4 Private Tours and Day Trips from Boston: Boston, Lexington & Concord, Plymouth and Newport

Boston is one of the best starting points for exploring New England history, architecture and coastal destinations. Within the city and a comfortable drive from Boston, travelers can experience Revolutionary War landmarks, early colonial history, historic mansions, waterfront communities and some of the most recognizable sites in Massachusetts and Rhode Island.

Boston Preferred Car Service offers four distinct private sightseeing experiences for travelers staying in Boston: a Private Boston City Tour, a Private Boston, Lexington & Concord Historical Tour, a Private Plymouth Day Trip and a Private Newport Day Trip.

Although all four experiences include private transportation reserved for your party, they are not exactly the same type of service. The Boston City Tour and Boston, Lexington & Concord experience are guided historical tours with narration, while Plymouth and Newport are primarily private chauffeured day trips where passengers explore major attractions independently while the chauffeur remains available with the vehicle.

This guide explains the differences between the four experiences, what travelers can expect to see and which private tour or day trip may be the best fit for a visit to Boston.

Four Private Tours and Day Trips from Boston

Itineraries and timing are flexible and may vary according to traffic, attraction operating hours, ticket availability, weather, the interests of the passengers and the amount of time spent at individual locations.

1. Private Boston City Tour

For visitors who want to understand Boston’s history and major neighborhoods without devoting an entire day to sightseeing, the Private Boston City Tour provides a guided introduction to the city.

The standard experience is approximately 4 hours and combines historical narration with private transportation between important landmarks. Because the tour is private, the itinerary can be adjusted according to the interests and pace of the passengers.

What Can You See on a Private Boston City Tour?

The itinerary may include selected landmarks along Boston’s Freedom Trail as well as some of the city’s most recognizable neighborhoods and sightseeing areas.

Depending on traffic, available time and the interests of the party, highlights may include:

• Boston Common
• Massachusetts State House
• Granary Burying Ground
• Old State House
• Boston Massacre Site
• Faneuil Hall
• Paul Revere House
• Old North Church
• Beacon Hill
• Back Bay and Copley Square
• Fenway Park
• USS Constitution
• Bunker Hill Monument
• Harvard and Cambridge

The tour does not need to follow one rigid sequence. Travelers interested primarily in Revolutionary history may choose to spend more time around the Freedom Trail, while other visitors may want a broader introduction to Boston’s neighborhoods, architecture, universities and waterfront areas.

Who Is the Boston Private City Tour Best For?

The Boston City Tour is particularly well suited to:

• First-time visitors to Boston
• Travelers with only one free morning or afternoon
• Couples, families and small private groups
• Business travelers with limited sightseeing time
• Visitors who prefer to see more of Boston without walking the entire Freedom Trail

Learn more: Private Boston City Tour

2. Private Boston, Lexington & Concord Historical Tour

For travelers who want to go deeper into the story of the American Revolution, the Private Boston, Lexington & Concord Historical Tour follows the Revolutionary story from Boston to the communities where armed conflict began on April 19, 1775.

The standard experience is approximately 6 hours and includes historical narration and private chauffeured transportation throughout the journey.

Rather than treating Boston, Lexington and Concord as three unrelated sightseeing destinations, the tour connects the political events in Boston with the military expedition that eventually led to the confrontations at Lexington Battle Green and Concord’s North Bridge.

Revolutionary Boston and the Freedom Trail

The experience begins in Boston with selected sites associated with the events and personalities that helped move Massachusetts toward revolution.

The Boston portion may include landmarks such as:

• Boston Common
• Massachusetts State House
• Granary Burying Ground
• Old State House
• Boston Massacre Site
• Faneuil Hall
• Paul Revere House
• Old North Church

The tour then continues through Charlestown, where guests may see the USS Constitution and Bunker Hill Monument before leaving Boston for Lexington.

Lexington Battle Green and Historic Lexington

Lexington brings the tour directly into the events of the morning of April 19, 1775.

Important Lexington landmarks can include:

• Munroe Tavern
• Buckman Tavern
• Lexington Battle Green
• Hancock-Clarke House

At Lexington Battle Green, visitors stand at the historic common where British regulars and members of the Lexington militia confronted one another during the opening hours of the Revolutionary War.

Buckman Tavern is associated with Captain John Parker’s militia, while the Hancock-Clarke House connects the story with John Hancock, Samuel Adams, Paul Revere and William Dawes.

From Lexington to Concord

From Lexington, the journey continues toward Concord while following the geographic progression of the events of April 19.

The drive between the two towns is itself part of the historical experience, helping visitors understand how the British expedition, alarm riders and colonial militia moved through the communities west of Boston.

Wright Tavern and Concord Center

In Concord, Wright Tavern can be included as a brief historical stop before continuing toward the North Bridge.

The Revolutionary-era tavern is associated with political activity before the Revolution and with events surrounding the British expedition to Concord on April 19, 1775.

