Top 13 Historical Tours in Boston

1.Freedom Trail History Small Group Walking Tour

★★★★★★★★★★5.0 · 6,450 reviews · 2 hours 30 minutes (approx.) · from $35Our pick

Walk Boston’s full Freedom Trail with a historian guide and up to 15 other people. Over 2.5 hours, you’ll connect Boston Common, the Granary Burying Ground, Faneuil Hall, Paul Revere’s North End, and more to the tense years before the American Revolution. Indoor warm-up breaks may help in cold weather.

“Our travel guide Alejandro was knowledgeable and enthusiastic in his depiction of each historical destination. He was sympathetic to the frigid cold temperatures and we had warm-up breaks, which were appreciated. His overall presentation was educational and informative to even the Boston resident!”

Check availability →Read our full review

2.Tour of Historic Fenway Park, America’s Most Beloved Ballpark

★★★★★★★★★★4.5 · 3,013 reviews · 1 hour (approx.) · from $45

Spend an hour inside Fenway Park with guides such as Steve, Matt, Jack, or Mary Ella, visiting the Green Monster, roof deck, Pesky’s Pole, and Living Museum. You’ll hear Red Sox stories, see rare memorabilia, and gain access to areas usually closed during a game.

“Fantastic experience, large group, toured the entire stadium from one side to the other, guide was great!”

Check availability →Read our full review

3.Boston Food & History: Pizza, North End & Freedom Trail

★★★★★★★★★★5.0 · 1,772 reviews · 5 hours (approx.) · from $90

Join guides such as Nabil, Lexie, Bob, or Claire for a five-hour Boston walk linking North End food with Revolutionary-era sights. You’ll sample bread, pizza, an Italian sandwich, coffee, and a pastry, then walk about five miles from the harbor to Boston Public Garden.

“We had a great time with Olivia, even though it was raining so much we were all soaked by the end. Olivia kept us in high spirits with all her stories and her welcoming personality. The food was delicious. Highly recommend!”

Check availability →Read our full review

4.City Cruises Historical Sightseeing Cruise

★★★★★★★★★★4.6 · 1,771 reviews · 1 hour · from $46

Cruise from Long Wharf around Boston Harbor for one hour with live English narration. You will pass the USS Constitution, Bunker Hill Monument, Old North Church, Castle Island, and the harbor islands, with open-air decks, large-window seating, and snacks for sale.

“We had a wonderful time and our caption was funny and easy to listen to during the tour.”

Check availability →Read our full review

5.Freedom Trail History Small Group Walking Tour

★★★★★★★★★★4.9 · 1,590 reviews · 2h 30m · from $35

Follow Boston’s Freedom Trail for 2.5 hours with an English-speaking guide such as Maura, Nick, or Alejandro. See 16 official landmarks, hear lesser-known Revolutionary stories, pause at Quincy Market, and finish near the Old North Church with views of the USS Constitution and Bunker Hill Monument.

“Candace was lovely. So knowledgeable and friendly. Really enjoyed”

Check availability →Read our full review

6.City Cruises Boston Historic Sightseeing Harbor Cruise

★★★★★★★★★★4.5 · 1,388 reviews · 1 hour (approx.) · from $46

Cruise Boston Harbor for an hour with live narration about the Revolutionary War, Boston Light, Old Ironsides, and the working port. Guides such as Kevin, Holly, and Mike have been praised for lively storytelling. You get indoor and outdoor seating, skyline views, and snacks for purchase.

“Sit on the upper deck on the left side for best views. Tour guide gave a good overview of the harbor. He did have a bit of an attitude. The woman lining everybody up to board was excellent - gave us great tips to enjoy the cruise. She should have given the tour.”

Check availability →Read our full review

7.Boston’s North End Food Tour: Italian Flavors & Heritage Walk

★★★★★★★★★★5.0 · 1,322 reviews · 2 hours (approx.) · from $70

Walk about 1.3 miles from the Greenway Carousel into Boston’s North End, stopping for fresh bread, Italian meats and cheese, pizza, pastry, and coffee. A local guide such as Lexie, Nabil, Olivia, or Bob adds Paul Revere stories and neighborhood context. The group is capped at 12.

