The 9 2-Hour Experiences in Boston Worth Booking Ahead

1.2-Hour Beacon Hill True Crime Expert Guided Tour

★★★★★★★★★★5.0 · 182 reviews · 2 hours (approx.) · from $35Our pick

At 7 pm, join a true crime guide for a two-hour walk from the Massachusetts State House through Beacon Hill’s back streets and alleys, ending across from Massachusetts General Hospital. Guides have included Tony, Andy, Spencer, and Cady. Expect historic crime stories, time for questions, and a group capped at 15.

“We had a lot of fun on our Beacon Hill "True Crime" Tour with Andrew! The stories were fascinating, and just the right amount of spooky yet funny and interesting – a perfect mix of history and intrigue that kept everyone interested. Walking through the charming streets of Beacon Hill at night made it all feel so immersive and fun.Our guide Andrew was outstanding – knowledgeable and an incredible storyteller. What really stood out was how well the tour worked for our family group: we had our 12- and 14-year-old kids plus my 80-year-old in-laws, and everyone loved it equally. Highly recommend this tour – it's a unique and entertaining…”

Check availability →Read our full review

2.2 Hour North End ‘Little Italy’ Walking Tour

★★★★★★★★★★4.5 · 125 reviews · 2 hours (approx.) · from $35

Start at the Tony DeMarco Statue at 12:30 pm for a guided walk through Boston’s North End. You’ll hear about local history and famous residents, visit food shops and landmarks, and finish near Polcari’s Coffee. Guides have included Tony, Andy, and Cady. Food and drinks cost extra.

“We had a great time learning the history and enjoying some great food! We went back to several of the places we visited during the rest of our trip.”

Check availability →Read our full review

3.2-Hour Historic Walking Tour

★★★★★★★★★★4.7 · 88 reviews · from $45

Follow a guide from the Old State House area through Boston’s historic center, Beacon Hill, the Back Bay, and Copley Square. You’ll see landmarks including Faneuil Hall, Louisburg Square, Trinity Church, and the Boston Marathon finish line while hearing local stories and historical context. The two-hour tour costs $45 per person and is usually offered in the morning.

“We had an amazing time on this tour! Our guide, Alan, was fantastic—engaging, knowledgeable, and full of fascinating stories that brought Boston’s history to life. The two-hour walk flew by as we explored Beacon Hill, Back Bay, and the Freedom Trail, learning both well-known facts and hidden gems about the city. Alan had a great sense of humor and made the experience interactive and fun. Whether you're a history buff or just visiting Boston for the first time, this tour is a must. Highly recommend!”

Check availability →Read our full review

4.2 Hour Boston Segway Tour

★★★★★★★★★★5.0 · 77 reviews · 2 hours 30 minutes (approx.) · from $99

Ride a Segway with a guide through Boston’s waterfront, North End, Charlestown, Beacon Hill, and downtown. Expect a safety briefing and time to learn the controls before setting off, plus short stops at landmarks such as the USS Constitution, Bunker Hill Monument, and Boston Common. Guides named by past participants include Captain Jay, Rick, Rob, and Thompson.

“Never been on a Segway before but this experience was awesome. Captain Rick knocked our experience out of the ball park. Highly recommend!!!”

Check availability →Read our full review

5.2 Hour Boston Historical and Heritage Walking Tour

★★★★★★★★★★4.5 · 70 reviews · 2 hours (approx.) · from $5Best value

Walk about a mile from Boston Common to Faneuil Hall with an English-speaking guide, often Stephen, who connects famous Boston sites with lesser-known stories about abolitionists, revolutionaries, writers, and city politics. The tour costs $5, runs about two hours, and covers a lot of history at a brisk pace, with time to ask questions along the way.

“Stephen was very knowledgeable on a wide variety of related topics. I would highly recommend this tour with him! Awesome experience!”

Check availability →Read our full review

6.2 Hour Historic Pub Crawl in Boston

★★★★★★★★★★5.0 · 45 reviews · 2 hours (approx.) · from $35

Start at Faneuil Hall Marketplace at 6:30 pm, then visit historic Boston taverns including the Green Dragon and Dirty Nelly’s. Your guide shares pub and beer history as you go; drinks cost extra, and the tour ends at Bell in Hand, billed as America’s oldest tavern. Groups are capped at 15.

“Cady was a great tour guide and host. Fun experience with a great balance between Boston history and fun pub crawl.”

Check availability →Read our full review

7.Sail Away: Explore Maine’s Coastal Beauty on a 2-Hour Excursion

★★★★★★★★★★5.0 · 42 reviews · 2 hours (approx.) · from $139

Join a small-group, two-hour boat trip from Saco to see the Saco River, Wood Island Lighthouse, Saco Bay islands, Old Orchard Beach, and Biddeford Pool. The group is limited to six, and the crew may include Captain Bob, Chloe, or Jake. Cold bottled water and safety equipment are provided; blankets are available if needed.

“Captain Bon and Chloe were amazing. Boat is beautiful and they are very knowledgeable about sailing and the history of the lighthouses and islands. It’s a must do.”

Check availability →Read our full review

8.2-Hour Historical Walking Tour

★★★★★★★★★★4.9 · 36 reviews · 2h 30m · from $49

Walk from Dock Square along Maine Street and nearby lanes, hearing how shipbuilding changed Kennebunkport and learning about the people behind its old homes. The English-language tour is limited to nine people, lasts up to 150 minutes, and ends near Union Square with a local sweet treat. Guides have included Beth, Cynthia, Julie, Marlene, and Barbara.

“Cynthia was very informative and thorough. Pace of tour was very good.”

Check availability →Read our full review

9.Freedom Trail: Small Group or Private 2 Hour Walking Tour

★★★★★★★★★★4.1 · 5 reviews · 2 hours · from $20

Walk Boston’s historic downtown and North End with an English-speaking guide on a two-hour private tour for up to two people. Hear why the Tea Party mattered, weigh the events of 5 March 1770, and learn how Paul Revere and Boston’s printers helped spread revolutionary ideas. Recent guides have included Chad, Tressa, and John.

“Tressa was very friendly and knowledgeable. She brought the stories to life. Highly recommend this tour for history buffs and novices alike.”

Check availability →Read our full review