Old North Bridge

The centerpiece of the Concord portion is Old North Bridge, where colonial militia and British regulars exchanged fire during the morning of April 19.

The location became permanently associated with the opening of the American Revolution and with the phrase the “shot heard round the world.”

Visitors may also see the Minute Man statue and spend time exploring the North Bridge area before continuing through Concord.

Literary Concord

Concord’s history extends well beyond the American Revolution.

The town later became associated with some of the most important writers and thinkers in nineteenth-century America, including Ralph Waldo Emerson, Henry David Thoreau, Louisa May Alcott and Nathaniel Hawthorne.

Depending on interests and available time, the tour may pass literary landmarks including:

• Orchard House
• Ralph Waldo Emerson House
• The Wayside
• Concord’s Colonial Inn

An optional visit to Sleepy Hollow Cemetery and Authors Ridge may also be incorporated when time and mobility allow.

Who Is the Boston, Lexington & Concord Tour Best For?

This experience is particularly well suited to:

• American history enthusiasts
• Travelers interested in the American Revolution
• Families studying Revolutionary history
• Visitors who want more historical depth than a standard Boston sightseeing tour
• Travelers interested in combining Revolutionary and literary history

Learn more: Private Boston, Lexington & Concord Historical Tour

3. Private Plymouth Day Trip from Boston

Plymouth offers a different chapter of New England history.

While Lexington and Concord focus on the beginning of the American Revolution, Plymouth takes visitors further back into the story of early colonial New England, the Mayflower passengers and the development of Plymouth Colony.

The Private Plymouth Day Trip from Boston is generally an approximately 8-hour private chauffeured day trip.

This is different from the Boston and Lexington & Concord guided tours. The chauffeur provides transportation to Plymouth and between planned attractions, while passengers generally explore museums, historic sites and other attractions independently.

What Can You Visit on a Plymouth Day Trip?

A Plymouth itinerary may include:

• Plimoth Patuxet Museums
• Plimoth Grist Mill
• Plymouth Rock
• Mayflower II
• Cole’s Hill
• Pilgrim Hall Museum
• National Monument to the Forefathers
• Downtown Plymouth
• Plymouth waterfront

Plimoth Patuxet Museums

Plimoth Patuxet Museums is one of the major historical attractions in the Plymouth area and can form an important part of the day for travelers who want a deeper understanding of early colonial and Indigenous history.

Guests explore the museum independently while the chauffeur remains available with the vehicle.

Plymouth Rock and Mayflower II

Along the waterfront, travelers can visit Plymouth Rock and see Mayflower II, a reproduction of the seventeenth-century ship associated with the Mayflower story.

These waterfront landmarks can be combined with downtown Plymouth, Cole’s Hill and nearby historic attractions.

National Monument to the Forefathers

The National Monument to the Forefathers is another notable Plymouth landmark that may be incorporated into a private itinerary.

Its location away from the busiest part of the waterfront makes private transportation particularly useful when combining it with other Plymouth attractions.

Lunch and Downtown Plymouth

Guests may also allow time for lunch, walking along the waterfront, exploring downtown Plymouth or simply enjoying some unstructured time between historical attractions.

The amount of sightseeing that fits comfortably into the day depends on museum visits, admission times, lunch and how long passengers choose to spend at each location.

Who Is the Plymouth Day Trip Best For?

Plymouth is particularly well suited to travelers interested in:

• Pilgrim history
• The Mayflower story
• Early colonial New England
• Family-oriented historical attractions
• A full-day historical excursion from Boston

Learn more: Private Plymouth Day Trip from Boston

4. Private Newport Day Trip from Boston

Newport, Rhode Island provides a very different private day-trip experience from Boston.

Instead of concentrating primarily on Revolutionary or colonial history, Newport combines Gilded Age architecture, historic mansions, coastal scenery, waterfront dining and downtown sightseeing.

The Private Newport Day Trip from Boston is approximately 8.5 hours and includes private chauffeured transportation from Boston to Newport and between selected sightseeing stops.

As with Plymouth, passengers generally explore attractions independently while their chauffeur remains available with or near the vehicle.

The Newport Mansions

For many visitors, the Newport Mansions are the centerpiece of the day.

Common mansion choices include:

• The Breakers
• Marble House
• Rosecliff
• The Elms

A typical itinerary often prioritizes The Breakers and Marble House, with another mansion considered if ticket times, pace and interests allow.

Visiting fewer mansions leaves additional time for lunch, downtown Newport, the waterfront and coastal sightseeing.

Downtown Newport and Thames Street

Downtown Newport provides a relaxed contrast to the mansions along Bellevue Avenue.

Guests may spend time around:

• Thames Street
• The waterfront
• Downtown shops
• Restaurants and cafes
• Historic wharf areas

This part of the itinerary works particularly well for lunch, shopping or enjoying some flexible sightseeing time before returning to the vehicle.

Ocean Drive

A private Newport itinerary can also include a scenic drive along Ocean Drive.

The route offers views of the Atlantic Ocean, rocky shoreline, historic estates and some of Newport’s most attractive coastal scenery.

