The Best Boston Sightseeing Tours To Take In 2025

Planning on making a trip to Boston and want to see it all? I’ve handpicked the best Boston sightseeing tours that you can take this year to get the most of my hometown.

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Looking For The Best Boston Sightseeing Tours?

You’ve definitely come to the right place! I’ve lived in Massachusetts my entire life, and I’ve taken more Boston sightseeing tours than I can count.

I’ve been on amazing whale watches in Massachusetts, taken the absolute best Boston food tours around, seen every inch of the Freedom Trail, been up close and personal with Fenway Park, and more.

I can tell you if Boston is worth visiting (ummm, YES), and when the best time to visit Boston is. I’ve even crafted the perfect one day in Boston itineraries catering to different interests. Like I said, I’m an expert on Boston.

Don’t have time to read this whole article?

Book this Food & Freedom tour now. It gives you the best of Boston’s history and food!

Every single one of these Boston sightseeing tours is sure to give you an incredible experience. It doesn’t matter if you’re looking for interesting historical Boston tours, or leisurely harbor cruise tours – all of these tours are worth taking.

I know I have them numbered, but that doesn’t mean I think tour number 8 is worse than tour number 3. I’m just listing all the best sightseeing tours in Boston, in no particular order. They’re all fantastic, believe me!

Ready To Book The Best Boston Sightseeing Tours?

There are quite a few different types of sightseeing tours in Boston that you can take. Trolley tours are a popular option, along with walking tours.

There are also boat tours, driving tours, and (one of my favorites) the hybrid Duck Boat tours. You can take a bike tour, or even head up to Salem for the best Salem Witch Trial tours around.

So, let’s get into these Boston sightseeing tours so you can pick your favorite and start experiencing my wicked awesome city!

Expert Tip: A lot of these tours are small-group tours – meaning they have limited availability and spots fill up quick. Book online in advance to guarantee your spot!

My Top 3 Picks For Boston Sightseeing Tours

#1 Top Pick

Food & Freedom Tour

⭐️⭐️⭐️⭐️⭐️

• Freedom Trail
• North End
• Rich History
• Delicious Food

BOOK IT

#2 Pick

Hop-On Hop-Off Trolley Tour

⭐️⭐️⭐️⭐️⭐️

• Expert Guides
• At Your Own Pace
• All Top Boston Sites

BOOK IT

#3 Pick

Duck Boat Tour

⭐️⭐️⭐️⭐️⭐️

• Land and Sea
• Charles River Views
• Top Boston Sites

BOOK IT

#1. From Food To Freedom Tour

Rating: 5 Stars | Tour Length: 5 hours | Check Rates And Availability

First up on my list of the best Boston sightseeing tours is this North End Food & Freedom Trail tour. It mixes Boston’s delicious food with cool stories from the past all wrapped up in one awesome adventure.

Starting at Boston Harbor, you walk along the water before heading into the historic North End, known for its incredible Italian food. Your guide shows you cool places like a cute Italian bakery and a real Italian deli.

After you’ve had some snacks, it’s time to check out the famous Freedom Trail with your guide. You see historical spots like the Old North Church and where the Boston Massacre happened, all while enjoying local treats like pizza and Italian desserts.

Whether you love learning about history or just love good food, this Food & Freedom Trail tour gives you a taste of Boston’s past and present. It’s not just about history; it’s about trying new foods and having fun, so trust me, you’ll enjoy every moment of it.

#2. Hop-On Hop-Off Trolley Tour

Rating: 4 and 1/2 Stars | Tour Length: 2-8 hours | Check Rates And Availability

Old Town Trolley Tours is an incredible option for sightseeing in Boston. Your ticket allows you unlimited reboarding all day long, so you really can see Boston at your own pace.

The trolley takes you to all the most popular spots in Boston, including Faneuil Hall, Boston Common, the Back Bay, and more. You also get discounted tickets to other tours and attractions as well.

This Hop On Hop Off Trolley Tour is a fantastic way to see everything in Boston. You can even opt for the 2-day ticket so you really can explore the entire city. It’s easily one of the best Boston sightseeing tours available!

#3. Duck Boat Tour

Rating: 4 and 1/2 Stars | Tour Length: 1 and 1/2 hours | Check Rates And Availability

One of my absolute favorite Boston sightseeing tours is the Duck Boats! These are amphibious vehicles that give you the best of Boston’s land and sea.

You start off cruising by iconic Boston landmarks like the Boston Commons and the TD Garden, and then you splash down into the Charles for a leisurely river tour! You get to see the beauty of Boston from a whole new angle and it’s incredible.

What makes the Duck Boat tours even more special (as if they weren’t unique enough already), are the tour guides. Your ConDUCKtor® infuses history with humor, ensuring you not only learn fascinating facts but also have a blast along the way.

#4. Fenway Park Tour

Rating: 4 and 1/2 Stars | Tour Length: 1 hour | Check Rates And Availability

Fenway Park has and always will have a special place in my heart – it’s where my husband took me on our first date way back when our love story started! If you can’t get to a Red Sox game, you’ve got to take a Fenway Park tour instead.

You learn about the most famous ball players, see thousands of wicked cool artifacts and photographs, and even get to stand on top of the Green Monster. Depending on the day and what else is happening at Fenway, you might be able to go into the dugouts or even on the field itself.

You get incredible views of Fenway and the Boston skyline during your Fenway Park tour. The history you learn about is absolutely fascinating, and it’s definitely a tour worth taking while you’re in Boston.

