Signing up for a tour of a new city is one of the best ways to learn about the area and even meet other travelers. All tours are fantastic, whether you book a bus tour, bike tour, Segway tour, walking tour, etc. That’s because you get a chance to explore beautiful and historic cities with the benefit of a knowledgeable and enthusiastic guide.

But, when it comes to walking, there are certain undeniable pluses. For example, you don’t have to worry about scoring a window seat, you don’t have to stop to secure a bike or Segway when you want to switch it up and explore on foot. Plus, you get some steps in while you are busy learning.

In this post, we will show you three cities that are especially great for walking tours in the Northeast region. For each city, we provide a “Top Choice” an “Honorable Mention” and a “Runner Up.” 

Some Tour Tips

1. Take the tour as early in your visit as possible. This helps you quickly learn the city’s layout. In addition, your tour guide will help point out places you’ll want to try to see (or revisit) before you leave town.

2. Show up a few minutes early. Most guides are excellent at ensuring everyone hears the scripted parts of the tour. Nonetheless, you stand a better chance of learning more about places in between stops if you are walking closest to the guide and can banter a bit.

Portland, Maine

Wine Wise (Top Choice)

It’s not often that a tour is so incredible that people book the tour first THEN start looking for accommodations, but that’s what sommelier Erica Archer has accomplished with Wine Wise. Billed as “more than just a wine education, a wine experience”, Wine Wise offers wine (and food) walks in Portland, Kennebunk, Kennebunkport and Ogunquit. Erica learned about wine from the masters, including Karen MacNeil – author of The Wine Bible, and Tim Gaiser – nationally renowned wine expert. She loves sharing her passion for wine and it shows — her tours sell out quickly. Private events and sunset sailing tours are also popular choices.

Historical Walking Tour, Maine Historical Society (Honorable Mention)

A stroll through Portland is memorable for the architecture alone. Building architect John Calvin Stevens and landscape architect Frederick Law Olmsted, Jr. left considerable impressions on the city. The Maine Historical Society holds daily guided tours highlighting Portland’s history, maritime heritage and authentic character.

Popular topics are famous city residents, historic landmarks, social history and the Great Fire of 1866. Tours are offered daily, June – October (weather permitting) and are 60-75 minutes long. Limited to 12 guests (first-come, first-served). Admission: $15 Walking Tour only, $25 Walking Tour & Wadsworth-Longfellow House Tour Combo. Free for children six years old and younger, but tour is recommended for ages 12 and older. 

Wicked Walking Tours (Runner Up)

The hallowed cobblestone streets and 19th century buildings of Portland’s waterfront are teeming with haunting secrets and tales of mystery. Led by a comic actor and international opera singer, this locally owned, award-winning tour brings the people and streets of Portland to life. As one reviewer said, “You don’t need to believe in ghosts to enjoy the ghost stories.” Fun for all ages. Tours are 70 minutes long, 1/2 mile in length and often sell out.


Providence, Rhode Island

Providence, Rhode Island

Providence Tours by Deena (Top Choice)

The guide makes the tour. And Deena, like many places along the tour route is a national treasure. She brings the past to life while providing a great perspective on Providence’s resurgence. As one reviewer put it, she is an “excellent guide that clearly loves her city.” Providence has some gorgeous areas to walk to, Federal Hill, Benefit Street, and College Hill, which was named #4 most beautiful neighborhoods in America in 2015 by Thrillist. 

Providence Ghost Tour (Runner Up)

Take a guided tour by lantern light through the East Side of Providence, an historic neighborhood that got its start in the 1630s (back in the days of Roger Williams himself). Many of the houses in this part of Providence date back to before the Revolution. The old saying “if walls could talk” may not apply here. The staff has thoroughly researched state archives and other resources to unearth evidence of paranormal activities in the area. While you may not see ghosts, the tales shared on the tour just may raise the hair on the back of your neck! Tickets are $18 per adult. Please see the website regarding whether the tour may or may not be appropriate for your children. 

Boston, Massachusetts

Pink Tulips and Statue in Boston's Public Gardens

Black Heritage Trail® (Top Choice)

Lesser known than Boston’s renowned Freedom Trail, Black Heritage Tours, led by National Park Service staff offer a highly informative look at the history of the 19th century African American community of Boston. Each roughly 90 minute tour, led by a National Park Service Ranger, leads visitors through the Beacon Hill neighborhood that is steeped in both the history of Boston’s 19th century African American community and is where many important milestones in the abolitionist movement occurred. Tours are Free and occur frequently (often daily) from spring through late fall. 

Off the Eaten Path (Honorable Mention)

Boston’s North End is packed with restaurants and specialty food shops and there’s no better way to experience it than with a guide who is passionate about food and knows the landscape. The stated mission of Off the Eaten Path is to “have fun, learn and taste some good food.” From this participant’s point of view, it’s a five star experience. Save room for the cannoli! As an added bonus, you’ll make brief stops at Paul Revere’s House, the Old North Church and other landmarks. Tours leave from North Square (across from Paul Revere’s House) Monday through Saturday at 11:00 a.m. rain or shine and are limited to twelve people. The tour lasts 2.5 hours. Tickets are $60 per adult plus tax (children under 12 are half-price). 

Bites of Boston (Runner Up)

This aptly named tour serves up interesting nuggets of historical information about Boston’s fascinating South End neighborhood with stops at 6 eateries along the way to enjoy fresh seafood, chef-inspired sandwiches and fresh baked chocolate chip cookies. Not a full course history tour nor a seven-course foodie tour, many find this 3 hour, 2 mile tour provides the right balance of each.