Walking Tour of Boston (for 2+)

From: $70   Region: Boston (View all 83 Boston experiences)

This Gift Includes:

  • Free Personalized Gift Pack
  • Buy Now, Book Later
  • Free Returns & Exchanges
  • No Expiration Dates


Boston, MA


Downtown to Back Bay
Daily - 10:00 AM

Downtown, the Waterfront & North End
Wednesdays - 3:00 PM

Harvard Square through Cambridge
Thursdays - 6:00 PM

Boston Jewish Cultural Walking Tour
Mondays - 2:30 PM

Discover Boston by foot on a unique sightseeing tour of Downtown Freedom Trail, Beacon Hill, Back Bay, the Waterfront, North End and Harvard Square.
  • Your fun, local and knowledgeable tour guide will lead you through different areas of Boston where you will hear stories of the city's rich and colorful history
  • Get a behind-the-scenes look at Boston and learn about it's past and present
  • Walking is the best way to see this city where pedestrians are never far from something worth seeing
  • Choose from 4 different tours

More detailed description >

This walking tour will provide you the right mix of history, architecture and culture to bring out Boston's personality and make you feel a part of the city.

The knowledgeable tour guides share their love for the city with facts, stories and humor that reflect the quirky nature that is truly Boston - both in the past and present.

Behold the city's beauty, culture and history from its early beginnings to its striking 19th century architecture, as well as the special charm its unique neighborhoods still hold today.

On any of the tours you choose, you will see the notable landmarks of each district plus youll get to hear some fun facts and stories to make the history around them come alive.

Tour Options:
Downtown Boston to Back Bay via Beacon Hill - Discover Boston's unique charm as you visit dynamic Downtown, journey through Beacon Hill and finish in the beautiful Back Bay.

Downtown, the Waterfront, and the North End - Journey back in time and learn about Boston's original style. See what the early immigrants saw, their first homes in the North End and the shops of Blackstone Block.

Harvard Square Evening Excursion through Cambridge - Travel on America's first subway from Boston Common to the hustle and bustle of Harvard Square in Cambridge on the other side of the Charles River.

Boston Jewish Cultural Walking Tour - Explore Boston's Jewish culture on this tour which includes Beacon Hill's "back side," the Holocaust Memorial, and the West End House.

Key Info >

Essential Information:

  • Moderate walking pace
  • Bottle of water is recommended

2 hours

Maximum Participants:
Up to 20 participants per tour

This experience is only for those on the tour.

Weather Dependent:
Tours run rain or shine. Rain ponchos are usually available from the tour guide in light precipitation. In the event your tour is cancelled due to inclement weather, you will reschedule directly with our experience provider. Always contact the experience provider with any questions regarding weather conditions.

What to Wear:
Wear comfortable walking shoes and appropriate clothing for expected weather.

Booking Information:
For this experience, it is recommended to request bookings at least 7 days in advance.

Cancellation Policy:
Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and have received a booking confirmation, all bookings are final and no cancellations will be allowed. If for some reason you need to reschedule, you can do so up to 72 hours prior to your scheduled date.

Experience ID:

View FAQ's >

  1. How long do the walking tours last?
    Tours last approximately 2 hours, but can vary depending upon the number of people, questions asked, etc.
  2. How far do we actually walk?
    The tours are approximately 1.5 - 2 miles in length.
  3. What are the highlights of the Downtown to Back Bay Tour?
    These are just some of the sites you’ll see: Faneuil Hall, the Old and New State Houses, Boston Massacre Site, the Old and New City Halls, the Old South Meeting House, the Old Corner Bookstore, King’s Chapel, Old Granary Burial Ground, Park Street Church, Boston Common, Beacon Hill, Louisburg Square, Acorn Street, Boston Public Garden, Swan Boats, Cheers, Commonwealth Avenue Mall, Newbury Street, the John Hancock Tower, Boston Public Library, Trinity Church, the Boston Marathon Finish Line, and Copley Square.
  4. What are the highlights of the Downtown, Waterfront and North End Tour?
    These are just some of the sites you’ll see: Faneuil Hall, Quincy Market, Blackstone Block, Holocaust Memorial, America’s Oldest Restaurant, The Boston Stone, America’s Oldest Tavern, The Haymarket, The North End, Boston’s Best Italian Restaurants, The Old North Church, Paul Revere’s House, Boston Harbor, Long Wharf, and The Custom House.
  5. What are the highlights of the Harvard Square through Cambridge Tour?
    These are just some of the sites you’ll see: Park Street, America’s First Subway Station, The Park Street Church, The Longfellow Bridge, Harvard Square, Loeb Drama Center, Harvard Yard, John Harvard Statue, Brattle Street (“Tory Row”), Brattle House, the Longfellow Mansion, Radcliffe Yard.
  6. What are the highlights of the Boston Jewish Cultural Tour?
    These are just some of the sites you'll see: The Milk Street Cafe - a strictly Kosher Oasis in Downtown, The Famine Memorial, Home of The Jewish Advocate, The Jewish "Back Side" of Beacon Hill, Boston's Historic Vilna Shul, The West End House, Puffer House Cigar-Rolling Factory, The Holocaust Memorial, Boston's Immigrant Arrival Area - the North End.
  7. What if I have a particular area of interest?
    If you have a particular area of interest, like history or architecture, please let the guide know and they will likely be able to emphasize that area(s) for the enjoyment of the whole group.
  8. Are there restrooms on the tour?
    There are restrooms at the start of the tour. While there are no prescheduled stops along the way, the experience provider will make every reasonable effort to meet requests for a stop.
  9. Will we be able to purchase water along the way?
    It is recommended to bring a bottle of water along. On most tours, you will pass by street vendors selling drinks. The tour will stop there upon request. Make sure to bring extra cash if you might want to purchase from these vendors!
  10. Will there be food available on the tour?
    No, but there will be restaurants and other food services available where the tour ends. Please have lunch before the we begin, so as to not inconvenience others on the tour by taking time away for you to get something to eat. If a snack is required, you could purchase one from a street vendor when the tour stops for drinks.
  11. Do I need to purchase a ticket for my child?
    Children under the age of 5 may come on the tour for free, but please let us know if you are bringing any young children at the time of booking.
  12. Is the tour stroller accessible?
    Most of the tour is accessible to strollers and we do recommend them for small children. Please keep in mind, however, that many areas are uneven.
  13. Is this tour wheelchair accessible?
    Unfortunately, we do not recommend wheelchairs on these tours because the tours pass through many old, historic areas with brick and cobblestone paving that can be uneven and make travel in a wheelchair difficult. Some tours do include stairways. Please contact Cloud 9 Living prior to booking if you have concerns.
  14. What happens if it rains or snows?
    The tour runs rain or shine. If precipitation starts during the tour, rain ponchos are usually available from the guide. If severe weather forces the tour to cancel, you will be able to reschedule to another date directly with the experience provider.
  15. Does the tour have anything to offer a native Bostonian?
    Absolutely! Boston is full of little known secrets and treasures. Its nooks and crannies provide a wealth of sights and stories that go along with them. The anecdotal history your guide will share with you is sure to add new nuances to what you thought you already knew. You'll see a side of the city you never knew existed!