Top Massachusetts Cultural Tours

Tour Provincetown aboard our authentic Trolleys featuring the history of the Mayflower's first landing, the development of our famous art colony, the beauty of the National Seashore and much more. Tours available from May thru October.

We are unique as we are the oldest tour company on the historic island of Nantucket. From the early days when Chester Barrett founded the company and drove a horse and buggy, to today, we are ready to give you a great truthful and historical view of Nantucket. We are you premier choice for bus tours, van tours, and wedding transportation in Nantucket, MA You will see a narrated tour where we show you old lighthouses, the village of Siasconset on the East end of the island, rose cover cottages, as well as the old railroad and either the oldest or 2nd oldest house on island. You will really enjoy seeing the island from this perspective. The 1.5 hour time is just enough time to see the sights and plan where to spend the rest of your visit on island. We can also do private and large group tours, inquire by calling.

For anyone thinking of attending Harvard, or for those who simply want a glimpse of college life at the famous university, this tour is a must. Get an exclusive account from current Harvard students, who provide key insights into the life and times at Cambridge with a theatrical, humorous flair. Check out the old buildings at Harvard Yard and Harvard Square and learn about the school’s storied past. Illustrated map of Harvard Square included. Choose from several departure times throughout the day.

Discover a whole new side of baseball history with the help of a guide on this tour of Fenway Park, one of baseball’s most beloved stadiums. Revisit the careers of Red Sox greats like Ted Williams, Babe Ruth, and Carl Yastrzemski, celebrate the club’s numerous World Series titles, and tour famous stadium locales like the ‘Green Monster,’ ‘Pesky’s Pole,’ and the Fenway Park Living Museum. It’s ideal for baseball fans, be they locals or tourists.

Explore downtown Salem through the lens of witchcraft and the witch trials on this walking tour. Led by your guide, learn about the history of occultism, spiritualism, and the contributing factors that led to the creation of modern-day Salem. There are no ghosts or scary stories here, making this experience suitable for families.

Explore Boston’s top 3 attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary and fun photo tips to help you capture memorable photos of your adventure. Discover the history behind Back Bay's the iconic architectural landmarks in Copley Square. We’ll take a scenic stroll in the Boston Public Garden to see the colorful flowerbeds and the famous Swan Boats. And for the grand finale in Beacon Hill, find out why Acorn St. is the most photographed street in Boston. Designed for history buffs, urban explorers, smartphone users, and casual photographers, this guided walking tour blends engaging historical commentary with photo tips. It is not a technical photography class.

Explore Boston’s Freedom Trail independently and on your own time with this audio walking tour. The tour never expires, so take your time to learn about Boston’s history and explore its center in the company of the audio guide. An easy-to-navigate app with GPS allows you to wander confidently throughout Boston.

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive. Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort. This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories. — Discover the distinctive Victorian architecture and intricate cottages — Explore the historical significance of Oak Bluffs as a cultural hub — Enjoy scenic ocean views and shaded park paths during your stroll — Perfect for history buffs and those seeking a unique coastal experience

Learn about the Battle of Lexington and Concord at your own pace with this self-guided audio driving tour. Download the app and choose to start the tour whenever you are ready. Drive the route of the first battle and listen to the stories that queue up to play with your GPS.

Experience the Black Heritage Trail and get to know more about Civil War-era Boston on this small-group walking tour. In the company of a guide, head out into Beacon Hill and hear stories about the Underground Railroad, Boston Brahmins, and other historical facts. Enjoy a focus particularly on the Civil War years.

Explore Boston’s Freedom Trail as you wish with this self-guided audio tour. Download the iPhone or Android GPS app and start along the trail when it suits you. As you wander between the sites, dip in and out of their backstories, deep-dive into topics that grab your interest, and stop and resume the audio when you wish. The benefit? You’ll enjoy more flexibility than on a fixed-itinerary tour and have more information at your fingertips than if exploring alone.

Eat your way through Boston’s North End and learn about its history with this small-group tour. Explore the neighborhood’s Italian heritage in the company of a guide and stroll through the area’s scenic streets. Enjoy a local lunch at a North End eatery and hear stories about the neighborhood’s past.

