Boston’s most worthwhile tours combine history, food, and local character into engaging experiences. The “Untold History Walking Tour” delivers fascinating stories beyond textbook facts, while the “Delicious Donut Adventure” connects visitors with beloved local bakeries and their mouthwatering specialties. For Revolutionary history buffs, the small-group “Freedom Trail Tour” offers an intimate look at America’s birth story without tourist crowds.
These reliable tours stand out for their knowledgeable guides, reasonable prices, and easy access from downtown hotels. They’re especially good for first-time visitors who want to understand Boston’s rich heritage while getting their bearings.
Let’s look at our favorite Boston tours worth your time and money.
Key Points
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The Freedom Trail Walking Tours offer 2.5-hour guided tours of 16 iconic sites, featuring knowledgeable French-speaking guides and engaging storytelling.
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The Boston Delicious Donut Adventure provides a 2-hour walking tour focused on exploring artisanal donut shops, with a high recommendation rate of 96%.
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The Culinary and Cultural Tours combine historical context, such as a visit to the Old North Church, with a 1.3-mile tour showcasing the city’s diverse culinary offerings.
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The Architectural Boat Tour offers a unique perspective on Boston’s diverse architectural styles, with knowledgeable guides providing historical insights.
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The Fenway Park Tour provides a 1-hour guided experience showcasing over 100 years of baseball history, with access to iconic landmarks like the Green Monster.
Boston City View Bicycle Tour by Urban AdvenTours
The Boston City View Bicycle Tour by Urban AdvenTours offers an immersive experience exploring the city’s diverse neighborhoods and iconic landmarks. Recommended by 97% of travelers, this 2.5-3 hour tour takes participants through 6 neighborhoods, including the North End, Back Bay, and Fenway Park.
Cyclists will visit top attractions like Fenway Park, Boston Common, and the Charles River Esplanade while pedaling along the Freedom Trail.
The tour starts and ends at Urban AdvenTours’ meeting point, with participants advised to arrive 30 minutes early for bike fitting and safety briefing. Groups are capped at 32 travelers, and an e-bike upgrade is available for those 16 and older.
Helmets are provided, and the tour operates in all weather conditions. Knowledgeable guides offer historical insights and local recommendations throughout the experience.
While the tour isn’t wheelchair accessible, it’s family-friendly and appropriate for ages 12 and up with a moderate fitness level. Non-refundable tickets can be rebooked for a $20 fee, and gratuities aren’t included in the price.
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Boston: The Untold History of Boston Walking Tour
Although the Freedom Trail is a popular highlight for visitors to Boston, this Boston: The Untold History of Boston Walking Tour takes travelers on a journey through the city’s lesser-known stories and hidden gems.
Priced at €24.00 per person, the 2.5-hour tour is conducted in English and is wheelchair accessible. It starts on Boylston Street and Tremont Street, where a guide with bright red hair will lead the small group.
During the tour, you will visit the Central Burying Ground, Boston Common, the Massachusetts State House, Old City Hall, Boston City Hall, Faneuil Hall, and the Boston Harborwalk.
Along the way, they’ll learn about the original Ponzi scheme, the bizarre Boston Molasses Flood, and the rise and fall of mobster Whitey Bulger.
The tour concludes at the Great Molasses Flood Plaque, offering a unique glimpse into Boston’s rich and often untold history.
Travelers can take advantage of the free cancellation policy and reserve their spot without upfront payment.
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Boston Delicious Donut Adventure by Underground Donut Tour
What better way to explore Boston than by indulging in its delectable donut scene? The Boston Delicious Donut Adventure by Underground Donut Tour offers a captivating experience, taking visitors on a walking tour of the city’s artisanal donut shops.
With 811 reviews and a 96% recommendation rate, this tour is a must-try for donut enthusiasts and those eager to explore Boston’s culinary heritage.
Priced at $70 per person and with a maximum group size of 20, the tour provides a personalized and immersive experience. Highlights include visiting hidden donut shops, sampling unique flavors, and exploring historical neighborhoods like the North End.
Travelers can also look forward to stopping at the Boston Public Market to browse local food vendors and indulge in apple cider donuts and fresh apple cider beverages.
