Highlights of Boston Private Tour - Starting the Day with Classic Italian Coffee and Cannoli at Caffe Vittoria

Highlights of Boston Private Tour

Discover Boston’s history, culture, and food on this private full-day tour featuring iconic sites, local markets, and expert storytelling for $390 per person.

Explore Boston’s Historic Neighborhoods and Iconic Sites in a Private Setting

Highlights of Boston Private Tour - Explore Boston’s Historic Neighborhoods and Iconic Sites in a Private Setting

The Highlights of Boston Private Tour offers an immersive experience through the city’s most celebrated neighborhoods and landmarks. Priced at $390 per person, this 5-hour 30-minute journey is ideal for those who want a rundown without the hassle of walking long distances. The tour includes private transportation, pickup from your location, and admission to key sites, making it a smooth and personalized way to explore Boston’s rich past and vibrant present.

This tour is highly recommended, with a 5.0 out of 5 rating based on 18 reviews, and 94% of participants suggesting it for others. It’s designed for travelers who appreciate history, culture, and good food, and is especially suited for those who prefer a comfortable, guided experience rather than self-guided wandering.

Key Points

Highlights of Boston Private Tour - Key Points

  • Private, full-day tour with a duration of 5 hours 30 minutes
  • Includes pickup from Boston hotels, airport, or cruise terminals
  • Visits historic sites like Old North Church, Paul Revere’s House, and Boston Common
  • Tastes local cuisine at the oldest restaurant in the US and the Boston Public Market
  • Guides provide engaging stories about Boston’s rebellion, corruption, and innovation
  • Flexible stops such as MIT, Kendall Square, and Copley Square enhance the experience

Starting the Day with Classic Italian Coffee and Cannoli at Caffe Vittoria

Highlights of Boston Private Tour - Starting the Day with Classic Italian Coffee and Cannoli at Caffe Vittoria

The tour begins with pickup at your preferred location in Boston, including hotels, the airport, or cruise terminals. You’ll then head to Caffe Vittoria to enjoy coffee, tea, and a cannoli, setting a warm and flavorful tone for the day. This 50-minute stop includes admission to the café, and is a perfect way to start with an authentic taste of Italy in Boston’s North End.

The cozy atmosphere of Caffe Vittoria, renowned for its Italian pastries, makes it an ideal first stop. It provides a chance to relax, fuel up, and prepare for a day full of exploration, with convenient pickup options for groups of up to six people.

Visiting the Historic North End and Paul Revere’s House

Highlights of Boston Private Tour - Visiting the Historic North End and Paul Revere’s House

Next, the tour takes you to North Square Park, home to Paul Revere’s House, one of the city’s oldest wooden homes. Amidst artwork and plaques, you learn about Boston’s immigrant history and the story of Revere’s midnight ride. This stop offers 20 minutes of free admission and gives insight into Boston’s revolutionary roots.

From there, the guide leads you to the Old North Church, where stories of rebellion and treason come alive while seated in a historic pew. This 25-minute stop highlights the pivotal moments that kicked off the American Revolution. With admission included, visitors gain a personal connection to Boston’s fight for independence.

Exploring Copp’s Hill Burying Ground and Revolutionary Landmarks

Highlights of Boston Private Tour - Exploring Copp’s Hill Burying Ground and Revolutionary Landmarks

The tour then moves to Copp’s Hill Burying Ground, Boston’s second-oldest cemetery. British troops occupied this site during the Revolution, and bullet holes in gravestones serve as a stark reminder of Boston’s turbulent past. This 15-minute stop is free to enter and offers a glimpse into Boston’s colonial and revolutionary history.

Following this, the Paul Revere Mall provides a scenic backdrop with the famous statue of Paul Revere and plaques of other Revolutionary figures. In just 10 minutes, visitors can appreciate this iconic location that captures Boston’s revolutionary spirit, while learning the truth behind the midnight ride.

Viewpoints on the USS Constitution and Bunker Hill

Highlights of Boston Private Tour - Viewpoints on the USS Constitution and Bunker Hill

From the Copp’s Hill Terrace, visitors get a wonderful view of the USS Constitution and Bunker Hill Monument across the water. During this 20-minute stop, the guide shares stories of the Siege of Boston and how George Washington and Henry Knox helped expel the British. It’s a perfect spot for photos and historical context without extensive walking.

Sampling Food and Shopping at Boston Public Market

Highlights of Boston Private Tour - Sampling Food and Shopping at Boston Public Market

A highlight for many is the one-hour stop at Boston Public Market, where the focus is on local, farm-to-table vendors. The market offers fresh chowder, bagels, sandwiches, smoothies, and more. Visitors also have the chance to browse souvenirs and experience Boston’s culinary scene firsthand. This stop appeals especially to those wanting a relaxed meal with options for every palate.

The admission is not included, but the market’s variety makes it easy to find something delicious. There’s also an option to enjoy a pint at America’s oldest continuously operated tavern or dine at the oldest restaurant in America nearby.

