Boston
Sightseeing Walking Tours

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Our most recommended Boston Sightseeing Walking Tours

Boston Fenway Park: 1-Hour Guided Walking Tour

1. Boston Fenway Park: 1-Hour Guided Walking Tour

Explore the historic grounds of Fenway Park, a true Boston icon since 1906. Visit the home of the Boston Red Sox. Become enchanted by the charm of this 109-year-old Boston monument. Be led by a guide on a 1-hour walking tour of Fenway Park. This authentic gem is home to celebrated baseball World Champions from 1903, 1912, 1915, 1916, 1918, 2004, 2007, 2013, and 2018. On the public guided tour, view the stadium and baseball field where Red Sox legends Williams, Yaz, Fisk, and Rice made their mark on Red Sox Nation. See Pesky's Pole and sit atop the world-famous Green Monster, which stands 37 feet 2 inches high overlooking left field. Take in the magnificent sights and breathtaking views of Boston atop the Roof Deck overlooking right field. Finish your tour at the Fenway Park Living Museum collection, which engages fans of all ages by showcasing the vast collection of Red Sox baseball memorabilia. Fenway Park is not only a local favorite but also an international tourist destination visited by fans from over 93 different countries. Upgrade your experience to a private tour that takes you through the same places as the public tour, but also gives you the opportunity to visit exclusive locations (subject to availability). Your guide will let you know what is available that day once you check-in for the tour. With the upgrade, you can cover the Red Seat, Visiting Team Clubhouse, Visiting Team Batting Cage, Red Sox Hall of Fame, Red Sox Front Office and Trophy Case, Batting Titles & Golden Glove Awards Display, State Street Pavilion Club, Warning Track, and Green Monster Scoreboard. 

Harvard: 70-Minute Harvard Tour

2. Harvard: 70-Minute Harvard Tour

What better way to see Harvard than through the eyes of a student! This tour is a 70-minute student-led walking tour of America's oldest university, designed to be a funny and educational journey through Harvard's campus. Beginning in the heart of Harvard Square, you'll be led into historic Harvard Yard by an enthusiastic Harvard student. Enjoy the sights while your guide entertains and inspires with tales of Harvard history and personal experience at the university they call home. You'll get an up-close look at major Harvard landmarks including Johnston Gate, the John Harvard Statue, Memorial Hall, and Widener Library. You'll even become privy to a few Harvard secrets along the way! Whether you're a student visiting colleges or a family on vacation, the Hahvahd Tour is undoubtedly the top way to see Harvard.

Boston: 2.5-Hour Walking Tour of the Freedom Trail

3. Boston: 2.5-Hour Walking Tour of the Freedom Trail

See all 16 of Boston's Iconic Freedom Trail sites in a single 2.5-hour tour with an experienced guide. Learn about icons like Paul Revere and John Hancock, along with lesser-known stories of women, African Americans, and immigrant patriots and pioneers. Discover tales of rebels, gangs, and Midnight Riders, with a few cheap dad jokes for good measure. Gain an understanding of Boston's role in the American Revolution and how the city became a pioneer in the fields of abolition, American education, and immigration. Start your tour opposite the Massachusetts State House and finish in the North End with the best view of the Charlestown Freedom Trail sites. Along the way, experience the explosive events of the American Revolution like the Boston Tea Party and the Boston Massacre in the places they happened.

Boston: Historic Walking Tour of the Freedom Trail

4. Boston: Historic Walking Tour of the Freedom Trail

Learn about the tumultuous 15-year period that culminated in the American Revolution on this small-group walking tour. As you walk through Boston, you’ll follow the footsteps of colonial Bostonians, all of whom grappled with the difficult question of loyalty or rebellion to crown and country. Start your walking tour on Boston Common, where the Freedom Trail originates. From there, you'll begin your walk along the historic Freedom Trail with your guide. Along the way, learn the significance of landmarks such as the Granary Burying Ground, the Old South Meeting House, the Boston Massacre Site, the Old State House, Faneuil Hall, and more. Your walking tour concludes at either Faneuil Hall (1.5-hour option) or Copp's Hill Terrace (2.5-hour option). The 1.5-hour tour visits 11 of 16 official Freedom Trail landmarks and the 2.5-hour tour includes views of all 16 official landmarks.

