Best Boston Tours For Every Type Of Vacation

Best Sightseeing Tour – Old Town Trolley Tours

Old Town Trolley Tours has been showcasing Boston to visitors and locals for more than 40 years. With the single largest fleet in the city, you’ll spend less time waiting and more time sightseeing. The friendly and knowledgeable conductors will take you on a fully narrated journey filled with humor and history as you explore the must-see sights of Boston. A really handy component built into this tour is the freedom to hop on and hop off at any of the 18 stops they service.

This means you can take as much time as you like in the historic North End then continue your journey when the next trolley shows up. This pleasant jaunt through American history and the Boston of today includes stops at the Old State House, where patriots would hold fiery debates decrying the oppressors’ back in England, a visit to the oldest floating warship, the U.S.S. Constitution, and a stop at the oldest home in the city where silversmith and Son of Liberty Tom Paine once lived.

Best Ghost Tour – Ghosts & Gravestones

The original “frightseeing” tour had its beginnings in Boston, Massachusetts in 1998 when public interest in the supernatural seemed to be at an all-time high. Since then, this spooky journey through the more sinister and malevolent aspects of Boston’s dark past has been scaring the boots off amateur ghost hunters and curiosity-seekers from all over the country.

Ghosts & Gravestones offers exclusive night-time access to two burying grounds which may include the famed Granary Burying Ground, where legendary Boston patriots John Hancock, Paul Revere, and Samuel Adams are buried and a visit to the King’s Chapel Burying Ground where legend has it many confused spirits still endlessly wander around looking for the graves that were moved after the Revolution. Another tour highlight includes a hair-raising ride past the haunted Omni Parker House considered to be the most haunted hotel in the city. The tour is enhanced by the presence of ‘gravediggers’ that provide narration and a few extra scares for good measure.

Best Neighborhood Tour – Boston Movie Mile Walking Tour

Boston is easily one of the most filmed cities in the United States where some of the most beloved and critically acclaimed films and television shows of all time have been shot. If you’ve ever had the thought, “Wouldn’t it be cool to hunker down on the corner of the Cheers bar where Norm used to sit and have myself a cold one,’ then this tour is what you’ve been looking for!

This unique walking tour of Boston Common and Beacon Hill will guide you through all the places you’ve only seen on screen. You’ll be guided by a local actor who will lead you to over 30 area film and TV locations while giving you behind-the-scenes info about the Boston TV and filming industry.

Best Water Tour – Boston Whale Watching Cruise

Cruise out to the Stellwagen Bank National Marine Sanctuary on a high-speed catamaran in search of humpback and fin whales, harbor porpoises, and Atlantic white-sided dolphins. This high-performance vessel allows you to access the sanctuary in just a half a day. Find a comfortable seat on one of three outdoor decks or inside the climate-controlled cabin and scan the Massachusetts Bay for signs of marine life. During the tour, a naturalist guide will teach you all about the animals’ biology and behavior and answer any questions you may have.

Best Out-Of-Town Tour – Boston to Salem Roundtrip Ferry

Salem, Massachusetts conjures up images of witches and black magic to just about anyone familiar with its place in American history. What is often overlooked, though, is that this was a very important port city where many large clipper ships would trade with the Far East giving rise to the first millionaire in the U.S. Today, Salem is a middle-class commuter suburb of Boston that continues to cast a spell on all those who visit. You’ll arrive there on the 92-foot Nathaniel Bowditch. Expect to see attractions like the House of the Seven Gables, the Salem Witch Trial Museum and the Peabody Essex Museum.

Best Bike Tour – Boston City View Bike Tour

This classic tour is for those looking to get a great comprehensive look at Boston that only a bicycle can offer. You’ll get to know the city and find sites and neighborhoods to explore in great depth. Discover the unique character and charm of each of Boston’s distinct neighborhoods in a fun and intimate way. This is also ideal for those who don’t mind biking on mostly city streets and want to get a little exercise in with their sightseeing. Knowledgeable guides will make sure you’re feeling like a local by tour’s end. Some of the sites on the itinerary are Fenway Park, Boston Commons, Charles River Esplanade, The North End, Trinity Church and much, much more!

Best Walking Tour – Boston Freedom Trail to Copley Square Walking Tour

Head to Boston’s Old State House in the morning to meet your guide. Then, begin your walk along the historic walking path known as Freedom Trail. The route passes many of Boston’s most significant landmarks, from Faneuil Hall to the New State House to the location of the Boston Massacre. Stops include King’s Chapel and the Old Corner Bookstore, and you continue by foot through downtown Boston.

As you wind through the modern skyscrapers, your guide points out important historic sites, such as Boston Common and Boston Public Garden. Before ending your tour at Copley Square, you pass by John Hancock Tower, the Boston Public Library, Trinity Church, and the finish line of the Boston Marathon. Get transported back in time on this guided Boston walking tour through early US history. Stroll along Boston’s Freedom Trail, visiting its most famous landmarks and soaking up the history. Learn about New England’s colonial history and the drama of the American Revolution with the help of a guide.

Best Museum Tour – Boston Tea Party Ships & Museum

Visitors from all over the world travel to Boston, Massachusetts each year to discover the city’s rich history. One of the most popular places to visit is the Boston Tea Party Ships & Museum, an innovative and engaging museum that tells the story of the events leading up to the American Revolution. Located in the heart of the city’s Seaport District, this multi-sensory museum allows visitors to relive history, with interactive exhibits, full-scale restored 18th-century ships, and a fully immersive tour led by a passionate team of historical actors. As part of their commitment to bringing the events of this period into a sharper perspective, there is the opportunity to carouse with colonialists over a spot of tea and re-enact the Boston Tea Party itself!

Best Foodie Tour – Off The Eaten Path

In Boston’s North End, the city’s very own “Little Italy”, your palette will benefit from the dizzying array of culinary creations whose roots lie in the various regions of Italy. This old world neighborhood experience will let you see firsthand what it means to be a “North Ender.” On this tour, you’ll live “La Dolce Vita” and enjoy the art of good eating and good company, Italian style! You’ll be enjoying the best arancini outside of Sicily, cheese and cured meats, homemade pasta, organic wine shop tasting, gelato, artisan bread, and pastries.