There are many ways to get around Boston, birthplace of the Duck Tours and home to the Big Dig, Swan Boats and the T. But the best approach to getting to know this city intimately is on foot. Whatever your interests—chocolate, history, ecology—these guided Boston walking tours have an enlightening path for you to follow.
Boston Food Tours | bostonfoodtours.com
Somewhere between Kelly’s Fried Clams and Legal Sea Foods, Boston is teeming with ethnic enclaves. Michele Topor’s Boston Food Tours focuses on two: Chinatown and the North End. On the Chinatown Market Tour, your guide will help you discover the city’s best moon cakes, barbecued meats and even a Chinese herbal pharmacy. After two and a half hours of tasting, you’ll top off the afternoon with a dim sum lunch. No trip to Boston is complete without a walk through Boston’s “Little Italy,” the North End. For three hours, your North End Market guide will lead you to some of the country’s best marzipan and cannoli, and act as your cooking and buying guide through salumerias and the greenmarket.
Boston Food Tours are 3 hours and cost $50-65 plus tax. Learn more and book your ticket (required) here.
Boston by Foot Tours | bostonbyfoot.org
Boston by Foot offers both topical and neighborhood-themed tours. There’s something for everyone, including “Boston By Little Feet” tours geared towards children. Want to explore Charles Bulfinch’s early American architecture, the narrow streets and brownstones behind the State House’s golden dome? Check out the Beacon Hill Tour. Ready to walk in the footsteps of literary giants like Ralph Waldo Emerson, Nathaniel Hawthorne, Henry David Thoreau and Louisa May Alcott? Take a Literary Tour through Victorian Boston. Get a deeper look at the epic Big Dig on “Boston Underfoot” or see “Where Boston Began” in Charleston. Choose a “Green Tour” for a stroll through beautiful open spaces like Rose Fitzgerald Kennedy Greenway, a green highway that will host the Art Zestival on May 19 and 20 this June.
Most Boston by Foot Tours are 1.5 hours and $12 per adult ($8 for children). Check their site for schedules and more information.
Freedom! Self-Guided Tours | nps.gov
If groups and guides aren’t your style, why not lead yourself? Outside of Boston proper, the bus and T-accessible Brookline is one of the city’s most culturally rich areas. The Brookline Historical Society created a neighborhood tour that takes readers from the eighteenth century Devotion House museum and North Brookline’s farming roots, to schoolhouses and estates, the town’s oldest Jewish synagogue and finally John F. Kennedy’s birthplace.
Marked by a red line, the Freedom Trail starts at the Boston Common and winds through sixteen official stops including the Old Corner Book Store, Boston Massacre site, Faneuil Hall, Paul Revere House and Bunker Hill Monument. The trail ends at the USS Constitution, where free guided tours await.
The City of Boston also provides free iPod tours of the Harborwalk, Fort Point Channel and the Public Garden.
Free guided tours available every half hour from 9:30-3:30. Entry for self-guided tours 4-5pm only. Check site for updates on hours and seasonal closings and directions. Don’t forget to take along a copy of the Brookline Historical Society’s neighborhood walk and/or inquire about free neighborhood tours at the JFK NHS.
Read up on the Freedom Trail on the Freedom Trail Foundation’s user-friendly site.
Boston Chocolate Tours | bostonchocolatetours.com
Forget “save the best for last.” This 14-person walking tour is all about enjoying dessert first. Check your guilt at the door as you sample all kinds of artisan sweets (even soups!) from champagne truffles to wine and chocolate pairings. Choose from six different areas to tour, including Beacon Hill, Harvard Square, and Faneuil Hall, and feel good about burning off the bon-bon calories in between stops on this two and a half hour edible adventure. Get educated by Boston’s top chocolate producers about their craft and leave with exotic recipes, baking tips, treats, and a new appreciation for the finer (heart-friendly!) foods in life.
Boston Chocolate Tours tickets cost $48 per person.
How to get there: Consult oM’s Boston Transportation Guide
Photos: Boston Chocolate Tour
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
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Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram