Guided tour

Boston History & Highlights Afternoon Tour

Guided tour

Boston History & Highlights Afternoon Tour

Save up to 20%

From US$ 49 US$ 39.20 per person


Go beyond the Freedom Trail and experience modern Boston through the city’s incredible history. From the iconic Boston Harbor, to the famous Freedom Trail, into the heart of beautiful Beacon Hill.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 2 hours
Check availability to see starting times.
Live tour guide


  • Enjoy a fun-filled journey on and off Boston’s famous Freedom Trail with a local
  • Learn the modern impact of Boston’s most iconic historic sights
  • Explore inside some of the sights overlooked by many visitors (and even locals)
  • Take in Beacon Hill's red-brick architecture on a shared group or private tour
  • Join a carbon neutral tour, organized and led by an eco-certified tour operator
Full description

Begin at the lifeblood of Boston, the Boston Harbor, with a walk through a scenic waterfront park, with views of the harbor. From the harbor, continue past the Rose Kennedy Greenway, State Street, and the historic Custom House Tower, the city’s first skyscraper.

Then, your guide will lead you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views. Moving into the heart of Downtown Boston, stop in front of the Old State House and the site of the Boston Massacre. Was it really a massacre or maybe just great propaganda for the Revolution? Ask your expert guide about that one!  A short trek through Downtown Crossing brings you to Old City Hall. This beautiful building, done in French Revivalist architecture, was the seat of city government for years in Boston. It also happens to be the site of the birth of public education in America. You'll definitely want to have your guide snap your picture with the bronze donkey outside the entrance.

On most weekdays, you’ll have a chance to see the government at work (or not) inside the inspiring, historic and beautiful Massachusetts State House, designed and built by famous federalist architect Charles Bulfinch in 1798. Outside the State House, take in the views of modern Boston, including the skyscrapers of Downtown, the Financial District, and the tallest building in New England: the John Hancock Tower.   Continue your journey through Beacon Hill, where you’ll have a chance to take in the quintessential architecture of Boston’s red brick row houses. Get out your cameras — this neighborhood is one of the most photogenic in the city.

Finally, arrive at the beautiful Boston Public Garden, one of Boston’s favorite green spaces, where you’ll see locals walking the dogs, playing with the kids, and enjoying lunch in the shade. Your guide will point you in the right direction, and will help with any and all recommendations for great things to do in Boston that evening and beyond. 

  • Local English-speaking guide
  • A surprise local treat
  • Additional food and drinks
  • Tips for your guide

Select participants and date



Meeting point

Meet at the Greenway Carousel, next to the Carousel entrance.

Open in Google Maps ⟶
Important information

Know before you go

  • This tour is organized and led by the world's largest travel B-Corp certified company. B Corp Certification measures a company’s social and environmental impacts and responsible tourism practices
  • Entrance to the Massachusetts State House requires a government ID, and all guests must pass through metal detectors. The State House is open on weekdays only, and you will have alternate sites to visit on weekends.
  • In the event of a site closure, the supplier will do their best to replace it with a similar alternative.
  • This is a child-friendly tour. Children between the ages of 6 and 11 inclusively are permitted on this tour at the rate listed above. Please select ‘child’ above when booking. Children under the age of 6 are permitted to join this tour free of charge. Please inform the supplier at the time of booking if you’ll be bringing a child under the age of 6.
  • For your Urban Adventure you will be in a small group of a maximum of 12 people.
Customer reviews

Overall rating

4.8 /5

based on 87 reviews

Review summary

  • Guide
  • Value for money
  • Service
  • Organization

Sort by:

Traveler type:

Star rating:

Great tour, great guide, great value for money. The perfect way to see Boston in just a few short hours. Bob (the guide), really knew his stuff and made the tour fun and interactive. He also provided some suggestions of other places to visit during our weekend which was greatly received. I would certainly recommend this tour.

March 25, 2023

Bob Hornstein, our tour guide was excellent. His tour was informative and filled with "fun facts" beyond the normal tour experience. I particularly liked how he summarized the tour highlights in an email after the tour ... and even added his suggestions for restaurants to visit. Overall, I would say the tour experience was excellent!

March 25, 2023

Our guide, Bob, was awesome. A very knowledgeable Bostonian, he shared insightful and interesting stories about the city’s past. We chose a 16 degree day for this tour but Bob made sure to sneak in some “inside” history in order for us to thaw our frozen hands and toes! Highly recommend Bob and this tour!

March 25, 2023

Product ID: 161796