Discover the thrilling history of Boston on this immersive walking tour of the Freedom Trail. Hear tales of Redcoats, smugglers, riots, and midnight riders while reliving the American Revolution as you explore all 16 official sites of the trail. Learn about Boston’s leadership in abolition, women’s rights, education, and immigration over its 400-year history. Explore downtown Boston, hearing stories of legendary figures such as Paul Revere, John Hancock, and lesser-known pioneers and patriots.

Take a deep dive into the history of the American Revolution on this walking tour of Boston. Your historian guide will focus on the years between 1760 and 1775, a tumultuous time with plenty to talk about. Stroll the Freedom Trail and ask your guide questions along the way to learn things most tourists miss.

Learn more about the history of Lexington and Concord from the comfort of an air-conditioned trolley. Sit back, relax, and listen to the live commentary from your guide dressed in period costume as you pass Lexington and Concord’s heritage sites. This isn’t a hop-on, hop-off bus so you can remain on the trolley for the full 90 minutes. Gratuities are not included.

Set sail at along the Massachusetts' North Shore, during your visit to Salem. Board the historic schooner yacht What and If and drift along the coastline, taking in the sights of Salem. Relax on the deck or take a turn at the wheel of this beautifully restored classic sailing yacht, which was built in 1939 by General George Patton. Soft drinks and bottled water are provided, and a cash bar is available on board.

Go behind the scenes of Boston’s iconic seafood scene with a local guide on a tour that helps you explore the city like a local. Explore the oldest working fish pier in the US, visit family-run seafood shacks, and enjoy tastings of lobster rolls and clam chowder. Plus, learn about sustainable practices and Boston Harbor’s remarkable transformation.

See Boston from a whole new angle aboard a Boston Harbor evening cruise. Watch the sunset from the water, and glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, the USS Cassin Young, and more. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night, and sip a cocktail (own expense) from the onboard bar as you relax and enjoy the views.

Explore Martha’s Vineyard efficiently on a private tour designed for travelers with limited time. This narrated drive offers a personalized overview of the island’s towns and scenic coast without navigating on your own. Learn local history and context from a dedicated guide while traveling comfortably between key areas, making the most of a short visit ashore.

Unlike other Salem walking tours, this witch walking tour is led by a practicing witch, so you can learn about the history of witchcraft, as well as how it’s practiced today. Walk through the streets of Salem and learn about the dos and don'ts of modern-day witchcraft, stopping at Salem's Old Burying Point Cemetery along the way.

Walk Salem's most haunted streets and uncover the devastating true story of the 1692 witch trials — told the way only a lifelong local of old Salem can tell it. This tour is a favorite with families and curious kids of all ages. Named one of TripAdvisor's Top 10 Salem Walking Tours 2026, step into 400 years of mesmerizing history. Pass centuries-old buildings — could they still be haunted? Enjoy some Hocus Pocus stops. Then be shocked by Salem's lesser known history, and the question nobody thinks to ask: Why are there no Sheriffs located in Salem anymore? Every tour ends with time for questions and recommendations for where to eat, shop and explore by request. Hate the crowds? Pick our early morning 8:30am slot. We look forward to meeting you. The tour's starting point is: The East India Fountain at 158 Essex St Salem, MA 01970. Length is 60-90 minutes depending on pacing times and needs. This is an outdoor only walking tour, we do not go inside any buildings. See you in Salem!

If you want to explore Salem's haunted history without getting lost in the crowd, go at your own pace with an affordable, self-guided smartphone tour. Simply download the touring app to your phone, and start and stop the tour on your own schedule as the pre-recorded narrator shares the history of haunted locales like the Ropes Mansion, Salem Witch House, and Old Burying Point Cemetery, where many witch trial victims were laid to rest.

Don’t waste time looking for the ideal place to eat as you walk the cobblestone streets of Boston’s North End. Join other passionate foodies to snack your way through the neighborhood’s hidden gems. Your guide directs you to a hidden Italian bakery, an authentic Italian salumeria, and a family-run pastry shop. Visit the Old North Church (or equivalent alternative) and enjoy a rich cappuccino or bold espresso with a pastry.