Boston is a city rich in tradition, renowned for its Revolutionary War landmarks, prestigious universities, and historic neighborhoods. Its blend of colonial charm and modern appeal draws travelers from around the world. Whether you’re here to explore its historic sites, enjoy its renowned seafood, or take in the city’s cultural offerings, here’s what you need to know to make the most of your visit to Boston.

Boston Harbor and Waterfront

Boston Harbor and Waterfront

What’s the Best Time to Visit Boston?

The best time to visit Boston is in the late spring (May and June) or early fall (September and October). These months offer pleasant weather for exploring the city’s historic sites and neighborhoods. The fall foliage in October is particularly stunning, while late spring provides a chance to enjoy outdoor activities without the summer crowds.

What’s the Cheapest Month to Fly to Boston?

January tends to be the cheapest month to fly to Boston, as it falls in the post-holiday period when fewer travelers are visiting. February and early March can also be affordable times to book flights, though the weather during these months can be quite cold.

Public Garden, Boston

Public Garden, Boston

How Far in Advance Should I Book a Flight to Boston?

To get the best deals, book your flight to Boston at least two to three months in advance. Prices can fluctuate, so keeping an eye on flight comparison tools and setting up fare alerts can help you secure a good price.

How Many Days in Boston Is Enough?

A three- to four-day stay is typically enough time to explore Boston’s key attractions, such as the Freedom Trail, the Boston Common, and the Museum of Fine Arts. If you plan to take day trips to nearby areas like Cambridge or Salem, adding an extra day or two would give you more flexibility.

Faneuil Hall and Quincy Market, Boston

Faneuil Hall and Quincy Market, Boston

How Can I Save Money on a Trip to Boston?

To save money on a trip to Boston, consider visiting during the off-season (winter months), using public transportation instead of renting a car, and staying in neighborhoods outside the downtown area, such as Cambridge or Somerville. Also, take advantage of free or low-cost attractions, like walking the Freedom Trail, exploring the Boston Public Garden, or visiting museums on free or discounted admission days.

What Are the Cheapest Places to Fly into in Boston?

Boston Logan International Airport (BOS) is the primary airport serving the city. While it is the main gateway, some travelers find cheaper flights by flying into nearby airports like Manchester-Boston Regional Airport (MHT) in New Hampshire or T.F. Green Airport (PVD) in Rhode Island, then taking a bus or rental car to Boston. However, for convenience, Boston Logan is typically the best choice.

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Fenway Park, Boston

Fenway Park, Boston

FAQs: 

Q: What are the must-see attractions and activities in Boston?
A: Boston is home to a wealth of historic sites and cultural activities. The Freedom Trail is a must-do, guiding visitors through 16 significant Revolutionary War landmarks. The Boston Common, the oldest public park in the U.S., is another must-see, along with the nearby Public Garden. Art lovers should visit the Museum of Fine Arts or the Isabella Stewart Gardner Museum. For a more interactive experience, the Boston Tea Party Ships and Museum offers a hands-on look at history. Fenway Park is a top destination for baseball fans, while Harvard Square in nearby Cambridge offers a taste of the college-town vibe.

Q: What are the best neighborhoods to stay in in Boston?
A: Boston’s best neighborhoods for visitors include Back Bay, which is known for its beautiful brownstones and proximity to shopping and dining on Newbury Street. The North End is ideal for those interested in history and Italian cuisine, as it’s home to the Old North Church and fantastic restaurants. Beacon Hill is charming with its narrow, cobblestone streets and historic homes. For a more modern atmosphere, the Seaport District offers newer hotels, waterfront views, and excellent dining options.

Q: What are the local transportation options in Boston?
A: Boston is a walkable city, and many visitors prefer to explore on foot, especially in areas like Downtown, Beacon Hill, and the Back Bay. The “T,” Boston’s subway system, is a convenient option for getting around the city and to nearby areas like Cambridge. Buses and commuter trains are also available. For short distances, rideshares and taxis are common, and bike-sharing services like Bluebikes are a popular way to explore during warmer months.

Q: What are the best day trips from Boston?
A: Boston offers plenty of day trip options. Head to Cape Cod for a scenic coastal escape, or visit Salem for its history and witch-related attractions. Lexington and Concord are ideal for history buffs, with sites tied to the Revolutionary War. Newport, Rhode Island, offers a chance to explore Gilded Age mansions, while Portsmouth, New Hampshire, provides charming coastal views and a rich maritime history. For outdoor enthusiasts, a trip to the nearby Blue Hills Reservation offers hiking with views of the city.

Q: What are the best seasonal events or festivals in Boston?
A: Boston hosts a variety of seasonal events and festivals. In the spring, the Boston Marathon is a major event, drawing runners and spectators from around the world. The Boston Harborfest in the summer celebrates Independence Day with fireworks, reenactments, and historical tours. In the fall, the Head of the Charles Regatta draws rowing teams from around the globe. Winter events include the tree lighting ceremonies around the city and the Boston Wine Festival.

Q: What are the best historical landmarks to visit in Boston?
A: Boston is steeped in history, and some of the best historical landmarks include the Paul Revere House, the Old State House, and Faneuil Hall, all of which are part of the Freedom Trail. The Boston Tea Party Ships and Museum offers a reenactment of the famous event. The USS Constitution, also known as “Old Ironsides,” is the world’s oldest commissioned warship still afloat and is a must-visit for naval history enthusiasts. The Massachusetts State House, with its iconic golden dome, is another historic site worth visiting.

Q: Where can I find the best seafood in Boston?
A: Boston is famous for its seafood, and you can find some of the best at local institutions like Legal Sea Foods, which has several locations across the city. The Union Oyster House, America’s oldest continuously operating restaurant, offers classic New England dishes like clam chowder and oysters. Neptune Oyster in the North End is a smaller spot known for its lobster rolls. For waterfront dining, visit Atlantic Fish Co. or The Barking Crab for fresh catches and harbor views.

Did we leave out your favorite thing to do in Boston? Tell us about it in the comments below! 

About The Author

Chris Caggiano is a writer and editor with decades of experience in a wide variety of topics. His real love is the theater, but he also enjoys visiting art museums, riding roller coasters, snow skiing, and collecting Swedish glass and eccentric teapots. Chris is also a theater critic and a long-standing member of the Outer Critics Circle. Chris graduated from Boston College, much longer ago than he cares to admit. And more than anything, he loves his Cocker Spaniel, Oscar.