Old Downtown/Waterfront/North End Walking Tour

Boston CityWalks

Zerve Seller: BostonWalks
Activity #1331

Available Dates & Times Price Duration
All times listed are Eastern time zone


Make Boston yours as we explore the beauty and history of Boston’s earliest beginnings that formed the architecture, personality and charm that IS Boston today!

Highlights include:·
  • The North End, Boston’s Italian Area.
  • The beautiful Harbor Area and how it was formed
  • Some of Boston’s oldest architecture
  • The Old North Church and Paul Revere’s House
  • The “hidden” Waterfront Trail
An interesting history of Boston and its architecture, from the time the city was founded in 1630 until today. Learn how Boston’s three hills were used as part of the largest land-fill operation in the world.

See how the first settlers viewed Boston – and who was here to greet them! Some of Boston’s most interesting buildings are seen, including the Old North Church and Paul Revere’s House in Boston’s Italian North End.

Your guide will explain about the Boston Stone in the oldest remaining commercial block in the city. You'll see America's oldest restaurant and America's oldest tavern. You'll walk over the infamous "Big Dig" which now makes up the Rose Kennedy Greenway.

So much to see! At the end of the tour, your guide will be happy to recommend some great Italian North End restaurants or direct you to the New England Aquarium or the Institute of Contemporary Art.

Meeting Location

Near the intersection of State & Congress Streets (Downtown Boston, MA) (Exact meeting location details will be provided immediately upon purchase of tickets.)


10 Reviews Rating: 5 5 out of 5.0
Verified Customer Reviews
Always from real, paying customers
# of Reviews Positive
= Overall
% Positive Average
Last 3 months 1 3 0 = 3 100% 5.0
Last 6 months 1 3 0 = 3 100% 5.0
Last 12 months 1 3 0 = 3 100% 5.0
All 10 28 0 = 28 100% 4.9
10 Reviews
Displaying 1 - 10
Sort by: Date Attended Gender Age Where From Group Type
Rating: 5
Outstanding Tour !
Wed, May 11  3:00 PM Male 50-59 Domestic Tourist(s) Family Without Children
Alan was a terrific guide. He is very enthusiastic and knowledgable.
Rating: 5
Personal and Informative Tour
Wed, Aug 20, 14  3:00 PM Female 40-49 Domestic Tourist(s) Family With Children
We really enjoyed our tour with Allen of Little Italy and surrounding area. Allen was very personable and humorous with a real knowledge of Boston. We were with our 8 year old daughter and she didn't complain once of the the walking or history lesson!

I would highly recommend this tour company. We got a real feeling for the area which helped us for the rest of our stay.
Rating: 5
Interesting and informative
Wed, Oct 30, 13  3:00 PM Female 50-59 Domestic Tourist(s) Individual
Had unforeseen complications during our tour which were handled with creativity and professionalism. An enjoyable experience and well worth the time.
Rating: 5
Enjoyably informative
Wed, May 16, 12  3:00 PM Female 60-69 International Tourist(s) Individual
I was fortunate to be the only person booked on to this walk. The guide was friendly and obviously loved all aspects of his city of Boston and wanted to share it with me. I felt that he tailored the information to fit with my interests and was always willing to answer my questions .At no point did I feel that he was reciting from a prepared text. A thoroughly satisfying and enjoyable experience. I will definitely book another tour with this company on my next visit to Boston.
Rating: 4
Very interesting tour, friendly tour guide
Wed, Jan 4, 12  3:00 PM Male 20-29 International Tourist(s) Couple on a Date
Very good tour at all. We were late and the guide waited for us. The two hours were perfect for the tour, we asked a lot of questions and got a lot of answers. Tour guide was very friendly.
Rating: 5
Fantastic Day
Wed, Dec 14, 11  3:00 PM Female 50-59 Domestic Tourist(s) Individual
Alan was a very informative guide. His love of Boston was quite evident. I would very definitely ask for him again when I return to Boston. I had a GREAT DAY!
Rating: 5
Highly recommend it!
Tue, Sep 6, 11  6:30 PM Male 30-39 Combination Other
Overall I thought Alan was an excellent tour guide! He has spent his whole life in Boston, and was extremely knowledgable about the area- history, architecture, etc.. Was fascinating listening to him, and he was very responsive to our requests. Punctual, friendly, responsive - I thought he was great and would highly recommend him
Rating: 5
Thoroughly enjoyable AND educational.
Wed, May 18, 11  3:00 PM Female 70+ Domestic Tourist(s) Other
My friend and I enjoyed this tour so much. Everything we expected and more.
Rating: 5
Boston Walking Tours
Wed, Sep 22, 10  3:00 PM Female 50-59 International Tourist(s) Unspecified
Our guide Alan provided detailed information regarding the historical sites and also funny stories about some of the places and people of the time period. He also helped us with public transit information which proved very useful.

