Massachusetts
Small group

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Our most recommended Massachusetts Small group

Boston: Historic Walking Tour of the Freedom Trail

1. Boston: Historic Walking Tour of the Freedom Trail

Learn about the tumultuous 15-year period that culminated in the American Revolution on this small-group walking tour. As you walk through Boston, you’ll follow the footsteps of colonial Bostonians, all of whom grappled with the difficult question of loyalty or rebellion to crown and country. Start your walking tour on Boston Common, where the Freedom Trail originates. From there, you'll begin your walk along the historic Freedom Trail with your guide. Along the way, learn the significance of landmarks such as the Granary Burying Ground, the Old South Meeting House, the Boston Massacre Site, the Old State House, Faneuil Hall, and more. Your walking tour concludes at either Faneuil Hall (1.5-hour option) or Copp's Hill Terrace (2.5-hour option). The 1.5-hour tour visits 11 of 16 official Freedom Trail landmarks and the 2.5-hour tour includes views of all 16 official landmarks.

From Boston: Quincy, Plymouth, and Mayflower II Day Trip

2. From Boston: Quincy, Plymouth, and Mayflower II Day Trip

Start with a pickup from downtown Boston in a comfortable, air-conditioned, latest model minibus. Travel 30 minutes south to the historic city of Quincy to visit the birthplaces of two former US Presidents, John Adams and his son, John Quincy Adams. Next, enjoy a scenic view of New England's coastline as you travel through Cohasset to the town of Scituate. Once in Scituate, you will have the opportunity to visit the Scituate Lighthouse and hear the amazing story of the "American Army of Two." Then, travel along the beautiful New England coastline towards Plymouth. Visit coastal towns, waterfront mansions, and a lighthouse. Once you arrive in "America's Hometown," visit Plymouth Rock. Benefit from admission to the Mayflower II and Plimoth Patuxet and learn about the site where New England was first established in 1620. Climb back on the bus for a relaxing return trip to Boston.

From Boston: Newport Mansions Full-Day Trip

3. From Boston: Newport Mansions Full-Day Trip

Enjoy Newport on this van tour from Boston. See how the wealthiest families lived during the gilded age with a visit to the Vanderbilt summer home and the Elms Mansion. Along the way, enjoy some complimentary snacks and bottled water while reading over a provided Newport guide book. Begin with hotel pickup in a luxury minibus, where the approximately 2-hour journey to Newport starts. The first stop is the Breakers, the Vanderbilt family's summer home. Take a self-guided audio-tour and explore the 70-room summer cottage. Here, you can also spend some time exploring the cliffs on a scenic cliff walk. Next, it's back to the mini-coach for a bus tour of Newport, which passes St Mary's Parish, where John F. Kennedy and Jacqueline Bouvier were married in 1953. After the bus tour, visit America's oldest existing synagogue, the Touro Synagogue. With your free time, you can do some shopping or have lunch on the waterfront. If you're a sports fan, you can enjoy discount admission to the International Tennis Hall of Fame. Finally, visit the Elms Mansion, where you can take a 90-minute self-guided audio tour. After the tour, return to the minibus, sit back, and relax as you enjoy the ride back to Boston.

Boston: Guided Walking Tour with Seafood Tasting

4. Boston: Guided Walking Tour with Seafood Tasting

Join your guide as you discover Boston's oldest neighborhoods. Learn about the city's colonial and revolutionary history and enjoy some delicious seafood dishes along the way. Your tour begins in Boston's North End neighborhood. Explore the maze of narrows streets and see some of the city's oldest buildings, including the Paul Revere House and Old North Square. Continue your tour as you head to Boston's Harborwalk and Long Wharf to admire the scenic views from the city's oldest commercial port. Learn about the history of Faneuil Hall and the Old State House before you head to Quincy Market. As you tour Boston, stop at three different restaurants for a sit-down tasting of local favorites. End your foodie adventure on a sweet note with dessert from a famous North End bakery.

