Top Massachusetts Tours by Duration

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.

Give yourself the best chance of seeing whales in the wild on this half-day boat tour from Gloucester to the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. Once there, look out for humpback and fin whales, plus Atlantic white-sided dolphins and harbor porpoises with the help of a naturalist guide. The on-board galley offers hot meals, snacks and beverages for purchase during the trip.

Learn about Boston’s revolutionary history on a walking tour that emphasizes good storytelling. Enjoy personalized attention from your guide in your small group as you walk a curated route that includes the Freedom Trail. Visit well-known sites as well as more local places and develop an understanding of modern Boston along with its history.

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.

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.

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.

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by a local expert, this 3-hour walking tour features multiple tasting stops with hand-picked seasonal bites from beloved local spots. It’s a delicious way to explore the area, whether it’s your first visit or your summer tradition. Along the way, hear the stories behind the food—tales of tradition, local legends, and the people who make Chatham so special.

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.

Discover two of America’s–and the world’s–most prestigious and historic colleges with exclusive access and a guided tour of each. Explore iconic campus buildings and statues, learn about whimsical traditions passed down through generations of students, learn about key historic moments in both college’s histories, and hear about some of their most famous alumni.

If you have limited time but still want to see all that Martha’s Vineyard has to offer, then book this private sightseeing tour. You’ll pass through the island towns and scenic landmarks with a local guide, who will tell you all about the area, and allow time for plenty of photo stops. You’ll also be driven from place to place in a comfortable, luxury minivan.

If you've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into a Boston city break without using up too much of your time in the city. We pick up in downtown Boston and travel 50 minutes directly to Plymouth. There we'll do a walking tour around the town, explaining why the Pilgrims landed here and how they settled in to the area. Go aboard the Mayflower II (seasonal) to see for yourself how awful their journey must have been and stop by the memorial for the legend of the rock. Quick stop at an impressive monument, built to honor the Pilgrims and then it's back to Boston. Boston is 50 minutes drive from Plymouth, so you will be in the car a chunk of time on this tour. You will have approximately 2 hours in Plymouth.

Visit Martha’s Vineyard on a day trip from Boston to experience the island beauty without the hassle of booking ground and ferry transport. From hotel pickup and drop-off to included ferry tickets, snacks, water, and sightseeing maps, this Martha’s Vineyard excursion is designed for maximum time exploring, with the option to upgrade and include a guided tour of the entire island aboard a high-top, small-group van and explore all six towns on the island, indulge in lunch, and spend more time learning about scenic New England.

See the landmarks and highlights of Boston from the water on this sightseeing cruise in Boston Harbor aboard a 1920s-style yacht. Snap photos and enjoy a unique perspective of the harbor, very different than a typical walking or driving tour through Boston. Highlights include the USS Constitution, Bunker Hill Monument, Old North Church, and the USS Cassin Young.

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

Explore the best of Boston on this hop-on hop-off trolley tour. Board at one of the stops, then hop off wherever you like, explore independently, and get back onto the trolley when you’re ready. Alternatively, ride the 2-hour loop in one go, listening to the informative commentary. Tickets are valid for one or two days, and while admission tickets aren’t included, enjoy discounts to some top Boston attractions.

See all Boston's most important sights in a six hours, private, guided city tour, in a comfortable vehicle. If you value, time, privacy, comfort and would like to have a good overview of the city of Boston, Lexington and Concord at your own convenience and pace, we are the right choice for you. We will drive by or stop and wait at the sights you are most interested in. Our tour is totally customizable and our priority is to please you, not keep a schedule.

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.

Take a semi-private day trip you'll never forget! Start the day with a pickup at your door, then ride up the North Shore to Hammond Castle, located on the ocean cliffs of Gloucester. Take a guided tour of the castle, learning about the history of the eccentric millionaire inventor who built it. Enjoy free time to explore the castle and gardens with plenty of opportunities for stunning photos. Drive to Salem, where you will have free time for lunch. Choose from a wide variety of dining options in the historic downtown. After lunch, your guide will take you on a tour of Salem. Learn about the infamous witch trials of 1692, see the real places where the victims were hanged. Learn the story of the "Corwin Curse" as you take a picture in front of the historic Witch House. See the locations where Hocus Pocus was filmed. Take a drive through one of the most beautiful streets in North America, lined with mansions built on the city's maritime fortune.

While a guided tour is a great way to get to know a city, many try to fit in as many participants as possible. On this small-group tour of Boston, one-on-one time with your guide is guaranteed. Explore the interior of Old Ironsides, the battlegrounds and museum at Bunker Hill, Harvard, and much more on this full-day driving tour dedicated to sharing the hidden history even Bostonians don’t know.

Spend a fascinating day diving deep into the history of Lexington and Concord, and learn all about the role this part of the world had to play in the American Revolution from a local history expert. You’ll travel in a comfortable, air-conditioned vehicle to see Harvard University, Lexington Battle Green, Louisa May Alcott's Orchard House, and enjoy included admission to the Concord Museum with bottled water provided.

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.

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've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened before, during & after the Salem Witch trials - Walking tour of movie scenes, sites and fun facts of Salem - Go into one of the main Salem attractions (entry fee not included, and availability not guaranteed) - 45 minute drive back to Boston If you'd rather skip going into any of the sites, we use that time to take you to Marblehead for some amazing ocean views. The return journey and tour is 4 hours, we're happy to customize it to accomplish the things you're most interested in.