The tour’s accessible and flexible nature, with a free cancellation policy up to 24 hours in advance, makes it a convenient and enjoyable way to discover Boston’s delicious donut culture.
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Nicky & Paulies Tour O Boston
Nicky & Paulies Tour O Boston offers a personalized and engaging exploration of Boston’s historic sites and hidden gems. Led by a father-son team, this 2-hour walking tour promises an authentic experience that goes beyond simply delivering facts.
With a focus on building relationships, the guides share unique insights into Boston’s history and haunted stories through captivating storytelling.
Priced at just $27 per person, the tour begins at Copps Hill Terrace, offering panoramic views of Boston Harbor and the Bunker Hill Monument.
Key stops include the Old North Church, Paul Revere Mall, North End, Christopher Columbus Waterfront Park, Faneuil Hall, Downtown Crossing, and the Granary Burying Ground, culminating at Boston Common.
Travelers can expect a relaxed and informative experience, with the added bonus of entry into the iconic Omni Parker House.
With an impressive 4.8/5 rating based on 6 reviews, Nicky & Paulies Tour O Boston is a must-consider for those seeking a personalized and memorable exploration of Boston’s rich history and culture.
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Boston: North End to Freedom Trail – Food & History Walking Tour
This 5-hour Boston tour takes visitors on an immersive journey through the North End and along the iconic Freedom Trail.
Operated by a B Corp certified company, the small-group experience offers personalized attention to no more than 12 people. Guests will explore the North End’s renowned Italian cuisine, enjoying three food stops with samples of fresh bread, pizza, meats, cheeses, pastries, and cappuccino.
They’ll also relax with a hot Italian beverage and pastry. The tour’s local food stops are 100% owned by community members, benefiting the neighborhood.
Along the Freedom Trail, knowledgeable guides share engaging stories and historical facts about the American Revolution, visiting sites like the Old North Church and locations of the Boston Tea Party.
Participants will discover Boston’s iconic landmarks, including the harbor and Beacon Hill.
Wheelchair accessible and child-friendly, the tour accommodates dietary requests and suits all ages and fitness levels, covering 5 miles of walking.
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Boston: Back Bay Small Group Walking History Tour
The Boston: Back Bay Small Group Walking History Tour invites visitors on a captivating 2.5-hour exploration of the city’s iconic Back Bay neighborhood. Priced at just $35 per person, the tour promises an intimate experience, with a maximum group size of 16 guests.
Led by knowledgeable historians, the tour delves into Boston’s pivotal role in the women’s suffrage movement from 1870 to 1920, uncovering the stories of local advocates who fought for voting rights.
Guests will stroll through the charming Back Bay, admiring the area’s Victorian-era architecture and landmarks, including the Boston Public Garden, Commonwealth Avenue Mall, Trinity Church, and Copley Square.
Along the way, they’ll learn about the historic figures and events that shaped the city’s rich heritage. The tour also includes entry into museums and landmarks, offering a deeper dive into Boston’s women’s history.
Whether you’re a history buff or simply seeking a unique urban adventure, this tour promises an engaging and enlightening experience.
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Boston History & Highlights Walking Tour
Although the charming Back Bay tour provides an enlightening glimpse into Boston’s women’s history, the Boston History & Highlights Walking Tour offers a comprehensive introduction to the city’s rich past.
Lasting 2 hours, this highly-rated tour explores Boston’s most iconic landmarks, including the Boston Harbor, the Custom House Tower, and the historic Beacon Hill neighborhood.
Led by knowledgeable local guides, the tour covers 4 km (2.5 miles) at a leisurely pace suitable for all ages and fitness levels.
Highlights include visiting the site of the Boston Massacre, the location of the first public school in America, and the Sons of Liberty and Boston Tea Party site.
Along the way, guests enjoy a surprise local treat.
With a maximum group size of 16, the tour provides personalized attention and ample opportunity to ask questions.
Conveniently located near public transportation, this tour is an excellent way to discover Boston’s storied past.
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Old Boston: Beacon Hill & Back Bay Walking Tour
Embarking on the Old Boston: Beacon Hill & Back Bay Walking Tour provides visitors an immersive glimpse into the city’s founding history and Gilded Age grandeur.