These walking tours are a great way to get an introduction to Boston instead of walking around on your own with a map not really having a clue about what you are looking at. I also prefer them to the hop on hop off bus tours because we really like the excercise involved, although I would not say they are physically challenging . I would recommend these tours to anyone.
Rating: 5
Great insight into the evolving Boston city scene
Wed, Jul 30, 08  3:00 PM Male 60-69 Local Couple on a Date
My wife and I live in the suburbs and played "tourist" for a day in Boston. We decided to include a guided walking tour instead of just sitting on a Duck boat or wandering around by ourselves. We were glad we did. We were especially interested in getting an up-close look at the new Rose Kennedy Greenway in the post Big Dig era. Alan, our tourguide, was very knowledgable, cordial, and accomodating. His knowledge spanned from American history to modern day "Big Dig" construction, architecture, local politics, and where to eat. Our summer weekday afternoon group was very small, so we had personal treatment. He offered to tailor the itinerary to meet our specific desires at several points along the way.

I've walked around Boston and the Freedom Trail on numerous occasions over the past 40 years, but Alan took us into some locations and told us some facts I never knew before.

We would recommend it highly for active, inquisitive types. You are walking for a couple of hours, so it's not for couch potatoes. We are likely to try another one of his tours in the future.
Displaying 1 - 10 of 10
Ratings and Reviews for:
Is advance purchase necessary?
You must purchase your tickets in advance in order to guarantee your space on the tour. Please book well in advance to maximize your chances of getting the date and time you prefer.
How long do the walking tours last?
Tours last approximately 2 hours, but can vary depending upon the number of people, questions asked, etc.
How far do we actually walk?
This tour is approximately 1.5 miles in length.
Do we walk at a leisurely pace?
Yes, tours move at a leisurely place. Though at times we might move faster because there is so much to see and talk about, we do stop frequently and we promise not to overwork you!! We try whenever possible to stop in the shade when it's hot and in the sun when it's cool. And where there are benches, we'll point them out.
What specific Historic Sites will we see?
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.
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.
Are there restrooms on the tour?
There are restrooms at the start of the tour. While there are no prescheduled stops along the way, we will make every reasonable effort to meet requests for a stop.
Will we be able to purchase water along the way?
On most tours, we will pass by street vendors selling drinks. We will stop there upon request. Make sure to bring extra cash if you might want to purchase from these vendors!
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 that we don't 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 we stop for drinks.
Can we do shopping along the way?
While the tour does pass through shopping areas, we request that you save all shopping until after the tour has finished. At the conclusion of the tour, we will be happy to give you directions to get back to specific shops and locations.
Can I ask questions?
YES!!! Questions are always welcome.
Do I need to purchase a ticket for my child?
Yes, please purchase a reduced price Child ticket for children ages 5 to 16. 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 when you purchase your tickets. Remember to bring a stroller!
Will my toddler survive the tour?
Well, it's a long way for a toddler to go, so I can't recommend it. But you know your child best - if you think they'll enjoy it and they'll behave, go ahead and bring 'em along. We'll try and make it as pleasant as we can for both you and them.
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.
Is this tour wheelchair accessible?
We pass through many old, historic areas with brick and cobblestone paving that can be uneven and make travel in a wheelchair difficult, but doable.
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 really severe weather forces us to cancel the tour, you will be able to reschedule to another date or receive credit for a future event.
How do I get back to my hotel after the tour?
Your guide will give you specific directions following the tour. If either walking or taking the "T" subway are possibilities, your guide will describe both options for you. Maps will be provided upon request.
Where does the tour end?
This tour ends at the very tip of Long Wharf. It is one of the most beautiful spots in the city, as it juts out into the Harbor looking towards Logan Airport, making you feel like you're in the ocean (but you don't get wet!!). It's truly a wondrous sight.
What are the differences between the offered tours?
The North End, Waterfront and Downtown Tour includes the original settled area of Boston and then proceeds to the North End and winds up on the Waterfront. This historic tour that goes beyond where the others leave off. It includes Paul Revere's House, the Old North Church, Boston's Italian Area and the oldest commercial block in the city. If you want to sneak in some Italian food, you might want to consider that, too. The Downtown Boston to Back Bay and the Back Bay to Downtown Tours cover many of the same sites. The first, as its name indicates, leaves from Downtown and the second from Copley Square in the Back Bay, so you can choose based on which starting point is closest to your hotel or which time offered best meets your needs. The Harvard Square Evening Excursion goes to the lovely town of Cambridge, so is very different than our other tours. You'll learn about its history and see the interesting architecture of Harvard Square and Harvard University.
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!
Are gift certificates available?
Of course. You can reach Boston CityWalks with the "Contact BostonWalks" link.
Are private tours available for Boston CityWalks Tours?
We would love to create just the right tour for you or your group. Please click on the "Contact BostonWalks" link to make arrangements!


Boston CityWalks

Boston CityWalks gives just the right mix of history, architecture and culture to bring Boston’s personality alive and make you feel a part of the city. We share our love for the city with facts, stories and humor that reflect the quirky nature that IS Boston.

The Downtown, Waterfront and North End Boston WalkingTour gives us a chance to show you Boston's original style. We can relate to you what it was like at Boston's birth, what the early immigrants saw, their first homes in the North End and the shops of the Blackstone Block.

Boston CityWalks also does customized tours to your specifications. These personalized walking tours are perfect for weddings, engagement parties, birthdays, anniversaries, reunions, and other special events.
Please call Zerve at
1 (800) 979-3370
to get more information or
book this activity now
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