Top Boston Walking & Biking Tours

From Food to Freedom Trail Walking Tour

• 1 Review
• Combine two attractions Boston has to offer - delicious food and rich history - on this tour that starts in the popular North End and  then continues along the Freedom Trail. Snack your way through this historic Italian neighborhood, trying fresh bread at a hidden bakery and enjoying an Italian salumeria. Once fortified, walk the Freedom Trail to discover the rich history of the American Revolution and experience the modern city Boston is now.
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Guided Bike Tour of Boston

• 119 Reviews
• Discover Boston’s top attractions on this comprehensive 2.5- to 3-hour guided bike tour around the city. See the unique character and charm of each community up close, like the beautiful brownstones in Back Bay and the South End. Visit Boston’s historic North End, also known as Little Italy, and pedal past Copley Square, Fenway Park and Quincy Market. Ride along the Freedom Trail, a 2.5-mile path that passes by 16 locations significant to the history of the United States. It’s a classic tour and a great overall introduction to Boston.
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Boston Freedom Trail to Copley Square Walking Tour

• 51 Reviews
• Travel back in time through the early years of American history during this 2-hour guided walking tour of Boston’s famous Freedom Trail and its most iconic landmarks. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses and visit the setting of the infamous Boston Massacre. You’ll then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square. A professional guide will join your trip to help add context.
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Boston History & Highlights Small Group Walking Tour

• Explore Boston on foot with this small group walking tour. See highlights like Boston Harbor, Custom House Tower, Faneuil Hall, and Quincy Market. Learn the true story behind the Boston Massacre, and if you’re lucky, get a glimpse of government in action at the Massachusetts State House. See Beacon Hill, the Freedom Trail, and the lovely Boston Public Garden. Rest your legs and enjoy a beer with your local guide.
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Back Bay Wine Tasting and Walking Tour

• 17 Reviews
• Experience the best of Boston’s burgeoning wine scene on this 2-hour wine-tasting tour at some of the Bay Bay's finest restaurants. Learn about the historic area while sipping delicious wine varietals and enjoying tasteful food pairings. An expert guide will advise on what wine to select and what foods to pair each with. Tour numbers are limited to ensure an intimate experience.
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Downtown Freedom Trail Walking Tour in Boston

• 27 Reviews
• Spend 70 minutes exploring Boston's Freedom Trail on this informative and historic tour complete with a guide. You'll wander cobblestone streets, check out the architecture, and learn about the colorful past of this dynamic destination. Stops include Faneuil Hall, King's Chapel, Boston Common, and more.
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The Revolutionary Story Tour: An Epic Walking Tour of Boston

• 7 Reviews
• Make history engaging, and save yourselves the trouble of navigating through Boston. Learn the amazing history of the Revolutionary War in an experiential way through a small group 3-hour walking tour of Boston. See the major sights and hidden gems of the city in chronological order and experience the passion and drama of this era in history. Leave with a deep understanding of the twisting road to revolution and the mindset that built America.
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Copley Square to Downtown Boston Freedom Trail Walking Tour

• 5 Reviews
• Explore elegant neighborhoods, historic streets and American landmarks on a 2-hour Boston walking tour from the Back Bay to Beacon Hill and downtown portions of the Freedom Trail. Learn about Boston’s history and culture as you stroll brownstone-lined avenues and walk the shady paths of the Boston Public Garden. Step into Boston’s Revolutionary history in the churches, cemeteries and battlegrounds of the American struggle for independence.
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North End Wine Tasting and Walking Tour

• 1 Review
• If you’re not from the Boston area, it can be difficult to know where to go to taste some of the city’s best wine. This North End wine tour is led by a guide who takes you to the historic neighborhood’s elite local restaurants and well-curated wine shops for Italian wine pairings. Learn about the vintages and varietals of Italy in Boston’s Little Italy with a small-group limited to 12 for personalized attention the whole way.
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Boston Cultural All Day Tour with Local Guide

• Immerse yourself in the sights, food, and history of Boston on an all-day cultural tour. The comprehensive itinerary combines three themed tours to give you the ultimate Bostonian experience. Taste Italian pastries, visit the Old State House, and so much more. Transportation by water taxi and subway allows you to traverse the city like a local. Enjoy a game of bowling or billiards free of charge, before a final waterfront view.
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Small-Group Historical Walking Tour of Boston’s North End

• 16 Reviews
• Wander along the 18th-century streets and alleys of Boston’s historical North End neighborhood on this 3-hour walking tour. A historian-guide takes a small group, limited to just six people, in tracing the city’s evolution from the American Revolution to today. Stroll the same streets as Paul Revere and John Hancock, while hearing about the Boston Tea Party and the city’s shipping industry. It's a great to discover a side of Boston with an expert guide!
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Sweet & Savory South End Neighborhood Food Tour

• Sweet & Savory South End Tour Join us for a walking food tasting and cultural tour in Boston’s South End neighborhood. The rich history and renowned food scene found in the South End provide the perfect ingredients for a fun and memorable experience in one of Boston’s most vibrant and tasty neighborhoods!During this delicious experience, you can expect to: • Stroll the neighborhood streets and explore the South End • Sample food specialties from local eateries • Learn about the South End chefs and proprietors and how this neighborhood’s past has contributed to its modern culture
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PhotoWalks Freedom Trail Tour