This 3-hour walking tour, led by a local French-speaking guide, explores the iconic Beacon Hill and Back Bay neighborhoods. During the tour, guests will discover the secrets of Beacon Hill, stroll through the Boston Public Garden, and admire the elegant Commonwealth Avenue and Newbury Street.
The tour concludes at the Prudential Center, offering panoramic views of the city’s skyline.
Priced at $45 per person, the tour accommodates a small group of up to 12 participants, ensuring an intimate and personalized experience.
Travelers can book the tour in advance and take advantage of the free cancellation policy.
With a wheelchair-accessible route and the inclusion of the Boston Public Library’s interior visit, this tour caters to a diverse audience seeking an authentic exploration of Boston’s past and present.
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Boston Small-Group Walking Food Tour With Tastings
Culinary enthusiasts visiting Boston can enjoy the city’s diverse food scene through the Boston Small-Group Walking Food Tour with Tastings. This highly-rated tour, boasting 94% traveler recommendation and a Badge of Excellence, offers a personalized experience capped at 12 participants.
For $115 per person, guests can sample iconic Boston delicacies, from clam chowder and lobster rolls to Italian brick oven pizza and tiramisu. The tour also features a secret dish revealed on the day of the excursion, ensuring an element of surprise.
Guided by knowledgeable locals, participants gain insider stories and historical insights as they explore notable stops like Union Oyster House, Modern Pastry, and Caffe Vittoria.
While the tour isn’t wheelchair accessible, most travelers can participate, as long as they’re prepared with comfortable walking shoes.
With generally positive reviews highlighting the engaging guides and delicious food, this tour provides an excellent opportunity for visitors to savor the flavors of Boston.
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Boston: Haunted Streets Walking Tour
Curious to uncover Boston’s dark and sinister past? Join the Boston: Haunted Streets Walking Tour and explore the city’s haunted history.
This 1.5-hour, 1.5-mile walking tour takes you through the heart of Boston, uncovering murder, mystery, and paranormal tales.
Led by a professional local guide in an orange hat or blue shirt, you’ll visit key sites like the Massachusetts State House, Boston Athenæum, and the ominous Omni Parker House, known as the most haunted hotel in America.
Hear chilling stories of the Hanging Tree of Boston Common and the second life of Crispus Attucks.
The tour includes photo stops and guided sightseeing at various historic locations, finishing at the Old State House.
Suitable for all visitors, this haunted walking tour promises spooky fun and an immersive exploration of Boston’s dark past.
Book now and pay later, with free cancellation up to 24 hours in advance.
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Boston Small-Group Freedom Trail History Tour Pub Crawl
Explore Boston’s rich history through the lens of its vibrant pub scene on the Boston Small-Group Freedom Trail History Tour Pub Crawl. Rated highly by 98% of travelers, this small-group tour combines visits to the city’s most significant historical sites with stops at top local pubs.
Led by knowledgeable Bostonian guides, you’ll learn about America’s formative years while enjoying the fun and engaging storytelling.
The tour offers two options – a Happy Hour Tour with pre-paid drinks, or a Dry Run where you can purchase drinks as you go. Both start at the iconic Sam Adams statue in Faneuil Hall and cover approximately 2 city blocks of walking, making it accessible for most.
Groups are capped at 12 travelers, ensuring an intimate experience.
Priced from $60 per person, this tour provides excellent value and the flexibility of free cancellation up to 24 hours in advance.
Whether you’re a history buff or just looking for a unique way to explore Boston’s pubs, the Boston Small-Group Freedom Trail History Tour Pub Crawl is a must-do.
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Boston: Holiday Sights and Festive Nights Trolley Tour
While the days grow shorter and the air grows crisper, Boston transforms into a winter wonderland. One way to experience the city’s festive charm is through the Boston: Holiday Sights and Festive Nights Trolley Tour. This 1-2 day hop-on, hop-off tour allows visitors to explore the city’s top attractions at their own pace.
Passengers can admire the twinkling lights and holiday decorations along the historic Freedom Trail, which brings to life the city’s role in the American Revolution. The tour also includes a stop at the iconic Faneuil Hall, where guests can browse the bustling marketplace and indulge in seasonal treats.
Plus, the trolley provides access to the picturesque Charles River Esplanade, offering stunning views of the city skyline.
