Top Things to do when Visiting Boston, Massachusetts

Boston features a vibrant culture with many activities for visitors to enjoy. Tourists can enjoy modern amenities like speed boat whale watching or pedal swan boat rides, or visitors can enjoy historic attractions, such as a walking tour of the waterfront. You can enjoy a delicious meal at a waterfront cafe, or visit a popular food truck. Whether you want to enjoy the great outdoors or visit a popular concert in the city, Boston has many things to do.

What to do in Boston

Enjoy a Tour with Tripshepherd Opening March 16th, 2022 we are happy to show you around the beautiful, historic city of Boston Both during the day and night with our brand new Scenic Boston Night Tour and Boston City Tour! All our tours provide guests with a fully narrated small-group tour (maximum 7 guests) in the comfort and style of one of our Mercedes Metris vans, they also all include all attraction admission fees ( no hidden fees) and skip-the-ticket line entry (avoid large crowds and long wait times). Best of Boston TourThis small-group 4-hour tour of Boston highlights the most prominent sites and attractions in the city. It includes visits to Harvard University's grounds, MIT Dome, the world's oldest naval vessel the USS Constitution, the historical Bunker Hill Monument, and a relaxing It includes visits to Harvard University's grounds, MIT Dome, the world's oldest naval vessel the sightseeing cruise to check out significant historical sites. You will also enjoy a narrated drive through the city passing by multiple points of interest! Scenic Boston Night TourEnjoy the glow of Boston at night with this 3-hour small group tour, offering unique experiences, both on land and on the water of the harbor such as a stunning sunset cruise, city drive, and a charming north-end walking tour featuring top attractions and visitor experiences. The tour includes visiting the iconic Skinny House, Paul Revere Statue & house, George fountain & the North End Old Church. Boston City Tour Experience the Best of the city of Boston on this 2-hour small-group tour enjoy a narrated drive passing many points of interest and get the opportunity to experience top attractions like the iconic Harvard University grounds, MIT Dome, the historic Bunker Hill Monument, and the USS Constitution. Let us help you plan your next vacation to Boston, Massachusetts, and discover everything the Cradle of Modern America has to offer.

Take a Step Back into American History

Boston is steeped in rich American history. Here are some historical stops that would be a must-see for any history junkie or anyone interested in learning about the city’s roots when visiting Boston.

The Freedom Trail

No trip to Boston would be complete without a stop along the Freedom Trail which connects many significant sites of America’s history along 2.5 miles. The trail features sixteen historic sites starting with the Boston Common to Paul Revere’s house in the North End, including museums, churches, meeting houses, parks, the USS Constitution, burying grounds, and historic markers along the way. Each site along the trail tells its very own story surrounding the American Revolution and beyond.

Faneuil Hall Marketplace

Faneuil Hall Marketplace also known as “the home of free speech” and the “Cradle of Liberty” was constructed in 1764, built by artist John Smilbert who used English Country Markets as an inspiration. Sitting atop Faneuil Hall is an 80-pound golden grasshopper, the most famous weather vane in the city, designed by Shem Drowne. During the war of 1812, it is said that in an attempt to spot spies, anyone who responded incorrectly to the question: What is on the top of Faneuil Hall? Would be considered suspicious. The Hall since has been the setting for 300-500 new citizens swearing-in, taking the Oath of Allegiance inside the Great Hall.

USS Constitution

Included in our new Boston City Tour, is the world’s oldest commissioned warship afloat - the USS Constitution, also known as “Old Ironsides” located in the former Charlestown Navy Shipyard. Launched in 1797, this wooden-hulled three-masted heavy frigate was one of the original frigates authorized by the Naval Act of 1794. The ship was used during the War of 1812 against the United Kingdom defending numerous warships including HMS Guerriere. The ship retired from service in 1881, serving as a receiving ship until 1907, and in 1934 she completed a 3-year, 90-port tour of the nation, celebrating her 200th birthday in 1997. Today, you can visit the USS Constitution Museum to understand the navy’s role in war and peace through exhibits, daily programs, and historic demonstrations put on by her crew of 60 officers and sailors.

