Private Walking Tour of Freedom Trail and Little Italy

Boston , United States

Private Walking Tour of Freedom Trail and Little Italy

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About this experience

See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul Revere House, Copp's Hill Burying Ground, Old North Church, USS Constitution, Boston Common, Old South Meeting House, Old State House, Bunker Hill Monument and more! Listen to hilarious stories from Boston's past as you learn about the history of the area from a longtime resident, passionate historian, and former city employee. Tour includes a short walk through historic Little Italy.

Available options

Private Walking Tour of Freedom Trail and Little Italy

What's included

Professional Tour Guide

Detailed itinerary

Stop 1

Start the day in Boston Common, the oldest public park in the country. Listen to lesser-known stories told by the forgotten plaques and monuments of as you stroll this beautiful park.

Stop 2

Tour Boston’s most prestigious brownstone-lined neighborhood. Visit the “Most Photographed Street in North America”, featuring some of the original cobblestone. Stop by Louisburg Square, previously home to famous writers, today home to famous bankers and politicians.

Stop 3

Learn about the architecture and history of this famous building. Why is there a pine cone on top of the state house dome? What were the "King's Pines" and why did the pine tree end up symbolizing the American revolution?

Stop 4

Visit one of America's most historic cemeteries. Listen to stories of the American Revolution as you visit the graves of famous Founding Fathers Sam Adams, Paul Revere, John Hancock, and more

Visit Boston's oldest cemetery, home to the graves of John Winthrop and William Dawes. Hear about King's Chapel, Boston's first Anglican Church, which was deeply despised by the local Puritans.

Visit the site of the Old Corner Bookstore, one of the most prolific publishing houses in early America. This building was where the first run of several important works was released, including Walden, The Scarlet Letter, Battle Hymn of the Republic, and Midnight Ride of Paul Revere.

Stop 7

View the building where the Boston Tea Party started. Listen to the story of one of Colonial America's most famous rebellions. Hear how Sam Adams rallied the crowd to storm the ships in Boston Harbor and dump the tea in the water.

Stop 8

Learn about the "Cradle of Liberty," where Sam Adams gave his famous speeches that united Boston against the British. Learn about the quirky history behind this building's financial sponsor, Peter Faneuil.

Stop 9

See the oldest wooden building in downtown Boston, where Paul Revere lived for 20 years. Located on North Square, one of the oldest continually-inhabited areas of Boston, and former home to dignitaries such as Rose Fitzgerald Kennedy.

Learn about the immigrant past of Boston's North End through public artwork installed on North Square

Stop 11

See the Old North Church and learn all about the midnight ride of Paul Revere and the historical inaccuracies of the famous poem!

Stop 12

Visit Boston’s second oldest burying ground, taking in view of the harbor and Charlestown, as well as the USS Constitution and Bunker Hill Monument. Learn all about Boston’s part in the events of the American Revolution.

Visit the historic outlook, where you can see Bunker Hill, the Charlestown Naval Yard, and the site of the Great Molasses Flood

What's not included

Gratuities

Recommended to bring water

Lunch

Available languages

Guide guide

Reviews breakdown

Viator 5.0

1 reviews

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Tripadvisor 5.0

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Important information

Infants and small children can ride in a pram or stroller

Service animals allowed

Public transportation options are available nearby

Travelers should have at least a moderate level of physical fitness

Meeting point

Look for the Boston Common Visitors Center located in the Boston Common part. Address is 139 Tremont St, Boston, MA 02111 .

About Boston

Boston, one of the oldest cities in the United States, is rich in history, culture, and education. Known for its significant role in the American Revolution and its prestigious universities, Boston offers a unique blend of historic charm and modern vibrancy.

Top Attractions

Freedom Trail

A 2.5-mile (4 km) walking route that passes 16 locations significant to the history of the United States, including churches, meeting houses, burying grounds, museums, and historic markers.

Historical 3-4 hours Free to walk the trail; individual attractions may have admission fees

Fenway Park

Home to the Boston Red Sox, Fenway Park is the oldest ballpark in Major League Baseball and a must-visit for sports fans and history buffs alike.

Sports/Historical 1-3 hours (tour or game) Tour: $20-$25; Game tickets: $30-$200+

Boston Common

America's oldest public park, Boston Common is a central gathering place for both locals and visitors, offering green spaces, walking paths, and seasonal activities.

Parks/Historical 1-2 hours Free (Swan Boats: $4-$5 per ride)

Museum of Fine Arts (MFA)

One of the most comprehensive art museums in the world, the MFA houses nearly 450,000 works of art, ranging from ancient Egyptian to contemporary.

Museum 2-4 hours $27 (adults), free for children under 17

Boston Harbor Islands National Recreation Area

A group of islands in Boston Harbor offering outdoor recreation, historic sites, and stunning views of the city skyline.

