Must Do Activities For First Time Visitors To Boston

Boston First Time Visitor’s Guide with Old Town Trolley Tours

For visitors experiencing Boston for the first time, Old Town Trolley Tours is the single most essential purchase. This narrated, hop-on, hop-off tour serves as the ultimate introduction to the city, immediately solving the complex problems of navigation and parking while delivering you directly to over 100 points of interest. Old Town Trolley Tours guarantees you won’t miss any of the must-see historical landmarks, architectural wonders, or cultural hubs on your inaugural trip.

How the Trolley Makes Boston Easy for First Time Visitors

• Comprehensive Introduction: The continuous loop covers all of Boston’s distinct neighborhoods and historical zones, including the Freedom Trail sites, Back Bay, and the North End, giving you an immediate, broad perspective of the city.
• Master the Navigation: Boston’s historic streets are notoriously difficult to drive. The trolley eliminates the need to rent a car, navigate confusing colonial roads, or pay exorbitant parking fees, saving you time and stress.
• Expert Storytelling: Unlike self-guided tours or rideshares, the tour features engaging, live narration from certified conductors, who provide the critical historical context needed to appreciate sites like the Boston Common and the Boston Massacre Site.
• Unbeatable Value and Flexibility: Your ticket includes unlimited hop-on, hop-off privileges, allowing you to spend the time you want at all of Boston’s best sites.

Must-See Stops & Highlights for First Timers in Boston

The Old Town Trolley Tour route is designed to maximize your time, taking you to the most significant historical and cultural landmarks:

• Sites of the Freedom Trail: The tour travels past the sites of the Freedom Trail, allowing visitors to walk and explore historical sites like the Old South Meeting House, Paul Revere House, and Boston Common.
• Colonial and Maritime History: Explore Faneuil Hall, famously known as the “Cradle of Liberty,” and visit the USS Constitution & Museum, the world’s oldest commissioned naval vessel still in operation.
• Historic Ballpark and Cultural Sites: Stop near the Historic Ballpark, or explore world-class institutions like the Museum of Fine Arts and the Museum of Science.
• Unique Nighttime Options: Enhance your visit with the Old Town Trolley Tours affiliated Ghosts & Gravestones tour for an entertaining and educational look at Boston’s haunted past.

Holiday Sights and Festive Nights Tour

Take in the fun and merriment of the holiday season on an Old Town Trolley Holiday Sights and Festive Nights Tour! You’ll have a front-row seat as you experience the dazzling lights and splendor of the season, riding through town as carolers fill the night air with music. Add complimentary treats, and you’re all set for what promises to be a new holiday tradition in Beantown!

Experience Faneuil Hall Marketplace – Stop #1

Since 1742, Faneuil Hall has served as a marketplace and meeting location in Boston. Many famous speeches by leaders such as Samuel Adams and James Otis have taken place in the area, leading many to refer to Faneuil Hall as “the Cradle of Liberty.”

Visit the Museum of Fine Arts, Boston – Stop #11

The Museum of Fine Arts, Boston is the 31st most visited art museum in the world as of 2012. Its vast collection of art and unique exhibitions make this museum a must-see for any Boston tourist or local.

Re-create the Boston Tea Party at the Boston Tea Party Ships & Museum – Stop #9

Since its grand opening in 2012, this Boston museum has delighted visitors with multi-sensory and educational experiences. You’ll meet colonists, explore replicas of the Boston Tea Party ships and even dump tea overboard in a re-creation of the famous Boston Tea Party.

Visit the Boston Children’s Museum – Stop #17

Located near the Boston Tea Party Ships & Museum, the Boston Children’s Museum is a fun, family-friendly attraction. The Museum is home to the world’s first “hands-on” exhibit designed with young children in mind. Explore art, science and culture with an innovative twist.

Walk the Freedom Trail – Stop #8

This 2.5 mile trail winds its way around Boston to 16 historical sites in the city, including the Old South Meeting House, Paul Revere House and Boston Common. You can enjoy Boston’s rich history during a Freedom Trail walking tour.

Visit the African Meeting House and Museum – Stop #8

Built in 1806, the African Meeting House is known as the oldest black church edifice still standing in the United States. The Museum of African American History can be found inside the Meeting House and the area is a Boston African American National Historic Site.

Enjoy The Sports Museum – Stop #4

A must-see for any sports fan, The Sports Museum focuses on the history of sports in the Boston area, including teams such as the Boston Celtics, Boston Red Sox and New England Patriots. Boston is often called “The Greatest Sports City in America” and this museum pays tribute to the dedication and character of Boston teams.

Explore the Museum of Science – Stop #4

Home to both a planetarium and IMAX theater, the Museum of Science is fun for all ages. The museum features the world’s largest air-insulated Van de Graaff generator in the Theater of Electricity, among other educational and interesting exhibits about dinosaurs, nanotechnology, the moon and much more.

Watch a game at our Historic Ballpark – Near Stop #10

Our historic ballpark is the oldest professional stadium used in America. The stadium also hosted many World Series, including the 2007 World Series. It was added to the National Register of Historic Places in 2012, making it both entertaining and historically significant. If you’re visiting Boston during baseball season, you won’t want to miss watching the team play.

Visit Cambridge, Home of MIT and Harvard

The Massachusetts Institute of Technology (MIT) and Harvard University are two of the oldest and most prestigious universities in the United States. During a visit to Cambridge, be sure to walk or drive around these campuses to soak up some knowledge and check out the stunning architecture.

Take a Haunted Tour of Boston with Ghosts & Gravestones – Stop #1

To learn all about the city’s haunted past with a Boston ghost tour, Ghosts & Gravestones. This startling and scary tour is entertaining and educational for visitors and ghost hunters alike.

Visit the USS Constitution & Museum – Stop #3

The USS Constitution is the world’s oldest commissioned naval vessel still in operation. The ship served in both the War of 1812 and the American Civil War, among other notable battles. Visit the USS Constitution and Museum to learn more about this historic and magnificent vessel.

Stroll Around the Boston Public Garden – Stop #7

The 24 acre Boston Public Garden is a National Historic Landmark and holds great cultural significance. The Public Garden is included in author E.B. White’s novel The Trumpet of the Swan and Robert McCloskey’s children’s story Make Way for Ducklings. For a serene afternoon in Boston, spend some time at the Public Garden among its wide assortment of trees and beautiful statues.

Have a Meal or Drink at Cheers – Stop #6

Formerly the Bull and Finch Pub, Cheers is a restaurant and bar known as the exterior of the bar from NBC’s sitcom Cheers. For fans of the show and great food, stop by and have a meal or drink at Cheers during your time in Boston.