I love history. For many years, I acquainted myself with cities by reading about their past, then exploring them by myself (mostly on foot). But in recent years, I’ve started taking advantage of more structured walking tours as part of my experience. Here are a few things I’ve learned about walking tours that I always keep in mind:

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.

I’ve picked out three cities to feature in this blog. For each city I provide a “Top Choice” an “Honorable Mention” and a “Runner Up.” I hope you get a chance to explore these beautiful and historic cities with the benefit of a knowledgeable and enthusiastic guide.

Portland, Maine

Portland, Maine Town

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.) Call 207-619-4630 or visit their website.

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 1 – October 12, at 1:30 PM (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. Call 207-774-1922 x212 or read more online.

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. Call 888-718-4253 or visit the website.

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. As one reviewer put it, she is an “excellent guide that clearly loves her city.” Providence has some gorgeous areas to walk, Federal Hill, Benefit Street and College Hill (named #4 most beautiful neighborhood in America in 2015 by Thrillist) and Deena brings the past to life while providing a great perspective on Providence’s resurgence. Call 401-944-5134 or go to the website.

Savoring Rhode Island (Honorable Mention)

Federal Hill has far more than terrific architecture going for it. Since the late 1800s, it has been the epicenter of culture and business for Providence’s Italian population. The restaurants and shops in this part of town are simply incredible. Certified executive pastry chef, author and educator Cynthia J. Salvato leads exquisite tours through Federal Hill’s traditional and modern bakeries, wine shops and specialty food shops, where you can sample the tremendous flavors and get free Italian cooking advice along the way. Tours start promptly at 9:00 a.m. and last approximately three hours. Cost is $50 per adult (Christmas and Easter tours are $55). Not appropriate for children under 12 years of age. Tour size is limited to 14. Call 401-934-2149 or visit the website for more info.

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. Call 401-484-8687 or visit the website.

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. Call 617-742-5415 or visit the website.

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). Call 617-504-8813 or visit the website.

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. Call 617-477-0567 or visit the website.