“Our tour guide was very knowledgeable on the content on the area. Took us to great food spots to sample delicious options. We had a great time. We even got great spots to sample afterwards.”

Check availability →Read our full review

8.Boston Pizza Lovers Food and History Walking Food Tour

★★★★★★★★★★4.5 · 1,082 reviews · 2 hours 50 minutes (approx.) · from $69

Walk Boston’s North End for about 2 hours 50 minutes with guides such as Scotty or Big Al. Taste three full-size pizza slices, hear stories about Paul Revere and Old North Church, see Old Ironsides and Bunker Hill, then finish with a cannoli from Modern Pastry.

“Alvin was a great guide with tremendous enthusiasm, a warm manner and a great command of local history.”

Check availability →Read our full review

9.Delicious Donuts of Boston: A Sweet History Walking Tour

★★★★★★★★★★5.0 · 1,038 reviews · 2 hours (approx.) · from $70

Spend about two hours walking from Kane’s Donuts to Boston’s North End, tasting artisanal donuts, apple cider donuts, Boston cream, and Union Square favorites. Guides such as Jackie, Lucy, Katie, and Stephanie add local stories about the Greenway, Quincy Market, and Boston’s donut culture.

“my coworkers and I had a great time! Lucy was so personable and very knowledgeable/ passionate about donuts!”

Check availability →Read our full review

10.Boston Freedom Trail History Pub Crawl Small-Group Tour

★★★★★★★★★★5.0 · 996 reviews · 2 hours 15 minutes (approx.) · from $60

Meet at the Samuel Adams statue outside Faneuil Hall for a 2-hour-15-minute walk through Boston’s Freedom Trail pub scene. A local guide such as Maddie, Julie, Sam, or Anna leads you to four nearby bars, sharing history and drink tips. Drinks are purchased separately.

“This tour guide was great but the tour was just a pub crawl. You'll see hi-lights were disappointing. Not much of a tour.”

Check availability →Read our full review

11.Boston City View Bicycle Tour: History and Landmarks

★★★★★★★★★★5.0 · 638 reviews · 2 hours 30 minutes (approx.) · from $78

Ride about 8 to 11 miles through six Boston neighborhoods on a comfort hybrid bike or optional pedal-assist e-bike. Your guide leads you past Fenway Park, the North End, Beacon Hill, the Esplanade, Copley Square, and Boston Common, with frequent stops for history and photos.

“Great way to explore different areas of the city while getting pieces of information along the way. Easy ride - anyone who can ride a bike can do it with no problems.”

Check availability →Read our full review

12.Boston History Tour: Scenic Walk Through Time & Landmarks

★★★★★★★★★★5.0 · 627 reviews · 2 hours (approx.) · from $39

Follow a local guide from the Greenway Carousel through Faneuil Hall, Old State House, Boston Common, Beacon Hill, and the Public Garden. In about two hours and 4 km, you’ll hear Revolutionary stories, spot overlooked landmarks, enjoy a local treat, and get practical Boston tips.

“The diversity of knowledge Alan our guide had made the tour special. He was conversant on history, art, architecture and much more. Combined with a good sense of humor, he made our tour memorable.”

Check availability →Read our full review

13.Boston’s North End Food and History Walking Tour

★★★★★★★★★★5.0 · 459 reviews · 3 hours (approx.)

Join Paula of Off The Eaten Path Tours for a small-group walk through Boston’s North End. Taste arancini, Sicilian pizza, cheese, prosciutto, pasta, wine, cannoli, gelato, and espresso while learning how the neighborhood became Boston’s Italian heart.

“So much interesting history in the North End, and the little hidden spots for delicious Italian treats!! Paula is a long time resident of the North End and it is very apparent that she loves it!! She, herself, is a treasure!!”

Check availability →Read our full review