With a duration of 1-2 days and a rating of 4.5 from 1,655 reviews, the Boston: Holiday Sights and Festive Nights Trolley Tour provides a convenient and enchanting way to experience the magic of Boston during the winter season.
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Bostons North End Pizza & History Walking Food Tour
The Boston’s North End Pizza & History Walking Food Tour offers visitors an engaging exploration of the city’s historic North End neighborhood and its renowned culinary delights. Spanning 2.5 hours, the tour takes guests on a journey through the cobblestone streets, uncovering the area’s rich Revolutionary-era history.
Highlights include the Paul Revere House, Old North Church, and the USS Constitution, all while learning about the influential figures who shaped Boston’s past.
The culinary experience is equally captivating, with three full-size pizza slices from popular local pizzerias and a classic cannoli from the renowned Modern Pastry.
Guides, known for their humor and historical insights, bring the neighborhood’s stories to life, providing an immersive and entertaining experience.
With an impressive 92% recommendation rate and a Badge of Excellence, this tour is a must-do for anyone seeking to discover the flavors and history of Boston’s iconic North End.
Whether you’re a history buff or a pizza enthusiast, this tour offers a delightful and well-rounded exploration of the city.
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Ghosts of Boston – Nighttime Walking Tour
What better way to experience the eerie and haunting side of Boston than on the Ghosts of Boston – Nighttime Walking Tour? This 1.5-hour small-group tour takes you through the city’s historic streets, revealing its spooky past.
Led by knowledgeable guides, you’ll visit sites associated with notorious ghosts and spirits, including the Omni Parker House, where the ghost of Harvey Parker is said to reside.
Along the way, you’ll hear chilling tales of Boston’s dark history and learn about the city’s most haunted locations. With a 4.5-star rating from 509 reviews, this tour is a must-do for those seeking a unique, spine-tingling experience.
Priced at €45.31 per person, it’s a thrilling way to explore the city at night. Whether you’re a history buff or simply love a good ghost story, the Ghosts of Boston – Nighttime Walking Tour is sure to leave you with goosebumps.
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Bostons North End Small Group Food Tour
Offering a delightful culinary journey through Boston’s historic North End, the Bostons North End Small Group Food Tour immerses visitors in the vibrant Italian-American culture of this iconic neighborhood.
With a 97% traveler recommendation and a Badge of Excellence, this tour promises an unforgettable experience, featuring three food stops where guests can sample meats, cheeses, pizza, pastries, and traditional Italian beverages.
Led by knowledgeable and friendly guides, the tour covers 1.3 miles, ensuring a personalized and engaging experience for a maximum of 12 participants.
Highlights include visiting the city’s oldest Italian salumeria, discovering a hidden Italian bakery, and enjoying a pizza at the guide’s favorite spot.
The tour also includes a visit to the Old North Church, providing historical context.
Wheelchair accessible and carbon neutral, this tour caters to various dietary needs, making it a must-do for anyone seeking an authentic taste of Boston’s North End.
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Boston: the Freedom Trail Is a Very Interesting Walking Tour in French
Immersing visitors in the rich history of Boston’s revolutionary past, the Freedom Trail Guided Walking Tour in French offers an engaging exploration of the city’s iconic landmarks. Priced from $45 per person, this 2.5-hour tour takes groups of up to 14 people through 16 emblematic sites, including the Massachusetts State House, Old South Meeting House, and the North End.
Led by knowledgeable French-speaking guides, the tour provides fascinating insights into Boston’s founding, the American Revolution, architecture, and cultural heritage.
Along the way, you will encounter modern sculptures like The Embrace and a Donkey, as well as discover the vibrant Italian scene in the North End.
With a 4.9/5 rating based on 49 reviews, the Freedom Trail Guided Walking Tour in French is widely praised for its engaging storytelling and local dining recommendations.
Whether you’re interested in history, architecture, or cultural experiences, this French-language tour is an excellent way to learn about the rich tapestry of Boston’s past and present.
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The Revolutionary Story Epic Small Group Walking Tour of Boston
Although Boston is renowned for its rich historical heritage, the Revolutionary Story Epic Small Group Walking Tour provides a captivating exploration of the city’s revolutionary past that goes beyond the typical Freedom Trail experience.
