Private tours in Boston cut through the tourist crowds and deliver authentic experiences worth every penny. The Freedom Trail tours stand out, offering expert narration of Revolutionary sites like the Old North Church – you’ll learn stories most guidebooks miss. In the North End, food tours earn my highest recommendation, especially those stopping at family-run bakeries and traditional salumerias. For history buffs, the small-group walking tours of Beacon Hill and Back Bay give you the real stories behind Boston’s most elegant neighborhoods.
I’m particularly fond of the specialized tours focusing on specific themes – Revolutionary War history, Boston crime stories, or architectural heritage. These guides know their stuff and adapt the pace to match your interests.
Let’s look at the best private tours that showcase Boston’s rich heritage and local flavors.
Key Points
- Boston’s private historical tours, like the Freedom Trail and Unique Historical Perspectives, provide in-depth exploration of the city’s significant sites and lesser-known stories.
- Private culinary tours offer personalized experiences showcasing Boston’s diverse local specialties, from fresh seafood to North End delicacies.
- Family-friendly tours cater to families with children, emphasizing interactive learning and discovery of Boston’s rich history.
- Customizable private tours, such as smartphone photography and local insider experiences, provide a personalized and flexible sightseeing experience.
- For luxury travelers, Boston offers exclusive VIP tours, including helicopter rides and limousine services, along with tailored experiences like the Cape Cod and Provincetown day tour.
Boston: Food and History of The Freedom Trail Private Tour
The Boston: Food and History of The Freedom Trail Private Tour whisks visitors through the city’s rich culinary and historical tapestry.
Over approximately 5 hours, the tour explores Boston’s North End and Freedom Trail, visiting iconic sites. Guests sample local specialties like fresh bread, pastries, pizza, and meat & cheese snacks, completing a full meal.
The tour also includes admission to the Old North Church, a special Boston treat, and a drink from a local café.
Rated 4.9/5 based on 159 reviews, the tour is led by knowledgeable, engaging guides. Travelers praise the food quality and variety, though some suggest including more Boston-specific dishes.
Read our full review: Boston: Food and History of The Freedom Trail Private Tour Review
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Boston Food of the North End Private Walking Tour
Visitors can embark on a captivating 2-hour Boston Food of the North End Private Walking Tour, which offers a delectable exploration of the city’s vibrant culinary scene.
Priced from $147 per person, this private group tour allows guests to discover the iconic Quincy Market, the historic North End, and other notable landmarks, including the Old North Church and the Paul Revere Mall.
The experience features a range of tastings, including freshly baked bread, zesty pizza, pastries, and more, amounting to a full meal.
Led by a local English-speaking expert, the tour offers the opportunity to make reservations at popular spots, ensuring an unforgettable culinary adventure.
Read our full review: Boston Food of the North End Private Walking Tour Review
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Heart of the Freedom Trail in Boston: 60 Min Private Tour
This 1-hour private walking tour along Boston’s iconic Freedom Trail offers a captivating glimpse into the city’s pivotal role in the American Revolution.
Led by a highly trained local guide, the tour covers key historic sites like the Old State House, Faneuil Hall, King’s Chapel, and Old South Meeting House.
For $175 per group of up to 12 participants, guests can explore the stories of ordinary people who achieved extraordinary things during this transformative period.
The tour is wheelchair accessible, and guests can reserve their spot without an upfront payment, with free cancellation up to 24 hours in advance.
Read our full review: Heart of the Freedom Trail in Boston: 60 Min Private Tour Review
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Boston Seafood Private Tasting Tour
A captivating Boston Seafood Private Tasting Tour takes guests on a delectable journey through the city’s renowned Seaport District and waterfront.
Boasting over 100 reviews with a 97% traveler recommendation, this tour delivers a Badge of Excellence experience. Visitors can savor locally-sourced seafood delights like lobster rolls, New England clam chowder, and fried oysters.
The tour includes a full-meal lunch, a knowledgeable local guide, and gratuities. Although it’s wheelchair and stroller accessible, the tour is shellfish-focused with no accommodations for dietary restrictions.
Priced from $173 per person, the tour offers free cancellation and a lowest price guarantee, making it a compelling option for those seeking an authentic Boston seafood experience.
Read our full review: Boston Seafood Private Tasting Tour Review
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Boston by Little Feet Walking Tour: 60 Min Private Tour
Boston’s “Boston by Little Feet Walking Tour: 60 Min Private Tour” offers families a captivating exploration of the city’s revolutionary history.
This 60-minute private tour, designed for children aged 6-12, promises an interactive and engaging experience. Led by passionate local guides, the tour takes participants along the Freedom Trail, highlighting key sites like Faneuil Hall, the Old State House, and the Old South Meeting House.
Families can discover the first public school in America and explore Boston’s oldest burying ground. With a focus on encouraging discovery and exploration, the tour provides a unique opportunity for children to enjoy the city’s rich past.
Priced at $175 for up to 12 participants, this tour ensures a personalized and memorable experience.
