Boston Sightseeing Tours — Local services in Boston

TLDR; If you're looking for a tour of Boston that feels thoughtful, fun, and full of personality - especially if you're traveling solo and want to feel like you're part of something - this is the one. Ask for Crafty as your tour guide if possible! At $47 per person, the Summer Nights (pm) tour is an incredible deal to see the city on wheels and on a boat on the Charles River. (Not sponsored or incentivized)

I recently took the Boston Sightseeing Summer Nights Tour, and I can't recommend it enough! It was genuinely one of the highlights of my trip. This was my first time exploring a new city alone, and I left the tour feeling included, energized, and connected - something I didn't expect but deeply appreciated.

From the moment we boarded the bus, there was an atmosphere of warmth and fun. Our guide, Crafty, was incredible! He wore so many hats - driver, historian, DJ, trivia master, and all-around entertainer. He had the dad jokes, the fun facts, the city history, and perfectly timed music. His energy made the whole bus feel like a community, not just a group of strangers. I've been on tours that felt rushed or disconnected, and this was the opposite.

Huge perk: Unlike some other Boston tours, this one gives you a full hour on the Charles River. I was originally going to do a Duck Boats tour, just because it's so heavily advertised, but those tours were sold out (and I came to find out give you only 20 mins or so on the river).

Here's what you can expect: Your tour guide (I hope it's Crafty) takes you on a ride through the city with trivia, stories, and photo ops You get dropped off for a boat ride on the Charles River - the boat tour was equally impressive, because the bartender was also the guide! He was mixing drinks and giving detailed commentary on the architecture and history. The boat has bathrooms, bar with drinks and snacks, open views for amazing pictures of the city

At around $47 per person, I thought this was an incredible deal. I would expect something this engaging and well-organized...

Our tour of The Freedom Trail and Boston’s North End could not have been better. Neal’s knowledge of Boston and its history, his sense of humor, and sincere desire to deliver a bespoke experience ensured a truly memorable day for me and my wife, and our best friends, two other couples who accompanied us.

Neal was great to work with both in the planning and execution of the tour. He provided great feedback on all the things I hoped to experience in our four hours with him, and offered excellent suggestions along the way, including a truly special lunch at Ben Cotto in the North End. He also helped us put together our Great Cannoli Taste Off, in which Mike’s won over Modern by the slimmest of margins.

It's also worth noting that Neal went out of his way to connect with each of us, smartly adapting his style to accommodate the unique chemistry of our group. This included patiently waiting as we took yet one more ‘groupfie’ in front of some other landmark, monument, or headstone. His many years as a teacher served him and us well, especially since four of us came out of different areas of education. He did a wonderful job keeping us focused and moving, without the day ever feeling rushed.

In the end, I appreciated that Neal felt much more like a fellow traveler, who enjoyed the opportunity to share with his friends the many, many things that he was proud of in his hometown. During our time together, we saw much that we had learned about when we were students, as well as much that was unique about the city, that only a resident would know of. This included a bit of the grittier and dare I say occasionally salacious details that make for great anecdotes when sharing our experience with others.

I and my besties have traveled a good bit, in different parts of the world, and I like to think we know excellence when we experience it. So, returning to my days in academia, I would unreservedly give Neal an A+, and would wholeheartedly recommend him for your next...

I highly recommend Neal as your guide for exploring Boston. My son (23 yr), his roommate, his roommate’s mom, and I visited Boston for a long weekend in November (all first-time visitors to Boston except for me). Neal made great recommendations during the planning that helped us pick the best use of our time and the limited time stuck in traffic. On the tour day, he conveniently picked up and dropped off at our hotel. Neal, a former teacher and Boston native, was well-prepared with a binder filled with maps, pictures, and articles, allowing us to absorb large amounts of information during the ~3-hour tour. His knowledge of the city's history, paired with his colorful storytelling, provided an enjoyable and helpful overview that helped us select spots to explore in detail later on our own. He infused the tour with anecdotes and humor seamlessly into the narrative (poking fun at the Boston accent “Hahvahd” where the “Wicked Smaaht” students go to school as we visited that area). If you’re looking for a knowledgeable and personable guide to discover Boston, Neal is an...