Tour of Boston and Quincy: History and Fun

Planning a visit to Boston? If you’re after a balanced experience that combines history, local flavor, and scenic views, the Boston Bigly Tour might just be your ideal choice. We’ve taken a close look at this seven-hour adventure, and what stands out is the blend of in-depth sightseeing with a touch of fun — all packed into a well-organized, small-group format.

What makes this tour particularly appealing is the value for money — at just $99 per person, it offers an extensive itinerary that takes you from the heart of Boston to the historic hometown of the Adams family in Quincy. The tour wraps in comfort, with cushioned seating, excellent sightlines through large windows, and a professional guide to keep the experience engaging. Plus, the inclusion of a brewery visit and a trip to Quincy adds a layer of depth often missing from standard city tours.

That said, one thing to keep in mind is that the tour is quite full and busy. If you’re someone who prefers a more relaxed pace with plenty of time to explore each site independently, this might feel a bit rushed. However, if you’re eager to pack in as much as possible and enjoy a mix of historical insights and local treats, this tour suits energetic travelers perfectly.

This experience is ideal for history buffs, first-time visitors, or anyone wanting an efficient, fun-filled way to get a big-picture view of Boston and its surrounding area.

Good To Know

• Value-packed: Combines sightseeing, a brewery tour, and visits to Quincy for the price of less than many private tours.
• Comfort and convenience: Small group, air-conditioning, and large windows make for a pleasant ride.
• Rich historical content: From iconic landmarks like Faneuil Hall and the Massachusetts State House to the Adams family homesteads.
• Local flavor: Includes a brewery stop and food options in the Seaport District.
• Time-efficient: 7 hours total, with thoughtfully scheduled stops and brief visits.
• Expert guidance: Knowledgeable, engaging guides enhance the experience.

A Deep Dive into the Itinerary

Starting Point: A Taste of Boston’s Sophisticated Back Bay

The tour kicks off in the elegant Back Bay neighborhood, where you’ll see Copley Square and its landmarks like Trinity Church and the Boston Public Library. These sites immediately set a tone of Boston’s historic affluence and architectural grandeur. We loved the way the guide explained the significance of the buildings, making the early morning city sights come alive.

Shopping and Architecture at Copley Place & Prudential Center

Next, you’ll pass through the upscale Copley Place mall and the Prudential Center. Though it’s primarily a shopping district, the tour offers a glimpse into Boston’s modern prosperity. If shopping is your vibe, you’ll appreciate the extensive selection of over 200 shops, but even for window shoppers, the architecture and views provide a good break from the historical sites.

The Christian Science Plaza Reflection Pool

An iconic piece of Boston’s urban landscape, the reflective pool designed by IM Pei and Associates is a striking example of modern design blending with public space. The guide explained its “Brutalism” style and cultural importance, giving us a fresh perspective on Boston’s architectural diversity.

Fenway Park: Baseball’s Historic Heart

No visit to Boston is complete without a stop at Fenway Park. The guide pointed out the “Teammates” sculpture, featuring legends like Ted Williams. Even if you’re not a baseball fan, the chance to snap a photo outside the oldest stadium in the major leagues adds a nostalgic touch.

The Boston Marathon Finish Line & 2013 Memorial

Passing over the Boston Marathon finish line, you’ll get a moment to reflect on the resilience of the city. The nearby memorial dedicated to the 2013 terrorist attack adds an emotional layer, reminding visitors of Boston’s strength and unity.

Beacon Hill and the Massachusetts State House

Climbing Beacon Hill reveals Boston’s wealth from the 1800s, with beautifully maintained brownstone homes, cobblestone streets, and gas lanterns. The guide’s stories about the history of the State House with its gold-leafed dome brought the area’s political and economic significance to life. The Robert Gould Shaw Memorial and King’s Chapel further deepen your understanding of Boston’s Civil War history and colonial roots.

Historic Landmarks & Benjamin Franklin

Passing the site of the Boston Latin School, where Franklin briefly studied, offers a personal connection to one of America’s most famous founding fathers. The guide shared anecdotes that made Franklin’s Boston origins feel tangible.

The Oldest Building & Boston Massacre Site

Standing in front of Boston’s oldest building and the infamous “Massacre” site, we appreciated the way guides contextualize these moments. The marker about the Boston Massacre reminds visitors of the city’s pivotal role in the fight for independence.

