Top Massachusetts Sightseeing Tours in 2026

Boston’s architectural history is spread across several neighborhoods—this small-group walking tour links Back Bay, the Public Garden, and Beacon Hill with commentary from a Boston guide with 20+ years of experience. See landmarks including Copley Square, the Swan Boats, and Acorn Street, while practical smartphone photo tips help you capture the city without taking a technical photography class.

Enjoy a gourmet brunch on this scenic cruise of the Boston Harbor. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with eggs, bacon, fresh fruit, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Sea Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.

Explore the best of Boston's Freedom Trail—and get more out of the visit than you could if exploring on your own—on this guided walking tour that covers many of the city's most important sights. Wander cobblestone streets, check out the historic architecture, and learn about the colorful past of this dynamic destination. Stops include Faneuil Hall, King's Chapel, Boston Common, and more.

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features a meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night, or head to the dance floor for music and fun in the ship’s nightclub.

See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.

Explore Newport in a single day without planning or driving from Boston. This small-group tour includes pre-booked mansion admissions, guided transport with hotel pickup, and free time in the historic waterfront district to help you use your time efficiently. Visit iconic mansions, enjoy a scenic coastal walk, and discover additional historic landmarks along the way. With logistics handled in advance, you can focus on architecture, scenery, and independent exploring.

Join us for our Secrets of Salem Dark History tour--right in the heart of Witch City! You might be surprised to learn that Salem has a name that contradicts its image. The colonists chose the name Salem, which is the Hebrew word for peace, for the town in the seventeenth century. Salem, Massachusetts, was a significant American colonial town and a seaside hamlet with a maritime history. It exhibits many of the characteristics we identify with those early settlers, such as a Puritan work ethic, devotion to education, strong links to the community, and a hardiness to weather the rigors of a coastal winter. Of course, Salem is inextricably associated to witches and the 1692 witch trials. Join our Salem History Experience and discover everything there is to know about Salem, the witch trials, and beyond.

Travel back in time, to the early years of the United States of America, during this guided walking tour of Boston’s Freedom Trail and beyond. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses, and visit the setting of the infamous Boston Massacre. Then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square.

Uncover the dark past and mysterious legends of Salem on this haunted history walking tour. Expert historians and paranormal investigators help separate fact from fiction while retelling the events of the 1692 witch trials and leading you through Salem’s most notorious sites. Escape the gimmicks and delve into authentic tales of voodoo, witchcraft, vampires, and ghost sightings that have left their mark on the infamous New England town.

Boston CityPASS® — Planning a trip to Boston? Save 45% on admission to four must-see attractions. Experience Boston’s must-see tourist attractions — and enjoy considerable savings — on this exciting Boston CityPASS. Choose four admissions between the following seven attractions: New England Aquarium, Museum of Science, Boston Harbor City Cruises, View Boston Observation Deck, Franklin Park Zoo, or Harvard Museum of Natural History This Boston CityPASS is valid for 9 consecutive days from date of first use. Convenient mobile tickets are valid for 1 year from the date of purchase. Transportation to and from the attractions is not included.

Explore elegant neighborhoods, historic streets, and American landmarks on a Boston walking tour from the Back Bay to Beacon Hill and downtown portions of the Freedom Trail. Learn about Boston’s history and culture as you stroll brownstone-lined avenues and walk the shady paths of the Boston Public Garden. Step into Boston’s Revolutionary history in the churches, cemeteries, and battlegrounds of the American struggle for independence.

Discover Boston’s North End—one of the city's most historic neighborhoods, and now home to its Little Italy—on a photography walking tour designed for small groups. Immerse yourself in the vibrant atmosphere, and visit iconic Freedom Trail sights including Paul Revere’s House and the Old North Church, plus hidden gems off the beaten path. Bring your camera for expert photography tips, perfect for all skill levels.

Cover a lot of ground and get a better understanding of the city of Boston with this private driving tour. In the company of your guide, walk the Freedom Trail and learn about the history of the city. Travel in an air-conditioned vehicle to easily see part of the city beyond the historic center.

Upgrade your drive through scenic Cape Cod with this private self-guided tour you can download onto your phone. The audio narration plays based on your location, letting you start, stop, and skip stops whenever you like. You control your time and pace, enjoying a personalized experience without the constraints of traditional tours.

Discover the stories behind historic Boston sites on a self-guided tour of downtown, and enjoy the flexibility to experience the city on your own schedule. Booking this tour means access to audio guides that never expire, so you can explore as much—or as little—as you want at a time. The included GPS-enabled app gives turn-by-turn directions as expert tour guides narrate revolutionary history and more.

Cover the highlights of the Freedom Trail on this walking tour of Downtown Boston. A shorter route leading between Boston Common and Faneuil Hall Marketplace is ideal for travelers who don’t have the time or inclination to cover the full extended route. A costumed guide adds a theatrical touch to the experience.

With its centuries of history, it’s no surprise Boston is packed with haunted sights, though they aren’t always easy for visitors to find. On this nighttime ghost tour, follow a guide to some of the city’s most storied landmarks, such as the Granary Burying Ground, Bostom Common, and the Massachusetts State House, and discover the hidden history and spooky sightings associated with each.

Seeing the best of Boston doesn’t get any easier, or more economical, than with Go City's Boston All-Inclusive Pass. This flexible sightseeing pass allows visitors to pick and choose from a wide variety of Boston’s top things to do, at any pace desired over the course of one, two, three, five, or seven consecutive days. Simply save the pass (available as your 'ticket' after purchase) on your mobile device and go. No voucher redemption is required.

Discover the spooky stories behind Boston’s historic places on a self-guided walking tour that lets you explore at your own pace. Turn-by-turn directions lead you through the streets of Boston, from the Boston Athenaeum to the Central Burying Ground, while a narrator shares theatrical tales from the city’s past. Choosing a self-guided tour means experiencing the city on your own terms, with more flexibility than a group excursion offers.

Discover Boston’s rich past and vibrant present on this small-group (or private) walking tour—a relaxed and informative way to get your bearings if visiting the city for the first time. Gain valuable insight from local guide as you explore spots such as Boston Harbor, Faneuil Hall, Beacon Hill, and the Public Garden. As you wander, learn about the city’s Revolutionary roots, architectural gems, and cultural evolution—and get an understanding of what life is like for modern-day residents.

Discover some of Boston's most notable historic landmarks—and pair your sightseeing with a pizza crawl—on this time-saving, two-in-one walking tour. With just a guide and small group for company, stroll through the city’s oldest neighborhoods, including Little Italy on the North End. Walk along the Freedom Trail to sights including Paul Revere House and the USS Constitution, and head to local pizzerias for three full-size slices along the way.

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic ferry crossing, historic seaside villages, and the laid-back charm of island life. Board the Island Queen ferry in Falmouth and cruise across Nantucket Sound to Oak Bluffs, where colorful gingerbread cottages surround the historic Tabernacle at the Martha's Vineyard Camp Meeting Association. Enjoy time to explore the island's most iconic spots, with an optional sightseeing bus tour covering the Flying Horses Carousel, the refined harbor town of Edgartown, Gay Head Light atop the dramatic Aquinnah cliffs, and Nobska Point Lighthouse. Return via the Steamship Authority ferry from Woods Hole, rounding out a full day of coastal views, ocean breezes, and authentic New England island character.

Enjoy Boston from the water while dining on a delicious buffet lunch on this cruise. See an array of top landmarks including Bunker Hill, the World Trade Center, and the site of the 1773 Boston Tea Party. After lunch, head up to the top deck—the largest outdoor patio deck in town.

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.