Victorian row houses and quaint parks, the South End offers a more laid-back Boston experience. Walk down Tremont Street to explore local boutiques and art galleries. Be sure to visit the SoWa Art and Design district, a hub of creativity where you might catch artists at work in their studios. If you are visiting Boston on a Sunday between May and October, don’t miss the SoWa Open Market for local art, food and vintage finds.

End your trip with a sunset view from the Prudential Center Skywalk Observatory.