Faneuil Hall: The Cradle of Liberty

Faneuil Hall’s lively history as a speech hub during revolutionary times makes it a must-see. The weathervane and the Hall itself serve as symbols of Boston’s spirited push for liberty. The guide’s storytelling made these historical moments feel vivid.

Quincy & the Adams Historic Sites

Adams National Historical Park

A highlight of the tour is the visit to Quincy’s Adams family homesteads, including the birthplace of John Adams and John Quincy Adams. We loved seeing the sites where these presidents grew up and understanding their significance. The outside photos of Peace Field give a sense of the family’s long-standing influence, even if the interior isn’t open for touring.

A Taste of Quincy’s Presidential Legacy

This stop adds a layer of American political history rarely included in city tours. The fact that these are the oldest presidential birthplace sites in the U.S. makes it especially special for history enthusiasts.

Lunch & Local Flavors at Harpoon Brewery

The tour seamlessly transitions into a relaxed, flavorful experience. The brewery tour is not only informative but also fun — you’ll learn about the brewing process and see how Boston’s colonial beer brewing history continues today. The attached beer hall is a great spot to unwind, whether you opt for a pretzel, pizza, or a local seafood specialty like lobster rolls. Reviewers mentioned that the food was delicious and reasonably priced, making it excellent value.

North End & Paul Revere’s Historic Sites

After lunch, the tour moves through Boston’s North End, famous for its Italian heritage and historic sites like Paul Revere’s House and Old North Church. The guide’s stories made these familiar landmarks even more engaging, especially if you’ve read Longfellow’s poem or are interested in the midnight ride.

Charlestown & Bunker Hill

The final stops are Charlestown, home to the Bunker Hill Monument, and the USS Constitution at the harbor. Visiting “Old Ironsides” grants a glimpse into the navy’s storied past, and the guide’s insights about its victories added context to the impressive vessel.

Transport, Timing, and Group Size

The tour uses private, air-conditioned transportation, which makes the long day comfortable. With a maximum of 25 travelers, the small group structure ensures personalized attention and a more engaging experience. The entire day is well-paced, with about three hours dedicated to transportation, giving you plenty of time to relax and enjoy the scenery.

The tour begins at 8:30 am, a good starting point for a day packed with sights. The schedule includes designated stops with brief periods for photos and exploration, balancing guided insights with free time to absorb each location.

Overall Value and Experience

At $99 per person, this tour offers remarkable value considering the extensive itinerary, expert guides, and inclusions like the brewery tour. The combination of historical sites, local food, and scenic views makes it ideal for those wanting a rundown without the hassle of planning individual visits.

Many reviewers praised the knowledgeable guides, who kept the tour engaging with interesting stories and background details. The comfort of the transportation, especially during Boston’s often unpredictable weather, adds a layer of convenience and enjoyment.

While it’s quite structured and full-day, most found that the variety and depth of experiences justified the pace. If you’re looking for a snapshot of Boston’s past, a taste of local flavor, and some iconic sights all rolled into one day, this tour delivers.

The Sum Up

The Boston Bigly Tour stands out as a solid choice for travelers seeking value, education, and fun. Its unique inclusion of Quincy’s presidential sites and a brewery makes it more than just a city sightseeing trip — it’s a full experience that captures Boston’s historical and cultural essence.

This tour is best suited for history lovers, first-time visitors, and those who want to see a lot without fuss. It’s perfect if you don’t mind a day on the go and want a guided, insightful overview of Boston’s most important sites.

For anyone wanting a well-rounded, affordable, and engaging way to explore Boston and its surroundings, the Boston Bigly Tour ticks all the boxes.

FAQ

Is the tour suitable for all ages?
Yes, most travelers can participate, and the tour’s comfortable transportation and variety of stops make it accessible for families and seniors alike.

How long are the transportation segments?
Approximately 3 hours of the total 7-hour tour involve traveling between sites, providing a relaxed ride with good commentary.

Does the tour include food?
Lunch is not included but is available at the brewery and nearby eateries during the break in the Seaport District.

What is the group size?
The tour accommodates up to 25 travelers, ensuring a small-group feel and personalized guidance.

Are there any additional costs?
Most major attractions like Adams National Historical Park and USS Constitution are free to visit. Lunch and personal souvenirs are separate expenses.

Can I cancel if my plans change?
Yes, free cancellation up to 24 hours in advance, allowing flexibility for your travel plans.

Whether you’re a history buff, a first-timer, or someone eager to learn about Boston’s iconic spots with a local touch, this tour offers a practical and enjoyable way to make the most of your visit.