Bunker Hill Monument

The Bunker Hill Monument, located along the Freedom Trail in Charlestown is important to the American Revolution, this granite monument was built to commemorate the Battle of Bunker Hill (1775) the very first major battle of the Revolutionary War. Today, it is home to the Bunker Hill Museum where visitors can view dioramas, murals, and artifacts from the battle including a cannonball, a sword, and a snare drum, among many other items. Visit the monument on our Best of Boston Tour, featuring stops at the USS Constitution, Bunker Hill Monument, a narrated drive, and a Boston harbor cruise! Tripshepherd Fun Fact: the Bunker Hill Monument, standing at 67 m, was the tallest memorial prior to the Washington Monument!

Catch a Baseball Game at Fenway Park

Take a tour of America’s most beloved ballpark, Fenway Park, and attend a Red Sox Game! Since 1912, fans have flocked to Fenway to watch the home team play in the heart of Boston, the oldest active ballpark in the MLB. Offering a variety of tours for individuals, groups, any occasion, and premium experiences, fans are able to get an exclusive look at the historical Fenway Park and get a chance to see the home team win! Tripshepherd Fun Fact: in 1914 elephants took over the stadium when the city zoo purchased three circus elephants Mollie, Waddy, and Tony for their coming-out party attended by 60,000 kids and their parents.

Admire Art or Culture at one of Boston’s Museums

When looking to stay warm and indoors visit some of the many museums Boston has to offer including; the John F. Kennedy Presidential Library and Museum, a great stop for anyone interested in the 35th President of the United States. Explore the many exhibits highlighting Kennedy’s life from his younger years onwards to his presidential run and inauguration, including an exhibit on his wife, the former first lady, Jacqueline Kennedy. When traveling with kids the Boston Children’s Museum is a great stop. Recognized as a pacesetter for children’s exhibitions, educational programs, and curriculums, the museum offers children the opportunity to explore exhibits surrounding literacy, performing arts, science, math, cultures, and health and wellness among others. Explore Boston’s Museum of Fine Arts. Founded in 1870, the museum is known as one of the most comprehensive art museums in the world with the collection encompassing nearly 500,00 works of art! This fine art museum welcomes more than one million visitors every year to experience art from around the world featuring special exhibitions and innovative educational programs.

Walk Around and Explore Boston

Boston’s manageable size has made it one of the most walkable cities in America largely due to the 1990’s Big Dig Project which sunk the city’s major highways underground, replacing them with pedestrian greenways and making it even more friendly for those on foot.

Harvard Yard

No trip to Harvard is complete without making a stop at the famous Harvard Yard, the oldest part of the Harvard university campus. This historic site and modern crossroads contain most of the freshman dormitories, the universities most important libraries, and Memorial Church along with several classroom and department buildings. Tripshepherd Fun Fact: The Statue of Three Lies, located in Harvard Yard is the third most popular and photographed statue in the United States! The statue features three incorrect facts including stating that it depicts John Harvard the founder of the university when instead it is actually a random student model used by the sculptor - can you point out all three incorrect facts? Another great place to stroll around is Harvard Square, a place of history, books, ideas, and learning offering bookstores, coffee houses, and eclectic fine shopping. Here you can watch some folk music or visit an old theater.

Boston Public Garden

Explore the first public botanical garden in America, located on Charles Street, the other side of Newbury street. Created in 1634, the garden is decorative and flowery featuring meandering pathways excellent for strolling especially on those sunny, warm, summer days. The park was designed with a Victorian touch with designs of vibrant floral patterns and utilizes new techniques of collecting, hybridizing and propagating plants. The garden offers visitors the opportunity to admire the colorful and unusual plants at the Lagoon, admire the monuments and fountains located on the grounds, and even enjoy the Swan boats. Whether you decide to spend your time marveling at American history, strolling through beautiful gardens and neighborhoods, watching baseball, on a fully guided tour, exploring Boston’s museums, or doing all of the above there is something for everyone!