Private tour in Boston Joshua L

The North End and Freedom Trail Walking Tour

4.9

(43) reviews

-
Hours icon 3 hours
Walking
Private tour for 1-8 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 3 hours
Walking
Private tour for 1-8 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

Joshua L.

4.9

Guide rating

136

Reviews

Tours delivered

3 hrs

Avg. response time

It would be my pleasure to welcome you to Boston, the perfect walking city! I grew up here, and I love my hometown for its fascinating history and incredible beauty. I'm passionate about introducing visitors to everything from our classic spots to the hidden gems of Boston, Cambridge, Salem, Lexington, Concord, Plymouth, and beyond! Professionally, I am a designer of extraordinary educational experiences — in addition to tour guiding in the Boston area, I have worked as a teacher and facilitator, actor and theatre director, historical interpreter, international trip leader, and am currently an instructional designer at a local university. I have a master's degree in theatre and education, and my storytelling savvy makes Boston's history and culture come alive! I am also a fluent Spanish speaker, having been a Fulbright Fellow in Colombia, and led travel and exchange programs across Latin America and Asia for high school and college students. I am happy to deliver any of my tours in Spanish or English. I'm immersed in Boston's vibrant arts and culture scene. I perform improv comedy and sing in a choir. I enjoy introducing visitors to the abundant cultural offerings here, from theatre and music to visual arts and dance. I also love the Red Sox, but I won't hold it against any of you Yankees fans out there…my dad is from New York, after all! I love meeting people from all over the world customizing my tours to fit my clients' interests. Here are a few examples of bespoke tours that I've recently given: •A tour focusing on Jewish Boston from colonial times through the present day •A ghost tour focusing on haunted local spots, alluringly bizarre legends, and true crime •A tour for a celebrated podcast focused on abolitionists and poets along the Black Heritage Trail in Beacon Hill •A tour in Spanish for Argentine physicians focused on scientific and medical innovations •A recorded tour series around Harvard and Cambridge for the iFit's Immersive Global Workouts As a tour guide, I love revealing the rich layers of history and illuminating architectural masterpieces that exist along the Freedom Trail and beyond. -From Native Americans to Puritans and witches in the 1600s -Revolutionaries and Sons of Liberty in the colonial 1700s -Civil War heroes, literary superstars, and globetrotting sailors in the 1800s -Mobsters, Kennedys, and Boston Brahmins in the 1900s -Boston's sports successes and futuristic advances in science and technology coming out of Harvard and MIT in the 2000s Literally anyplace that you stand in this dynamic city has fascinating stories to tell. The foodie scene is also tremendous! I relish (my jokes are usually better than that, I swear!:) introducing visitors to the deliciousness that abounds here, from classics like waterfront lobster rolls and heirloom apple cider at farmers markets, to unique tastes like shakshuka at innovative boutique cafes and pastries at the best Italian bakeries hidden down back alleys in the North End. Another of my favorite things to do as a tour guide is create customized adventures around the region, from Boston and Cambridge walking tours to excursions out to fascinating historic and scenic spots like coastal Salem and the North Shore; Plymouth; Lexington and Concord; architectural gems like the Boston Public Library; universities like Harvard and MIT; and places where nature's beauty shines, like gorgeous Mt. Auburn Cemetery or Arnold Arboretum. I also enjoy curating guided visits to our extraordinary museums, featuring one-of-a-kind treasures of art, history, archaeology, and science. Popular ones include the Isabella Stewart Gardner, the MFA, and the Harvard Museum of Natural History. I connect really well with everyone from seniors to families with kids, and clients tell me that my passion and excitement is contagious! If you're also curious about the world around you, love a good story and a good laugh, and get excited about delicious food, we'll definitely enjoy each other's company. I look forward to helping you craft your dream Boston area experience! • MA, Emerson College- Education and Theatre • BA, Vassar College • Fulbright Fellow, Colombia • Certificate in Spanish, Universidad de Buenos Aires, Argentina • While Boston doesn't offer tour guide licensure, I have given hundreds of private concierge tours throughout the Greater Boston area for a local boutique tour guiding company specializing in customized experiences for a diverse range of clients I am not a commercially licensed driver. If you wish to take a driving tour, I can either accompany you as a passenger in your personal or rented vehicle, or we can hire an insured car and driver from a local chauffeur service.