#5. Historic Sightseeing Cruise

Rating: 4 and 1/2 Stars | Tour Length: 1 hour | Check Rates And Availability

Since Boston is located on the coast, there are some historical sites that are best viewed by boat. This awesome historical sightseeing cruise gives you expert commentary as you sail around the Harbor.

You get to see amazing spots like America’s oldest continuously manned lighthouse, get up close and personal with the USS Constitution, see the expertly restored Boston Tea Party ships, and more.

I love harbor cruises, and just being on the water in general. For sure this historical Boston Harbor cruise is a great choice to see Boston from another perspective. Plus the commentary gives you a great mix of interesting facts with a few laughs mixed in.

#6. Best of Boston Small Group Tour w/Boat Cruise

Rating: 4 and 1/2 Stars | Tour Length: 5 hours | Check Rates And Availability

I love tours that give you lots of value, and this small group Best of Boston tour certainly does that. First off, the groups are capped at 7 people, which means lots of personalized attention throughout your tour.

Second, you get to see the best of Boston’s landmarks like the Bunker Hill Monument and Quincy Market. And finally, you also get to see historical Boston sites by boat! You see the USS Constitution and the location where the Boston Tea Party took place all while taking a relaxing cruise around Boston Harbor.

If you want a way to see the best of Boston by land and sea, this Boston van and boat tour is the way to go. You see a lot, learn a lot, and the guides really make it fun and interesting.

#7. Private Boston Sightseeing Driving Tour

Rating: 5 Stars | Tour Length: 3 hours | Check Rates And Availability

Private tours are one of my favorite ways to really get a customized, personal tour of a city. This private driving tour in Boston is incredible at showing you all the best spots in Boston at a pace that works for you, not just for a big group.

You see iconic spots like Paul Revere’s house, Faneuil Hall, and Fenway Park, of course. But you also get to visit various neighborhoods in Boston. You see the Back Bay and Beacon Hill, among others. It’s really a great and thorough guided tour.

If you’ve ever been to Boston before, you know you don’t want to drive here yourself. I’ve lived here my whole life and still don’t want to drive in the city! This private guided driving tour takes the stress out of exploring by having a local expert show you around instead.

#8. Boston Historic Taverns Tour W/Ferry

Rating: 4 and 1/2 Stars | Tour Length: 3 and 1/2 hours | Check Rates And Availability

Any tour that combines history and sightseeing with delicious food and drinks is my kind of tour. This historic tavern tour includes stopping in a couple pubs, having delicious snacks and beverages, and gives you an incredible understanding of Boston’s revolutionary history.

You get to explore different neighborhoods around Boston while learning interesting facts about the history and culture. Plus, you get to eat yummy foods, like a cannoli in the North End (affectionately known as Little Italy). You’ll see the Old North Church, the Bunker Hill Monument, and more.

Another reason why this Boston historical tavern tour is on my list of the best Boston sightseeing tours is that you also get to take a round trip ferry ride. There’s nothing quite like seeing Boston from the Harbor, and you won’t regret taking this tour.

#9. Boston Seafood Lovers Food & History Walking Tour

Rating: 5 Stars | Tour Length: 2 and 1/2 hours | Check Rates And Availability

Boston’s right on the coast, and one of the things we’re famous for is our amazing seafood. This fantastic seafood and Boston history tour gives you a chance to try some of our most iconic dishes while learning interesting facts about the city.

Clam chowder and lobster rolls are two of the most well-known Boston classics and you can try them both, along with other treats like raw oysters, and finish them off with a delicious cannoli in the North End. Along with the yummy foods you also walk parts of the Freedom Trail, and stroll along the Harbor.

Food is the way to my heart, so this seafood lover’s history tour is easily one of the best Boston sightseeing tours available. The combination of fresh local seafood coupled with interesting facts and tidbits about Boston really make this tour special and definitely worth taking.

#10. Boston City View Bicycle Tour

Rating: 5 Stars | Tour Length: About 3 hours | Check Rates And Availability

If you like riding a bike, this Urban AdvenTours bicycle tour of Boston is for you! You get to see all the beauty of Boston, including neighborhoods such as the Back Bay, Southie, and Charlestown.

You stop in Copley, the heart of the Back Bay. Here you get to see Trinity Church, the Boston Public Library, and the finish line for the Boston Marathon. You also stop in the gorgeous Boston gardens, where you can see the famous Make Way For Ducklings sculptures, the Swan Boats, and all the beautiful lush greenery.

A guided bicycle ride through Boston is definitely one of the best sightseeing tours in Boston you can take. What better way to enjoy nature, learn history, and get exercise all at once!

Final Thoughts On Boston Sightseeing Tours

I’ve explored my fair share of cities, but as a Boston native, this city will always hold a special place in my heart. But are Boston sightseeing tours worth it? YES. These tours promise to make your visit unforgettable.

Whether you’re a local or a first-time visitor, each of these sightseeing tours in Boston offer a unique journey through the heart of the city, ensuring that your time in my hometown is everything you wanted and more.

I featured the 10 best Boston sightseeing tours in this article, but if you still can’t decide, let me help you make that choice!

Still can’t decide?

I suggest this Food & Freedom tour. It’s a 5-star tour that gives you the best of Boston’s history and food!

There are tons of ways to see Boston, but I’ve always been a fan of guided tours, no matter what city I’m in. There’s just no better way to get to know a city than by spending time with an experienced local.

No matter which of these Boston sightseeing tours you choose, it’s always a good idea to have on comfortable shoes, perhaps bring an umbrella, and remember sunscreen.