Build your own Boston itinerary

Explore Boston’s best sights with customizable options for every schedule.

Edited by Kaitlyn Dreyling | December 18, 2025

Explore Boston on your schedule

Boston’s top attractions are closer than you might expect. In this city, centuries-old landmarks, vibrant neighborhoods, and waterfront strolls are all minutes apart, making it easy to see more in less time. This guide invites you to explore Boston’s best neighborhoods, from the North End to Back Bay, whether you’re visiting for one day or three. Each itinerary flexes for weather, family-friendly activities, or business needs, with Massachusetts Bay Transportation Authority (MBTA) trains and buses as your backup to keep plans on track. Feel free to mix and match things to do based on your schedule and interests.

In this article: Customize your Boston itinerary

Day 1: Boston Common, Beacon Hill, and the North End

Day 2: Seaport and the Boston Harborwalk

Day 3: Fenway-Kenmore and Back Bay

Bonus: Half-day in Cambridge

Boston Logan International Airport logistics

Day 1: Boston Common, Beacon Hill, and the North End

Begin your Boston adventure in the city’s historic core. Grab coffee and stroll the tree-lined paths of Boston Common, America’s oldest public park, before moving on to the adjacent Public Garden for a seasonal Swan Boat ride. From the parks, wander the picturesque streets of Beacon Hill, past the charming brick rowhouses and the iconic Acorn Street photo stop. In the afternoon, follow the Freedom Trail’s 2.5-mile (4-kilometer) red brick path north from Boston Common to the Bunker Hill Monument in Charlestown. Depending on your timing, you can explore 16 nationally significant historic sites along the way, including Faneuil Hall and Old North Church. Make sure to pause for homemade pasta, fresh cannoli, and a cappuccino in the North End. Stay steps from the Freedom Trail and TD Garden arena at Canopy by Hilton Boston Downtown, where vibrant design, thoughtfully curated amenities, and complimentary Canopy Bikes set you up for local exploration.

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Day 2: Seaport District and the Boston Harborwalk

Expand your Boston itinerary with a day in the Seaport. Start your morning with breakfast at a bakery, followed by an exploration of the area's rotating collection of public art installations. Next, enjoy a scenic stroll on the Harborwalk, a public walkway that spans nearly 50 miles (80.5 kilometers) of waterfront paths. The Seaport segment offers iconic, unobstructed views of the downtown skyline, perfect for photos. Spend your afternoon browsing the galleries and exhibitions at the Institute of Contemporary Art (ICA), or, if you’re traveling with kids, explore the Boston Children's Museum. Alternatively, enjoy the green spaces, like the rooftop garden at the District Hall, or relax at Fan Pier Park. During the summer months, consider enhancing your experience with a harbor cruise for sweeping city views. As evening falls, watch the sun set at Fan Pier Park before hopping on the MBTA Silver Line to reach downtown in minutes, where you’ll find a broader array of dinner and nightlife options. For immediate Harborwalk access, Hampton Inn Boston Seaport District welcomes you with free hot breakfast, modern guest rooms, and a short walk to the water’s edge.

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Day 3: Fenway-Kenmore and Back Bay

Begin with a tour of Fenway Park, home of the Boston Red Sox, then grab lunch at one of the lively bars on Lansdowne Street. In the afternoon, transition to Back Bay to marvel its famous architecture, including Trinity Church in Copley Square and the historic Boston Public Library. On rainy or winter days, explore the Museum of Fine Arts (MFA) for world-class collections or the Isabella Stewart Gardner Museum for art in a Venetian-style setting. As the sun sets, Newbury Street’s shops and restaurants invite lingering, while the Esplanade’s riverside paths are perfect for a dusk walk. The Green Line connects your stops via the Kenmore, Hynes Convention Center, and Copley stations. Hilton Boston Back Bay places you near Fenway, the MFA, and Newbury Street, with spacious guest rooms and a welcoming lobby bar for unwinding after a day of discovery.

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Bonus: Half-day in Cambridge

If time allows, add a half-day adventure to the city of Cambridge for a fresh perspective. Start your morning exploring Harvard Square, the historic epicenter of Harvard University. Spend time browsing the iconic bookstores, indie cafés, and shops, and consider dipping into one of Harvard's renowned museums, such as the Harvard Art Museums or the Museum of Natural History. From Harvard, you can tailor your afternoon: either walk toward MIT to explore its unique architecture or head to the Charles River for scenic paths and green spaces before returning to Boston. The MBTA Red Line connects Harvard and MIT, with rideshare options for fast hops. If you choose to stay overnight, DoubleTree Suites by Hilton Hotel Boston – Cambridge offers a restorative stay along the Charles River with a free shuttle to Harvard Square, New England Aquarium, and Back Bay Boston.

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Boston Logan International Airport logistics

If your Boston visit starts late or ends with an early flight, a stay near the airport streamlines your plans. Hilton Boston Logan Airport offers direct terminal access via a covered walkway, a free 24-hour on-demand shuttle service to transit and water taxi, and several on-site dining options for busy travelers. You can reach downtown quickly for last-hour sightseeing or enjoy a restful night before your journey home. This option is ideal for business travelers, families with tight schedules, or anyone seeking a smooth arrival or departure.

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Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.

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