• 39 Reviews
• Boston’s red-brick Freedom Trail takes you on a journey through revolutionary history, to sites where patriots protested against British rule and worked to form a new government. This walking tour takes you to famous sites along the trail, including Boston Common, the Old State House, and Park Street Church. While you walk, your guide provides historical background and offers tips for capturing photographs of these historic sites.
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PhotoWalks Beacon Hill Tour

• 11 Reviews
• Follow a friendly professional photographer guide through Beacon Hill and learn how to capture amazing pictures in less than two hours. Enjoy historical commentary as you navigate walkways between key landmarks and head home with incredible images that capture this leisurely adventure.
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South End Wine Tasting and Walking Tour

• The South End is one of Boston’s most vibrant neighborhoods, filled with Victorian brownstones, bustling restaurants, and a thriving bar scene. On this wine-centric walking tour you can experience some of the area’s best dining and drinking spots, dig into small plates, and learn how to taste, pair, and buy wine. The tour also offers a smooth dining experience, with a reserved table at each location and wait staff standing by to serve pre-selected wines.
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Private Customized Walking Tour of Boston

• 1 Review
• Explore Boston in a way that interests you on a private walking tour that can be customized to your preferences. You'll follow a flexible itinerary tailored to include attractions that you want to see, such as Boston Common, Freedom Trail, or Copley Square. If you don't have specific interests, you can leave the itinerary up to your guide. Either way, this is a chance to enjoy Boston's history and charm with a guide all to yourself.
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Tour de Boston Bike Tour

• Take a leisurely ride through Boston on the on this 2.5-hour cycling tour. Take in the Boston skyline, ride along the banks of the Charles River, and learn about Cambridge and Boston's history through your guide's commentary. Suitable for families with young children, this tour includes use of bike and helmet.
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Tour de Cambridge Bicycle Tour

• Experience the charms of Cambridge on this bicycle tour. Sometimes referred to as “Boston’s Left Bank,” Cambridge is a celebrated hub for academia, technology, and culture. Ride across the gleaming waters of the Charles River and visit Harvard Square, MIT, the Stata Center designed by Frank Gehry, and more. Over the course of 2.5 to 3 hours, you’ll cover 11-13 miles in this bike-friendly area.
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5-Day Boston Tour: Cape Cod with Nantucket and Whale Watch

• Experience Boston’s rich history, diverse neighborhoods, arts and culture, and the scenic Cape Cod peninsula on this multi-day tour. Your itinerary and accommodation is taken care of - all you have to do is show up. Start with a comprehensive city tour. Enjoy historic Nantucket Island. Watch humpback whales swim off the coast of Provincetown. Relax, knowing that you’ll sleep in comfort, eat delicious meals and appreciate all this maritime region has to offer.
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Fall Foliage Bike Ride in Boston

• Discover Boston’s fall beauty on this guided, 4-hour, small-group bike tour around the North End of the city. Explore the historic Emerald Necklace, a 1,100-acre chain of parks linked by parkways and waterways in Boston and Brookline. Visit the shaded boulevard on Commonwealth Avenue, the shores of Jamaica Pond, and the popular, winding paths of the Arnold Arboretum of Harvard University. Also, see the Rose Kennedy Greenway, Boston’s newest public park; the famous Charles River Esplanade; the Boston Common and Public Garden and much more.
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Boston Jewish Culture Walking Tour

• 2 Reviews
• Explore Boston’s Jewish heritage during this 2-hour walking tour of the city’s historic synagogues, Jewish monuments and key neighborhoods. Learn about the 19th-century Jewish roots of the Beacon Hill area and tour key Jewish gathering sites like the Vilna Shul. You’ll also get a look at Boston’s stirring Holocaust Memorial.
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Boston's North End and Waterfront Walking Tour

• 1 Review
• Explore the historic streets and landmarks of Boston’s oldest section on a 2-hour walking tour from downtown to the North End. Get a taste of Revolutionary New England as you visit key sites along the Freedom Trail, then immerse yourself in a colorful neighborhood with rich Italian American heritage. Follow in the footsteps of Paul Revere, the ‘Sons of Liberty’ and generations of immigrants with an experienced guide that brings their stories to life.
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Freedom Trail Private History Tour

• Explore Boston’s role in the American Revolution on a private walking tour of the Freedom Trail with former Boston National Historical Park ranger Ted Clark. Visit historic landmarks like Boston Common, King’s Chapel, and Massachusetts State House and learn what happened when this once-tiny colonial town found itself on the verge of war with the British. Enrich your visit to New England and experience revolutionary history with an informative guide.
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Little Italy Photography Tour

• 1 Review
• Explore Boston’s oldest neighborhood — North End, aka Little Italy — on a 90-minute walking tour with a professional photographer as your guide. Focus your camera lens on historic colonial landmarks such as the Paul Revere House and Old North Church. You’ll learn how to take better pictures and hear fascinating commentary along the way. Numbers are limited for a small-group experience.
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