Strolling through Boston’s Parks and Government Buildings

Highlights of Boston Private Tour - Strolling through Boston’s Parks and Government Buildings

Next, the tour ventures through Boston Common, the oldest public park in America. Over 25 minutes, the guide shares stories of Boston’s founding while you enjoy the scenic green space. It’s an ideal spot for photos and to absorb the city’s historical atmosphere.

Immediately following, the Massachusetts State House presents a gold-domed symbol of state government. In 10 minutes, visitors see the historic building dating back over 200 years, learning about its significance and the stories it holds.

Walking Through Beacon Hill and Boston Public Garden

Highlights of Boston Private Tour - Walking Through Beacon Hill and Boston Public Garden

The walk continues into Beacon Hill, Boston’s most prestigious neighborhood. Over 20 minutes, the tour highlights the neighborhood’s wealthy families and historic architecture. The area is renowned for its gas lamps and charming streets.

From there, the tour visits the Boston Public Garden, the first botanical garden in the U.S. This 20-minute stop includes stories about Boston’s history and statues around the park, offering views of the Makepeace Fountain and the Swan Boats.

Innovation and Education in Kendall Square and MIT

The tour then drives to Kendall Square in Cambridge, known as “the most innovative square mile on the planet”. In 20 minutes, visitors see the headquarters of companies like Google, Apple, Moderna, and Pfizer. The area is famous for projects such as CRISPR and the Human Genome Project, emphasizing Boston’s role in cutting-edge science and tech.

Next, a drive-by of the MIT campus highlights the Great Dome, with stories about Famous pranks and the university’s “learning and doing” motto. This 20-minute stop offers a glimpse into Boston’s innovation hub without extensive walking.

Exploring Copley Square and Artistic Highlights

The final stop is Copley Square, a hub of culture and history. Over 15 minutes, the guide points out the Museum of Fine Arts, Northeastern University, and the John Hancock Tower. The Copley Library contains “America’s Sistine Chapel,” painted by John Singer Sargent over 30 years.

The tour concludes here, with drop-off available at a nearby hotel, airport, or cruise terminal for up to 6 people. The private transportation ensures comfort and convenience throughout the day.

Ease of Logistics and Included Perks

The tour vehicle is a Toyota Sienna minivan equipped with air conditioning. The pickup service covers hotels, airports, or cruise terminals in Boston, making arrival simple. Parking fees, fuel surcharge, and Old North Church entrance are included in the price, simplifying the experience.

Bottled water and a breakfast of coffee, tea, and cannoli are provided, along with parking fees, ensuring a comfortable start. Note that lunch is not included, allowing flexibility for personal preferences.

Who Will Appreciate This Tour Most?

This private tour is perfect for those seeking a rundown of Boston’s history, culture, and innovation in a relaxed setting. The inclusion of food stops, scenic views, and flexible scheduling makes it suitable for visitors who prefer personalized attention. It’s especially recommended for travelers who want a comfortable, informative day without the physical strain of walking extensively.

Final Thoughts on Value and Experience

While the $390 per person price reflects the private nature and wide range of sites visited, some reviews suggest that it offers good value for money, particularly for those interested in local stories, historic sites, and culinary delights. The knowledgeable guides and well-planned itinerary help maximize the experience, though some may find the lunch break slightly long or the price high for a shorter experience.

This Highlights of Boston Private Tour provides a balanced, engaging, and well-organized way to explore Boston’s most significant sights and stories in one day. It’s well-suited for those who want an informative, comfortable, and personalized introduction to the city.

✨ Book This Experience

Highlights of Boston Private Tour



5.0

(18 reviews)

89% 5-star

“We wanted a general tour of Boston without alot of walking as we are older with aches and pains! Ryan was a fantastic guide with a love of history….”

— Sallie B, Featured

Frequently Asked Questions

Is transportation included in the tour price?
Yes, private transportation via a Toyota Sienna minivan is included, along with pickup and drop-off services.

Can I customize the stops or itinerary?
The tour is private, so guides can tailor the experience based on your interests, with stops like MIT, Kendall Square, and historic sites.

Is lunch included?
No, lunch is not included, but there’s ample time at Boston Public Market to enjoy a meal from local vendors.

How long does the tour last?
The total duration is approximately 5 hours 30 minutes.

Are entrance fees included?
Yes, admission to sites like Old North Church and Paul Revere’s House are included in the price.

What should I bring?
Comfortable shoes are recommended for walking inside sites, but most walking is minimal. Luggage is limited to 4-5 suitcases in the vehicle.

Is this tour suitable for children?
Most travelers can participate, but small children or those unable to sit comfortably for the duration should consider their needs.

What makes this tour stand out?
The private setting, comprehensive itinerary, and engaging storytelling from guides like Ryan, Alex, and Maria provide an enriching Boston experience.

What is the cancellation policy?
Full refunds are available if canceled at least 24 hours before the scheduled start.

How do I book the tour?
Reservations are recommended in advance, with bookings typically made about 59 days ahead. For more details, contact Boston Hidden Gems at +1 617 297 8006 or via email at [email protected].