Boston: History After Dark Haunted Walking Tour

5. Boston: History After Dark Haunted Walking Tour

Embark on a unique after-dark tour and explore downtown Boston’s most haunted hotspots. Discover both the paranormal and historical worlds of each carefully selected tour site and listen to researched, authentic, and up-to-date accounts that ensure you have the best, most chilling experience possible. Highlights of the tour include: Omni Parker House Haunted by its first owner and other notable ghostly guests, the Omni Parker House is considered Boston’s most haunted location. One room, in particular, has caused so much trouble, terror, and grief that the hotel was eventually forced to convert it into a storage room, lest they risk another guest suffering from a grisly night’s stay in the cursed room. What could possibly drive a hotel to permanently retire an otherwise perfectly good guest room? Discover the details on our tour. Boston Common This seemingly placid area is the country’s oldest park. For a century of its long history, Boston Common was the site of hundreds of hangings. Not all of the victims of these executions managed to escape the park, even after death. The grim ghosts of the hanging victims are the least of your paranormal concerns in the Common. Keep your eyes open and your wits about you whenever you’re at this park… or else. Old South Meeting House Witness the birthplace of the Boston Tea Party protest and the very American Revolution itself at the Old South Meeting House. This building is of crucially historic importance, but that’s not the only legacy the meeting house is known for. It is a specter that sometimes appears and always acts as a harbinger of impending death. Or perhaps it’s no messenger of death at all, but instead directly responsible for the string of deaths that have befallen the unlucky ones who’ve encountered it. Old City Hall This former hub of Boston’s local government has since become a bustling mixed-use commercial and office property. Because of its historical significance being covered up with the new polish of redevelopment, at least one ghost exacts its revenge for this perceived disrespect for history on visitors. The Old City Hall may be magnificent looking, but watch where you look inside…

Historic Pub Crawl Tour along the Freedom Trail

6. Historic Pub Crawl Tour along the Freedom Trail

Wander along the same cobblestone streets as Paul Revere once did, pass through bustling markets where Sam Adams peddled the idea of revolution. Visit historic bars that have been frequented by Bostonians for hundreds of years. Revisit the story of America's birth and raise a glass as you learn the importance of beer in the founding of America. This historic pub crawl reveals hidden history about the events leading up to the revolutionary war and takes you where it all started: taverns. The four historic taverns visited on the tour are in the Faneuil Hall area and provide a wonderful backdrop as expert guides tell stories about Boston's rebellious past that helped lead to America's independence. Each tavern dates back at least to the 1800's, several even further which includes America's oldest tavern! At each tavern your guide will recommend beer as unique as the history of the city. Most of the beers are exclusively served in Boston and several can only be found in the taverns visited on the tour!

Boston: Freedom Trail Tour

7. Boston: Freedom Trail Tour

Start the tour from the official Visitor's Center on America's first public park, The Boston Common. Meet your colonial-costumed historical interpreter and guide before embarking on a journey through Boston's colonial history. Spot lots of incredible historical sites along this short 1.2-mile stretch between The Boston Common and Faneuil Hall. Pass by the Granary Burial ground where American Fore Fathers are buried, and the site of the world-famous Boston Massacre. Also discover the Park Street Church, America's first public school, the site of The Boston Tea Party, the Old State House, and the Old South Meeting House. Finally contemplate Boston's most visited attraction, Faneuil Hall.

Boston: 2.5-Hour City View Bike Tour

8. Boston: 2.5-Hour City View Bike Tour

The Urban AdvenTours Boston City View Bicycle Tour offers a classic ride for those looking to get a great overall introduction to the city. During the 2.5-hour tour you’ll get to know the city and find neighborhoods that you can explore in greater depth later. Discover the unique character and charm of each area you visit up close, in person, and only possible by bicycle. This comprehensive tour covers all of Boston’s best sites, including: • Historic Fenway Park • The Christian Science Center • Boston Common • The beautiful brownstones in Back Bay and the South End • The Rose Kennedy Greenway, Boston’s newest public park • The Charles River Esplanade • The North End, Boston’s oldest residential, Italian neighborhood • Copley Square, where you’ll see the Boston Public Library, Trinity Church, and the John Hancock building The City View tour includes an individually-fitted bike, helmet, water, and of course, a friendly and knowledgeable guide who will lead you on your travels. The tour covers 10-12 miles, from the bustling streets of downtown, to the serene bike paths along the Charles River, this tour truly brings you the best of Boston by bicycle! You can opt to do the City View tour on a regular hybrid bike, or on a pedal assist electric (e-bike). Select your bike choice at the time of booking.