With a maximum group size of 16 travelers, this guided tour offers personalized attention and an immersive storytelling approach. Visitors will journey through 14 iconic landmarks, including Faneuil Hall and the Granary Burying Ground, while learning about the key events and characters that shaped the American Revolution.
The tour’s highlights include engaging guides, a built-in break at Quincy Market, and opportunities to capture memorable photos. Although not wheelchair accessible, the moderate walking pace makes it suitable for travelers in good physical condition.
At $76 per person, with free cancellation, this tour provides an exceptional value for those seeking an authentic and enriching experience in the heart of Boston.
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Cambridge, Massachusetts: MIT and Harvard Walking Tour
Where better to explore the cradle of American academia than on a Cambridge, Massachusetts: MIT and Harvard Walking Tour? This 3.5-hour excursion takes visitors through the storied campuses of two of the world’s most prestigious universities, providing an insider’s look at their rich histories, architectural gems, and legendary lore.
The tour begins at MIT, where a licensed guide shares fascinating facts about the institute’s pioneering innovations and notorious student pranks.
After a break, the group rides the subway to Harvard, strolling through the iconic Harvard Yard and admiring historic buildings that have housed generations of famous graduates.
The tour culminates at Kirkland House, offering a glimpse into undergraduate life.
At $49.99 to $42.49 per person, this tour delivers excellent value, with a subway ticket and gratuity included.
With a 4.7/5 overall rating based on 146 reviews, it’s clear this experience delights visitors seeking an engaging, informative exploration of Cambridge’s renowned academic institutions.
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Public Small Group Walking Tour of the Full Boston Freedom Trail
Tracing the iconic Freedom Trail, the Public Small Group Walking Tour offers an engaging exploration of Boston’s rich history.
Led by knowledgeable guides, the 2.5-hour tour takes visitors through all 16 official sites of the Freedom Trail, including the Bunker Hill, Paul Revere House, and historic burying grounds. Praised for their engaging storytelling and ability to bring the past to life, the guides share captivating tales about the American Revolution, abolition, women’s rights, and more.
The small group size of up to 25 travelers ensures a more personalized experience, allowing for ample opportunities to ask questions and interact with the guide.
Suitable for history enthusiasts and first-time visitors alike, the tour covers approximately 2 miles at a moderate pace, with breaks along the way. Conveniently accessible by public transportation, the tour is wheelchair and stroller friendly, making it an inclusive experience for all.
With a 97% traveler recommendation and a Badge of Excellence, this walking tour is an excellent way to take in the rich history of Boston.
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Boston: Harbor and Charles River Architecture Boat Tour
For those seeking a unique perspective on Boston’s architectural heritage, the Boston: Harbor and Charles River Architecture Boat Tour offers an immersive experience. Lasting 1.5 hours, this cruise allows visitors to admire the city’s diverse architectural styles from the water.
Guests will marvel at the blend of old and new, from the stately Federal-style buildings to the modern skyscrapers that dot the skyline.
With a rating of 4.4 out of 598 reviews, this tour provides an engaging and informative journey. Knowledgeable guides share insights into Boston’s rich history and point out notable structures along the way, such as the Customs House Tower and the John Hancock Tower.
Cruising along the Charles River also offers stunning views of the MIT and Harvard campuses.
Priced at $50.65 per person, the Boston: Harbor and Charles River Architecture Boat Tour is an excellent way to gain a unique perspective on the city’s architectural treasures.
This immersive experience isn’t to be missed for those interested in exploring Boston’s captivating blend of historical and modern design.
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Walking Tour Downtown Freedom Trail + Beacon Hill & Copley Square
The Walking Tour Downtown Freedom Trail + Beacon Hill & Copley Square offers visitors a comprehensive exploration of Boston’s rich history and architectural wonders. This highly-rated 2-hour walking tour takes participants through the city’s most iconic landmarks, including the Freedom Trail, Faneuil Hall, and the Boston Common.
Along the way, a professional guide provides engaging commentary, sharing historical anecdotes and insights into the city’s colonial past and modern-day evolution.
The tour covers a range of architectural styles, from the historic Old State House to the contemporary John Hancock Tower. Travelers will also witness the Victorian brownstones of Back Bay and the grandeur of the Boston Public Library and Trinity Church.