Read our full review: Boston by Little Feet Walking Tour: 60 Min Private Tour Review
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Boston History and Freedom Trail Private Walking Tour
Enjoy Boston’s storied past on the Boston History and Freedom Trail Private Walking Tour.
This highly-rated 2-hour experience takes you through downtown Boston and the Seaport District, visiting iconic sites like the Boston Massacre, Boston Tea Party, and Paul Revere’s home.
Led by knowledgeable local guides, the small-group format ensures a personalized and engaging encounter.
Explore the city’s rich history, hidden gems, and vibrant art and food scene at a comfortable pace.
With a 4.9-star rating, 96% traveler recommendation, and a Badge of Excellence, this private tour delivers an exceptional experience, from start to finish.
Priced at $245 for up to 12 guests, it’s a must for history buffs and first-time visitors alike.
Read our full review: Boston History and Freedom Trail Private Walking Tour Review
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The Dark Side of Boston: 90 Min Private Walking Tour
While the Boston History and Freedom Trail tour takes visitors through the city’s storied past, the Dark Side of Boston: 90 Min Private Walking Tour delves into the lesser-known chapters of the city’s history.
Led by highly trained local guides, this 1.5-hour private walking tour focuses on true historical events related to misery, misfortune, and murder in Boston.
Participants will explore the winding streets and alleyways of the North End, learning about the Great Influenza of 1918, smallpox outbreaks, the Molasses Flood, and the Brinks Robbery.
With flexible booking and free cancellation, this tour offers an engaging and unique perspective on Boston’s checkered past.
Read our full review: The Dark Side of Boston: 90 Min Private Walking Tour Review
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VIP Private Tour
Travelers seeking an exclusive airborne encounter over Boston can indulge in the VIP Private Tour. Priced at $599 per person, this 30-minute private helicopter excursion offers panoramic views of the city’s iconic skyline.
The experience includes stylish hotel pickup, refreshments in a lounge before the flight, and a personal pilot for a seamless journey. After the tour, guests can unwind in a VIP lounge with premium snacks and beverages.
The package also features a Champagne offering with champagne and Swiss chocolate truffles. While not suitable for wheelchair users, the tour provides an optional black car service for downtown hotel transfers and post-tour return.
Read our full review: VIP Private Tour Review
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Boston: Luxor Limo Private Transfer and City Tour
For those seeking a luxurious and personalized way to explore Boston, the Luxor Limo Private Transfer and City Tour offers an unparalleled experience.
Starting at $1,195 for up to 14 people, this service includes airport transfers, corporate transportation, and customized packages. Clients can choose from a fleet of sedans, SUVs, stretch limousines, and party buses, all designed for comfort and style.
Highly trained, multilingual chauffeurs ensure safe and enjoyable rides, with amenities like bottled water, WiFi, and music systems. Pickup and drop-off are included, though the service isn’t suitable for those with mobility issues or young children.
Read our full review: Boston: Luxor Limo Private Transfer and City Tour Review
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Best of Boston: Full-Day Private Tour
The full-day “Best of Boston: Full-Day Private Tour” offers an immersive experience, allowing visitors to uncover the city’s rich history and vibrant culture.
Priced at Kč 14,244 for up to 2 participants, the 5.5-hour tour includes van transportation, a breakfast stop, guided walks, and free time to explore landmarks like the Freedom Trail and Boston Public Market.
Guests can expect a personalized experience with knowledgeable guides, as well as opportunities to learn about the city’s immigrant stories, colonial history, and architectural gems.
With convenient pickup and drop-off options, this tour provides a comprehensive and flexible way to discover the best of Boston.
Read our full review: Best of Boston: Full-Day Private Tour Review
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Boston: Private Walking Photography Tour
Boston’s Private Walking Photography Tour offers a unique opportunity to capture the city’s iconic sights while developing one’s photography skills.
Priced at Kč 3,112 per group (up to 2 participants), the 1-hour tour is led by a live guide who provides tips and tricks for improving smartphone photography.
Participants will visit top attractions, receive 20-30 professionally edited digital images, and send a postcard with their favorite tour photo.
The tour is wheelchair accessible, and free cancellation is available up to 24 hours in advance.
With an overall rating of 4.3/5 based on 6 reviews, the tour is suitable for various traveler types, including couples, friends, solo travelers, and families.
Read our full review: Boston: Private Walking Photography Tour Review
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Welcome to Boston: Private Tour With a Local
Travelers seeking an immersive Boston experience can embark on a private tour with a local guide. Priced from Kč 1,317 per person, the 2-6 hour tour offers a personalized exploration of the city from a local’s perspective.
Guests can discover insider tips on grocery shopping, dining, and navigating Boston’s streets. The tour is fully customizable based on personal interests, with the option to meet at a hotel or central landmark.
With a 4.5/5 overall rating and positive feedback highlighting friendly, knowledgeable guides, this private tour provides an authentic and insightful way to experience the city.
Free cancellation up to 24 hours in advance allows for flexibility in planning.