Boston: Fall Foliage Tour

9. Boston: Fall Foliage Tour

Your day will start with pickup from your hotel in greater Boston. From here, you will make the 2-hour ride north into New Hampshire surrounded by the beautiful fall colors as you drive higher into the mountains. You'll make a short stop half-way along for coffee or cider. Once on the Kancamagus Byway, you will make several stops for pictures of the mountains and fall foliage colors. Your knowledgable guide will share details about the region. You'll also enjoy 2 short excursions on easy to hike trails to view historic waterfalls. Then, enjoy a 1.5-hour lunch and shopping break in the mountain town of North Conway. This is a quaint town surrounded by snow-capped mountains and rugged cliffs. After lunch, you'll head further into the White Mountains. The last stop will be near the spectacular Omni Mount Washington Hotel. Many have called this "the highlight of the tour" as this beautiful location neighbors New Hampshire's tallest and most extravagant mountain range. Finally, your guide will point out a few more interesting sights before the 2-hour journey back to your hotel in Boston.

Boston: Italian Food Tour with Pizza, Meats, Cheese, & Bread

10. Boston: Italian Food Tour with Pizza, Meats, Cheese, & Bread

Your North End experience begins at the lifeblood of Boston, the Boston Harbor. Walk through a scenic waterfront park, with views of the harbor, East Boston and the historic wharfs lining Atlantic Ave. Make your way to the heart of the North End, with views of some of the most historic sites and properties in the neighborhood, some dating back to the late 1600s and early 1700s. Delicious food is never far away in the North End. Your guide will introduce you to a small, hidden Italian bakery serving up fresh bread daily. Break bread with your fellow travelers and let the carbs give you the energy to continue your adventure! A proper Italian salumeria is next, and you’ll have a chance to enjoy Italian meats and cheeses at their finest and freshest.  Next up, take in the energy of the North End’s busiest corridor, Hanover Street. It’s time for a mid-tour break with your guide at a traditional Italian café. Here, you will have a chance to enjoy your choice of a classic cappuccino, espresso, or tea. Let the caffeine kick in as you go back in time into North End history. You’ll hear stories about some of the most influential events that have happened in Boston, including Paul Revere’s midnight ride. Make your way to the Old North Church and step inside the hallowed walls. To this day, North Enders still attend this church, which is famous for its role in the Revolution.  After church, dive deeper into the local side of the North End. A taste of pizza awaits at a neighborhood favorite and the stories are endless. Cap off the North End food experience with samples of the best of the best Italian pastries along the backstreets of this delicious neighborhood. Hopefully, there will be a chance to meet and chat with the area’s top bakers if you catch them at a quiet moment.  After the tour, you’ll surely be ready to make a dinner reservation. Consult with your guide for the best recommendations and you will be set up for an amazing time in Boston.

Frequently asked questions about Boston Sightseeing Walking Tours

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Other Sightseeing Options in Boston

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What people are saying about Boston

Overall rating

4.7 / 5

based on 1,852 reviews

I had a wonderful time with Deniss! She was warm, energetic and took the initiative to ask me about the areas I wanted to explore beforehand. She showed me around some of the more unique landmarks in seaport and brought me to a lovely tea house! She even shared pieces of Boston’s history and some travel tips with me which was a huge bonus! At the end of the tour, she was even kind enough to show me the way back to my student accommodation as it was my first time taking the T. A great experience!

Daniel our tour guide was fabulous. He was polite, knowledgeable, and kept us engaged and entertained at the same time. He provided fantastic history of Boston and his stories were informative. Highly recommend this tour when visiting Boston and hopefully you can get Daniel.

Our tour guide, Mark, was very knowledgeable, informative, encouraging, and entertaining. He brought an engaging perspective to the varied sites we visited! A great tour for those who enjoy history!

A great tour. Highly recommended for all sports, stadium and history fans.

Great tour! Informative and fun. Our guide, Caitlin, was excellent