Because the chauffeur and vehicle remain available throughout the day, mansion visits, downtown sightseeing and Ocean Drive can be combined without relying on separate local transportation.

Who Is the Newport Day Trip Best For?

Newport is particularly well suited to travelers interested in:

• Gilded Age mansions
• Historic architecture
• Coastal scenery
• Waterfront dining
• Shopping and downtown sightseeing
• A relaxing full-day private excursion from Boston

Learn more: Private Newport Day Trip from Boston

What Is the Difference Between a Private Tour and a Private Day Trip?

The distinction between these services is important.

The Boston Private City Tour and the Boston, Lexington & Concord Historical Tour are guided sightseeing experiences that include historical narration.

The Plymouth and Newport experiences are primarily private chauffeured day trips. The chauffeur transports passengers between destinations and remains available with the vehicle, while guests independently explore museums, mansions, historic properties and other attractions.

This arrangement works particularly well for destinations where passengers may spend an hour or more inside an attraction and do not need a guide accompanying them throughout the visit.

Which Private Tour or Day Trip from Boston Should You Choose?

The best choice depends primarily on what you want to experience.

Choose the Boston Private City Tour if this is your first visit to Boston and you want to see the city’s major historic sites, neighborhoods and landmarks in a relatively short period of time.

Choose the Boston, Lexington & Concord Historical Tour if the American Revolution is your primary interest and you want to connect the political events in Boston with Lexington Battle Green and Concord’s Old North Bridge.

Choose the Plymouth Day Trip if you are interested in the Mayflower, Pilgrim history and early colonial New England.

Choose the Newport Day Trip if you prefer Gilded Age mansions, architecture, coastal scenery, waterfront dining and a more relaxed sightseeing day.

Travelers spending several days in Boston may choose more than one experience because the four itineraries represent very different aspects of New England history and culture.

Can These Private Tours and Day Trips Be Customized?

Yes. One of the primary advantages of private sightseeing is the ability to adjust the experience around the interests and pace of the passengers.

Depending on the service, travelers may choose to:

• Spend additional time at particular historic locations
• Reduce walking for travelers with limited mobility
• Concentrate on a specific period of history
• Adjust the balance between sightseeing and attraction visits
• Allow additional time for lunch or downtown exploration
• Skip locations that are not important to the party

Customization must remain within the reserved service period. Spending additional time at one location may reduce the time available elsewhere.

Additional service time may be available at the applicable hourly rate, subject to chauffeur and vehicle availability.

Are Museum and Attraction Tickets Included?

Unless specifically stated in the booking confirmation, admission to museums, historic houses, mansions, ships and other ticketed attractions should be considered separate from the tour or transportation service.

This is particularly important for destinations such as the Newport Mansions and major Plymouth attractions, where operating schedules and timed admission may affect how the itinerary is organized.

Travelers planning interior visits should consider current attraction schedules when arranging the day.

Do the Private Tours and Day Trips Begin in Boston?

These experiences are designed primarily for travelers staying in Boston and the surrounding area.

Pickup details are confirmed when the reservation is arranged. From there, the private vehicle remains dedicated to the party for the reserved service period, whether sightseeing within Boston or traveling to Lexington, Concord, Plymouth or Newport.

Private Sightseeing Without a Large Group-Tour Schedule

A private tour or chauffeured day trip allows travelers to experience Boston and nearby New England destinations without following the fixed schedule of a large sightseeing bus.

For one group, that may mean spending additional time discussing Revolutionary history at Lexington Battle Green. Another family may prefer more time at Plimoth Patuxet Museums. Visitors to Newport may choose a longer mansion visit or a relaxed waterfront lunch, while Boston City Tour passengers may want to concentrate more heavily on Beacon Hill, the Freedom Trail or Cambridge.

The common element across all four experiences is private transportation reserved for the passengers and an itinerary that can be adapted around their interests and available time.

Compare Our Four Private Boston Sightseeing Experiences

• Private Boston City Tour – approximately 4 hours of guided sightseeing in Boston and Cambridge.
• Private Boston, Lexington & Concord Historical Tour – approximately 6 hours following the Revolutionary story from Boston to Lexington and Concord.
• Private Plymouth Day Trip from Boston – approximately 8 hours of private chauffeured transportation for Plymouth’s colonial and Pilgrim attractions.
• Private Newport Day Trip from Boston – approximately 8.5 hours for Newport mansions, downtown, the waterfront and Ocean Drive.

Plan a Private Tour or Day Trip from Boston

Whether you want an introduction to Boston, a deeper exploration of Revolutionary history, a day in historic Plymouth or a private trip to Newport’s Gilded Age mansions and coastline, Boston Preferred Car Service can help arrange the experience around your party and sightseeing interests.

Choose the destination that best matches your visit, or combine several experiences during a longer stay in Boston.

Boston Preferred Car Service
Phone: +1-781-816-3851
Email: reservations@bostonpreferred.com