Boston: Revolutionary Story Walking Tour

5. Boston: Revolutionary Story Walking Tour

Follow the story of the American Revolution chronologically through the streets of Boston on this guided walking tour. Enjoy a tour that places a lot less emphasis on the facts and the dates and a lot more on the passions, personalities, and psychologies driving the events. See historic landmarks where events such as the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill, and the Midnight Ride of Paul Revere occurred. As you walk around, the sightseeing is synchronized with and unfolds to the storytelling. During the tour, begin to connect the characters, moments, and landmarks together, following the story from the settling of Boston to the Declaration of Independence. This tour is designed for the curious visitor who wants to do more than just scratch the surface. 

Boston: Guided Historical City Tour with Pickup & Drop-off

6. Boston: Guided Historical City Tour with Pickup & Drop-off

Immerse yourself in the Revolutionary War with a guided tour of Boston’s historic sites and attractions, with all admission fees and hotel transfers included. Walk the Freedom Trail, visit the Bunker Hill Monument, and enter the USS Constitution with an expert guide by your side. Begin with a downtown Boston hotel pickup in the comfort of a Mercedes Metris van. Kick off the tour with a narrated drive through the city, passing by the Ivy League school Harvard, and the Massachusetts Institute of Technology (MIT). Next, follow your guide to the beginning of the famous Freedom Trail at Bunker Hill Monument, a 221-foot granite obelisk that commemorates one of the first battles in the American Revolutionary War, fought in 1775. Avoid long wait lines with skip-the-line entry. Continue to your final stop of the tour, the USS Constitution, the world's oldest commissioned warship afloat. After admiring this three-masted wooden-hulled beauty, bid farewell to your guide and be taken back to your downtown hotel.

Boston: Guided Night Tour with Sunset Cruise

7. Boston: Guided Night Tour with Sunset Cruise

Step back into the American Revolution and view the very best sites and attractions of Boston on a guided sunset cruise and nighttime walking tour. Join a local expert guide and uncover the story of Boston with historic highlights and personalized recommendations. Begin your tour of Boston with a pickup from your hotel in the downtown area. Kick off your night in Boston with a scenic sunset cruise on Boston Harbor. Relax and take in the breathtaking panoramic views of the city skyline illuminated at night. Next, back on land, your local guide will take you on a narrated walking tour of the North End neighborhood. Stop outside the famous Skinny House, the narrowest house in Boston. See the historic Old North Church, the George Robert Fountain, and the Paul Revere House. You will have the opportunity to grab a quick pastry from Mike's Pastry at the end of your tour. Finally, be returned to your hotel in Boston so you can enjoy the rest of the night.

From Boston: Coastal Maine Small Group Day Trip

8. From Boston: Coastal Maine Small Group Day Trip

Discover Maine’s southern coast on this day trip from Boston and See highlights including York, Kennebunkport, Nubble Light, and the Bush Compound. Soak up stunning sea views and learn about local history and culture. The day begins with pickup from your downtown hotel in Boston and heads towards York, Maine. Upon arrival, stop at the impressive Cape Neddick Light Station, which dates back to 1879. Learn about this iconic landmark and hear how it got its nickname, Nubble Light. From there travel to the town of Ogunquit and enjoy a stroll along Marginal Way. Soak up stunning coastal views and see the Atlantic Ocean beat against the cliffs. End the walk at Perkins Cove, where you can enjoy free time to shop or purchase a ticket for the Lobster Boat Cruise. Arrive at Kennebunkport next and spend a few hours exploring, shopping, and grabbing some lunch. You’ll also enjoy a trolley tour, narrated by a local, and see the impressive Bush Family Compound at Walker’s Point. At the end of an unforgettable day, relax on the return journey to Boston.

Frequently asked questions about Massachusetts Small group

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What people are saying about Massachusetts

The guide was fabulous. Very articulate with an added dramatic flare brought history to life. She very clearly was was an expert in the subject. Would highly recommend her although can’t remember name.

We loved the visit to both the Breakers and the Marbles... and time to do lunch and sightsee Newport. Great day, beautiful weather, and great tour guide/bus driver. He was great!

Informative, well structured, articulate guide. Speaks at level so you learn, not as pedant to impress. So much information will do again on next Boston visit

Great tour! Guide gives the best history lesson you ever received while making it fun. We would even take the tour again. Highly recommend this one!

We had a great tour. Our guide was knowledgeable and interesting! Her presentation was very engaging.