Have a question or want to customize this tour? Message Joshua L.

Overview of your Boston tour

Step into the heart of history- "the room where it happened" from the 1600s through today! This scenic walk brings the richness of my hometown's past to life, from Puritans running wild to radical revolutionaries, pirate curses, and an epic flood of molasses. Meet mobsters, Kennedys, and Sons of Liberty in the pub where they planned the American Revolution. Visit Paul Revere's house (1680) and the iconic Old North Church (1723), from which Revere began his midnight ride in 1775, walking the same cobblestones as the founding fathers. See grand architecture, from the State House's golden dome astride Beacon Hill, to a grasshopper flying above Faneuil Hall since 1742. Taste local delicacies from secret Italian bakeries tucked away down back alleys, and meet the generations of Irish, Jewish, and Italian immigrants who built this City on a Hill. This tour is completely customizable to your interests- tell me what excites you, from history and literature to food and wine, and we'll make that our focus.

Your Boston tour itinerary

There are days worth of stories and sights along the Freedom Trial, so we'll focus on what you're most interested in! Classic stops on this customizable itinerary include: Boston Common Beacon Hill Massachusetts State House (welcomes visitors weekdays 9-5) Boston Athenaeum Omni Parker House Granary Burying Ground (Samuel Adams, Paul Revere, John Hancock) Old City Hall- Ben Franklin and Latin School King's Chapel Old South Meeting House- Boston Tea Party Old State House- Boston Massacre City Hall Plaza Faneuil Hall/Quincy Market Holocaust Memorial Boston Public Market/Haymarket Union Oyster House/Green Dragon Tavern Kennedy Greenway/Big Dig Hanover St. /Little Italy Bakeries and Pastry Shops Wharves and Waterfront Paul Revere House Rose Fitzgerald Kennedy Birthplace Revere Bells/St. Stephen's Church Old North Church Copp's Hill Burying Ground Salem St. foodie gems- Polcari's/Regina's/Bova's North End waterfront views out to Charlestown USS Constitution Charlestown Navy Yard Bunker Hill Monument

Want to customize this tour?

Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.

Transport details
Type: Walking

This is a walking tour. Downtown Boston is compact- some call it the perfect walking city! If you'd like, we can also take the ferry from Long Wharf to Charlestown, which is a beautiful way to see Boston Harbor from the water!

What's included
Other: -Fantastic stories and laughs -Beautiful photos -Answers to all of your questions about where to eat, drink, see theatre, hear music, catch sports games, be wowed at museums and by nature in the Greater Boston Area and New England
Private Guide
What's not included
Other: Personal expenses. -Local snacks aren't included in the price of the walking tour...but are definitely worth trying! -Entrance fees to any museums along the route that you should desire to visit aren't included- some people are inspired to do so in the moment; always a fun addition to the experience, but I can also tell you what you'll see inside, and you can go back later if you wish!
Food Drinks Snacks
Meeting location

Boston, Massachusetts, United States

We can begin wherever is most convenient for you. If you don't have a preference, I generally suggest meeting on the Boston Common.

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
History
City Highlights
Food And Drink
Tour reference number
540604
Languages
English
Spanish
Activity level
Light
Accessibility
Kid Friendly
Wheelchair Accessible
4.9

Traveller reviews for this private tour in Boston

43 reviews

Frequently asked questions

Who is this private tour in Boston best suited for?

This private tour in Boston is perfect for history enthusiasts, food lovers, and anyone interested in exploring the rich cultural tapestry of the city. It's also ideal for families, as it's kid-friendly and wheelchair accessible. Whether you're a first-time visitor or someone looking to delve deeper into Boston's past, this tour offers a personalized experience that can be tailored to your interests.

What should I bring or wear?

Can this private tour in Boston be customized to focus on what I want to see and skip places I've already visited?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

Is transportation included?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What languages is this tour offered in?

What's included in this private tour, and what should I budget for separately?

Is this a private tour? What is the maximum group size and the starting price?

AI-generated. Please confirm details with your guide

-
Hours icon 3 hours
Walking
Private tour for 1-8 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 3 hours
Walking
Private tour for 1-8 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
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