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, join your local guide on an experience that promises to connect you to the Boston of old and new.
Boston History & Highlights Discovery Tour
- Join your local guide for a fun-filled journey on and off Boston’s famous Freedom Trail
- Learn the modern impact of Boston’s most iconic historic sights
- Explore some of the sights overlooked by many Boston visitors (and even locals!)
- Take in the beauty of the architecture and quaintness of Beacon Hill
- Enjoy a surprise local treat with your guide.
Your experience begins at the Aquarium “T” Station on the historic Long Wharf, the focus of Boston Harbor, and the economic engine of Boston for most of its history. From the harbor, we’ll 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, we will stop in front of the Old State House and 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 (government hours only!) you have a chance to see the government at work 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. We continue our 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, we 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 drink
- Tips/gratuities for your guide
Cancellation Cutoff: 24 hours
Cancellation Notes: Up to 24 hours before the beginning of the activity: full refund Less than 24 hours before the beginning of the activity or no-show: no refund
<div>Your Trip: For your Urban Adventure you will be in a small group of a maximum of 16 people. <br><br>Confirmation of booking: If you have your voucher, your booking is confirmed. We'll see you at the start point. Get in touch if you have any concerns or require more information via the email address or phone number (business hours only) on your voucher. <br><br>Child Policy: 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. Children under the age of 6 are permitted to join this tour free of charge. Please inform us at the time of booking if you’ll be bringing a child under the age of 6. </div>
- Duration: 2 hours
- Trip difficulty: Easy
- Category: Tours & Sightseeing