The experience culminates at the Copley Square, where participants can explore the city’s vibrant present. With a maximum group size of 20, the tour ensures an intimate and personalized experience.
Whether you’re a history buff or architecture enthusiast, this walking tour is an excellent way to discover the heart of Boston.
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Boston: Hop-On Hop-Off All Day Boston Sightseeing Tour
What better way to explore Boston’s iconic sights than with the Hop-On Hop-Off All Day Boston Sightseeing Tour? This tour offers the ultimate flexibility, allowing you to explore the city at your own pace.
With a duration of 1-2 days, you’ll have ample time to hop on and off the trolley as you discover Boston’s rich history and vibrant culture.
The tour covers 18 stops, including the Freedom Trail, Quincy Market, and the New England Aquarium. You’ll be able to admire the stunning architecture, learn about the city’s role in the American Revolution, and learn about the local atmosphere.
With a rating of 4.5 out of 5 from 1,655 reviews, this tour is a popular choice among visitors. At a price of around Kč 1,270 per person, it’s a great value for money, providing you with a comprehensive sightseeing experience in Boston.
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Tour of Historic Fenway Park, Americas Most Beloved Ballpark
Fenway Park, the iconic home of the Boston Red Sox, offers a one-of-a-kind tour experience for baseball enthusiasts, history buffs, and Boston aficionados alike.
This guided 1-hour tour takes visitors through over 100 years of legendary baseball history, providing access to iconic Fenway locations like the Green Monster and Pesky’s Pole. Knowledgeable guides share insights into Red Sox legends and relive the team’s storied World Series victories.
With a maximum group size of 180, the tour allows visitors to explore Fenway’s 170,000+ artifacts and 150,000 photographs in the living museum. Despite some complaints about large group sizes, the tour maintains an impressive 92% traveler recommendation based on over 2,300 reviews.
Whether you’re a die-hard Sox fan or simply curious about Boston’s rich baseball heritage, the Fenway Park tour is a must-do experience for any visit to the city.
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Ultimate US East Coast: Bundle of 25+Self-Guided Audio Tours
Explore the vibrant cities and stunning landscapes of the US East Coast with this comprehensive bundle of over 25 self-guided audio tours.
Discover Boston’s historical sites, from the iconic Freedom Trail to the picturesque harbor. Venture further north to explore the charming town of Salem, known for its rich history and witchcraft heritage.
Uncover the natural beauty of Martha’s Vineyard, a beloved island destination just off the Massachusetts coast. This flexible bundle allows you to create your own itinerary, with options to explore major cities like New York, Philadelphia, and Washington, D.C. at your own pace.
Each tour is narrated by engaging local guides, providing immersive insights and stories that bring the destinations to life.
Whether you’re a history buff, nature lover, or simply seeking to experience the diverse culture of the East Coast, this bundle is the perfect companion for a truly enriching and personalized journey.
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Freedom Trail: Small Group Tour of Revolutionary Boston
The Freedom Trail Small Group Walking History Tour provides an immersive exploration of Boston’s revolutionary past. With over 4,100 positive reviews and a 98% traveler recommendation, this 2.5-hour walking tour focuses on the American Revolution between 1760-1775. Guests will walk the Freedom Trail and see all 16 official historic landmarks, including Boston Common, Granary Burying Ground, and the Paul Revere House.
The tour’s small-group size (maximum 16 guests) creates an intimate atmosphere, allowing for personalized attention from the knowledgeable guides. Praised for their engagement and storytelling, the guides bring the city’s revolutionary history to life.
The tour is wheelchair and stroller accessible, making it inclusive for all travelers. Conveniently located near restaurants and shops, the tour offers flexible booking options, including free cancellation and a pay-later option.
At just $35.10 per person, the Freedom Trail Small Group Walking History Tour is an educational and enjoyable way to experience Boston’s rich revolutionary heritage.
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Sum Up
Boston offers a variety of engaging tours that cater to different interests. From biking through the city’s sights to exploring its rich history and delectable delights, there’s something for all. Whether you’re a first-time visitor or a local, these tours provide an excellent way to discover the charm and diversity of this vibrant city.