Top Massachusetts Cultural Tours

See all six beautiful towns of Martha’s Vineyard while learning more about their history, architecture and celebrity connections. This whistle-stop tour is an ideal introduction for first-time visitors–or equally a great way for those who usually stay in one place to see more. Key highlights include the whaling captain’s homes, Menemsha seaport, and Edgartown harbor, where the 1975 movie Jaws was filmed.

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.

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.

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 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.

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 Boston’s top 3 attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary of the famous sites along the way as well as fun photo tips to help you capture memorable photos of your tour experience. Discover the history behind Back Bay’s diverse architectural landmarks in Copley Square. Enjoy a scenic stroll through the Boston Public Garden to see colorful flowerbeds and the famous Swan Boats. For the grand finale, we'll visit Beacon Hill’s Acorn Street, known as known 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.

Walk Salem's most haunted streets and uncover the fascinating true story of the 1692 witch trials — told the way only a lifelong local of old Salem can tell it. Named one of the best Salem walking tours by TripAdvisor in the Top 10 Salem Walking Tours of 2026. Enjoy Hocus Pocus stops, thrilling ghost stories - then be surprised along the way by Salem's lesser known history, and the question nobody thinks to ask: Why are there no Sheriffs in Salem anymore? Enter Salem's stunning McIntire District with Revolutionary War, maritime, and pirate tales woven throughout. This is a historical tour enriched with some beloved ghost stories. Dining, shopping and exploring recommendations on request. Perfect for families, couples, day trips from Boston, solo travelers, haunted history tours, friends, bachelorette parties, bridal parties, and curious kids. This tour is guided in English only. Our meeting point: East India Fountain, 158 Essex St, Salem MA 01970. About 2 hrs. Outdoors only, no entry.

Explore Boston on a trolley tour that’s timed to catch sunset over the Charles River. Many Boston sites are illuminated—and uncrowded—at night, making this an ideal time to explore Boston Harbor, Cambridge, the Public Garden, and more. Live narration from an experienced guide showcases the stories and culture behind each place you visit, from stylish seaside neighborhoods to revolutionary war–era landmarks.

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.

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

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.

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.

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.

Calling all Sanderson Sisters superfans and curious coven members — it’s time to walk right into the magic! The Downtown Hocus Pocus Tour is a fun, leisurely paced walking adventure through the iconic filming locations of Disney’s “Hocus Pocus” in the heart of Salem. Along the way, your entertaining guide will share fun behind-the-scenes stories, strange coincidences, and local lore that may have inspired the film — plus a few surprises even hardcore fans might not know... This tour is created by the imaginations behind the award-winning and locally-staffed Salem Night Tour and it is perfect for families, film buffs, and anyone who wants a taste of the Hocus Pocus magic without the long haul. It’s a relaxed and easy walk that stays right in charming downtown Salem — no hiking boots or broomsticks required.

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.

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.

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.

Historically, Salem isn't known for positive outcomes from chatter, but that's just because there's never been a mouth like Lucinda Lipol's to do the job! While in The Witch City, suppress the urge to buy a tour peddling in shudders and gasps. You can just stay home and turn on Fox News for that. Instead, try having an hour of laughs with Lucinda as she wickedly pokes apart the history of Salem and leaves you wondering if the town will put her to the stake before your next visit. Some say she already has quite the flaming nature. Please understand that due to Lucinda's radically limber mouth, this tour is for ADULTS ONLY and proof of age is required.

When tracing the roots of American independence, the city of Boston is one of the most important epicenters in the country’s history. The Freedom Trail runs through downtown to Charlestown, taking you on a literal walk through the events that inspired and instigated the American Revolution. Join a local guide for a tour of the entire 2.8 mile (4km) trail which includes visits to Bunker Hill and the USS Constitution so you can hear the full historical tale.

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.

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.

Looking for a Salem experience that’s fun for kids without being too scary? This slightly spooky walking tour is designed for kids ages 6 and up, blending intriguing true tales from Salem’s past with mild ghost stories. Follow a quiet, picturesque route just off the busy downtown streets—perfect for avoiding the crowds—before ending at The Witch House., established in 1655.