Read our full review: Welcome to Boston: Private Tour With a Local Review
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Boston: TV and Movie Filming Sites Private Tour
For movie buffs and TV enthusiasts, a private tour of Boston’s celebrated filming locations offers an immersive journey into the city’s cinematic history.
This 2.5-hour guided walk showcases iconic sites featured in popular movies and TV shows, from the Irish mob drama The Departed to the crime thriller Blown Away.
Guests will explore the picturesque streets and landmarks that have graced the silver screen, gaining insider knowledge and behind-the-scenes stories from their knowledgeable guide.
Whether you’re a film fanatic or simply curious, this private tour provides a unique opportunity to experience Boston through the lens of Hollywood.
Read our full review: Boston: TV and Movie Filming Sites Private Tour Review
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From Boston: Cape Cod and Provincetown Private Day Tour
From Boston’s bustling city center, a private day tour whisks visitors away to the picturesque Cape Cod and the charming seaside town of Provincetown.
The tour, priced at Kč 27,172 for up to 6 participants, offers a 9-hour customizable experience with guided explorations of the Cape Cod National Seashore, Race Point Beach, and other iconic landmarks.
Travelers can enjoy a 1.5-hour ferry ride, interact with local life, and opt for activities like sand dune tours and whale-watching.
With a live English-speaking guide, the tour promises panoramic views, architectural discoveries, and the opportunity to savor the region’s unique culinary offerings.
Read our full review: From Boston: Cape Cod and Provincetown Private Day Tour Review
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Boston Freedom Trail to Harvard Square Private Driving Tour
Setting out on a private driving tour, visitors can explore Boston’s iconic Freedom Trail and prestigious Harvard Square.
This 6-hour excursion covers significant sites along the Freedom Trail, including Faneuil Hall, Paul Revere House, and Boston Common.
The tour also ventures into neighborhoods like the North End, Back Bay, and Charlestown, showcasing landmarks such as the Massachusetts State House, Old State House, and Granary Burying Ground.
Optionally, guests can visit Fenway Park, Old North Church, Harvard University, and the John Harvard Statue.
Throughout the experience, the knowledgeable guide provides insights into Boston’s pivotal role in American history and its cultural significance, from the Boston Massacre to the city’s architectural and culinary offerings.
Read our full review: Boston Freedom Trail to Harvard Square Private Driving Tour Review
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Boston Citywalks: Private Personalized Walking Tour
Visitors seeking a personalized introduction to Boston can embark on the Boston Citywalks: Private Personalized Walking Tour.
This 2.5-hour walking tour offers a customized experience, tailored to the interests and pace of each group. Guests can explore the city’s iconic landmarks, historic neighborhoods, and hidden gems with a knowledgeable local guide.
The tour covers popular sites like the Freedom Trail, Quincy Market, and Newbury Street, while also delving into the city’s rich history and contemporary culture.
With flexible start times and the ability to adjust the itinerary, this private walking tour provides a unique and authentic way to discover the best of Boston.
Read our full review: Boston Citywalks: Private Personalized Walking Tour Review
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Boston: Private Driving Tour With a Local Guide
Exploring Boston’s iconic landmarks and historic neighborhoods has never been easier than with the Boston: Private Driving Tour With a Local Guide.
This 3-hour private driving tour covers the Freedom Trail‘s 16 significant Revolutionary War sites, including the Old South Meeting House, Old State House, and Bunker Hill Monument. Guests also explore neighborhoods like Beacon Hill, Back Bay, and the North End, while taking in scenic views of Boston’s architecture and green spaces.
Led by a fully licensed guide, the tour offers insights into the city’s rich history and culture, with the convenience of a luxury van and the flexibility to access areas not accessible by larger vehicles.
With free cancellation and a pay-later option, this tour is an excellent way to experience Boston.
Read our full review: Boston: Private Driving Tour With a Local Guide Review
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From Boston: Private Lexington and Concord Driving Tour
Immersing oneself in the historic sites of Lexington and Concord is a captivating experience offered by the private driving tour from Boston. Priced at $640 per group, the 5-hour excursion provides a personalized exploration of the region’s significant landmarks.
Visitors can discover the Lexington Battle Green, the Minute Man statue, and the Old North Bridge where the “shot heard round the world” was fired. The tour also includes a visit to Walden Pond and Louisa May Alcott’s Orchard House.
Along the way, the knowledgeable guide offers optional tours at various sites, ensuring an educational and engaging journey through this historic area.
With flexibility, convenience, and excellent customer reviews, this private tour is an ideal way to explore the rich history of Lexington and Concord.
Read our full review: From Boston: Private Lexington and Concord Driving Tour Review
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The Sum Up
Boston offers a variety of private tours that allow visitors to explore the city’s rich food, history, and culture. From walking tours of the Freedom Trail and North End to driving tours of Lexington and Concord, there’s something for all. These tours provide an intimate and personalized experience, giving travelers a deeper understanding of Boston’s past and present.