Nature/Historical Half-day to full-day trip $5-$15 per person, depending on the island and activities

Must-Try Local Dishes

Clam Chowder

A creamy, hearty soup made with clams, potatoes, onions, and sometimes bacon or salt pork. Boston-style clam chowder is typically made with milk or cream and is served with oyster crackers.

Soup Contains dairy and sometimes pork; vegetarian and vegan versions are available at some restaurants.

Lobster Roll

A buttered, toasted split-top roll filled with lobster meat, usually dressed with mayo or butter. Some versions include celery or other vegetables for added crunch.

Sandwich Contains shellfish and may contain dairy or eggs; gluten-free buns may be available at some restaurants.

Boston Cream Pie

A layered dessert consisting of sponge cake filled with custard or cream and topped with chocolate glaze. It's the official dessert of the Commonwealth of Massachusetts.

Dessert Contains dairy, eggs, and gluten; vegan and gluten-free versions may be available at some restaurants.

Oysters

Boston is known for its fresh oysters, which can be found at many seafood restaurants and raw bars. They are typically served on the half-shell with various toppings or sauces.

Appetizer Contains shellfish; vegan and vegetarian options may be available at some restaurants.

Popular Activities

Hiking in the Blue Hills Reservation Kayaking or paddleboarding in the Charles River Biking along the Charles River Esplanade Rock climbing at Brooklyn Boulders Picnicking in the Boston Common or Public Garden Strolling along the Charles River Esplanade Enjoying a spa day at one of Boston's many luxury spas Reading a book at the Boston Public Library

Best Time to Visit

Late spring to early fall (May to October)

This is the best time to visit Boston for pleasant weather and outdoor activities. The city is vibrant with festivals and outdoor events.

10°C to 25°C (50°F to 77°F) 50°F to 77°F

Practical Information

Language

Official: English
Widely spoken: Spanish, Chinese, Portuguese, French, Italian
English: Widely spoken

Currency

US Dollar (USD)

Time Zone

Eastern Standard Time (EST) (UTC-5) or Eastern Daylight Time (EDT) (UTC-4) during daylight saving time

Electricity

120VV, 60HzHz

Safety Information

Overall Safety Rating: Generally safe

Boston is generally a safe city for travelers, with a low crime rate and a strong police presence. However, as with any major city, it's important to be aware of your surroundings and take precautions to ensure a safe and enjoyable visit. Some areas of the city, such as certain neighborhoods in Dorchester, Roxbury, and Mattapan, have higher crime rates and should be avoided, especially at night.

Important Precautions:

• Be aware of your surroundings and keep valuables secure, especially in crowded tourist areas and on public transportation
• Use licensed taxis or rideshare services, and always check the fare before starting your journey
• Be cautious of strangers approaching you with petitions or surveys, and avoid sharing personal information

Getting there

By air

Logan International Airport • 3 miles (5 km) from city center

By train

South Station, North Station

By bus

South Station, Logan Airport

Getting around

Public transport

The MBTA subway system is efficient and affordable, with four main lines (Red, Blue, Green, and Orange) connecting major attractions and neighborhoods.

Taxis

Available • Apps: Uber, Lyft

Rentals

Car, Bike, Scooter

Neighborhoods

Downtown/Financial District Back Bay North End South End Fenway-Kenmore Beacon Hill

Day trips

Salem

16 miles (26 km) from Boston • Half-day to full-day trip

A historic coastal city known for its connection to the Salem Witch Trials of 1692. Salem offers a mix of historic sites, museums, and waterfront activities.

Lexington and Concord

10-15 miles (16-24 km) from Boston • Full-day trip

Two historic towns that played significant roles in the American Revolution. Lexington and Concord offer a mix of historic sites, museums, and scenic walking trails.

Cape Cod

60-80 miles (97-129 km) from Boston, depending on the destination • Full-day trip or overnight stay

A popular summer destination known for its beautiful beaches, charming coastal towns, and outdoor recreation. Cape Cod offers a mix of relaxation and adventure.

Festivals

Boston Harbor Hotel Chowder Festival • October (annual) Boston Pride • June (annual) Boston Film Festival • September (annual)

Pro tips

Visit the Freedom Trail early in the morning or on a weekday to avoid crowds and enjoy a more peaceful experience
Take advantage of free or discounted admission days at museums and other attractions, such as the Museum of Fine Arts' free Wednesday evenings or the Boston Public Library's free exhibits and events
Explore Boston's diverse neighborhoods, each with its own unique character, history, and attractions
Try local specialties, such as clam chowder, lobster rolls, and Boston cream pie, at historic and iconic eateries like Union Oyster House, Neptune Oyster, and Mike's Pastry
Attend a Red Sox game at Fenway Park, one of the most iconic and historic baseball stadiums in the world