Welcome to Boston!
American history isn’t complete without a visit to perhaps the most impactful city from Colonial America. If you want to experience where it all started, Boston is a must-see. Students watch their history books come to life as they wander through the North End, walk the deck of the USS Constitution, and explore the battlefields of Lexington and Concord. Boston, a city steeped in history, holds profound significance through its pivotal role during the American Revolution.
Arrive at your boutique hotel located in the heart of Boston. Location in a prime spot, this hotel offers easy walking distance to many of the city's most famous attractions.
The Private Walking Tour of the First Half of the Freedom Trail offers a personalized journey through Boston’s colonial history, exploring landmarks like Boston Common, the Massachusetts State House, and the site of the Boston Massacre. Led by a knowledgeable guide, this immersive experience brings to life the pivotal events and figures that shaped the American Revolution.
Note: The Freedom Trail is divided into two separate visits. This additional time allows for a more informative and enjoyable experience.
Eat dinner at the oldest restaurant in Boston and the oldest restaurant in continuous service in the United States - the doors have always been open to diners since 1826. This historic restaurant is known for its chowder and New England seafood dishes.
The Boston Tea Party stands as an iconic moment in American history, symbolizing the colonists' defiance against British taxation and their fight for independence. On December 16, 1773, a group of colonists dressed as Mohawk Indians boarded three ships and dumped 342 chests of tea into Boston Harbor as a protest against the Tea Act. This act of rebellion had far-reaching consequences and played a significant role in escalating tensions between the colonies and Great Britain.
The Boston Tea Party Museum, located at the site of the 1773 event, has replica merchant ships, excellent interactive exhibits and displays, and wonderful 'in character' guides.
The Second Half of the Freedom Trail continues the journey through Boston’s revolutionary past, featuring historic sites like Paul Revere’s House, Old North Church, and the Bunker Hill Monument. With expert commentary and engaging storytelling, this tour deepens the understanding of the city’s critical role in America’s fight for independence.
Note: The Freedom Trail is divided into two separate visits. This additional time allows for a more informative and enjoyable experience.
Since 1926, this pizzeria has been greeting guests in the North End with a hearty "Welcome to Boston's Original Pizzeria!". For over three generations this delicious brick oven pizza has been a Boston staple.
Even though the battle actually occurred on Breed's Hill, the Battle of Bunker Hill was a significant conflict between the Red Coats and Patriots. This monument stands as a tribute to the Colonial soldiers who fought in this battle and defeated the British.
The USS Constitution holds the distinction of being the world's oldest ship still afloat. Launched in 1797, it is one of the original six frigates of the United States Navy. When on board the USS Constitution, you will have the chance to explore below deck and talk with active duty US Navy sailors that are assigned to the ship.
Enjoy dinner at a waterfront restaurant located in Boston's Seaport district. Known for their pasta, steaks, and seafood, this restaurant has an elegant dining room that looks over the harbor.
Visit the battlefields and historic towns of Lexington and Concord. This is the place where the 'shot heard around the world' was fired in 1775.
The Battle Road Trail links historic sites from Concord's Meriam’s Corner to Lexington's eastern boundary, tracing the original route where Colonial Militia and British Regulars clashed in 1775.
Starting in Cambridge, return to Boston and experience the city from a fresh perspective with a relaxing bike ride along the Charles River.
The Boston Red Sox stand as one of the league's oldest and most loved baseball teams. The Red Sox play at Fenway Park, the oldest active Major League Baseball stadium. Rally behind this iconic team and enjoy America's favorite pastime!
Please Note:
The sample itinerary and budget provided are based on a specific number of participants and chaperones. Final pricing per person will vary depending on your group size and any adjustments made to the itinerary. Please keep in mind that prices may fluctuate depending on travel dates, seasonality, and other factors.
Please email us at [email protected] or call us at 512.596.1642 for more information.
All of our trips are fully customizable - this sample itinerary is simply a starting point to give you a sense of what is possible! We are happy to tailor every detail to fit your group’s unique needs, interests, and preferences.
Group travel can be a difficult and frustrating experience. The group is only as fast as the slowest participant, and that is why our clients spend most of their time in Chaperone Groups. These small groups consist of roughly 4-5 students and 2-3 adults, and move much more efficiently (and happily!) through the cities, allowing students to focus on their unique interests. Keeping entire groups together while following a yellow umbrella around cities (‘amoeba style’) creates missed opportunities and makes unfortunate use of valuable time.
The beauty of any school trip is the opportunity for the student to build self-confidence, problem solve, and learn how to navigate in a new environment. The adults are present to help keep students safe, but otherwise should ‘lead from behind’. At Kairos Tours we focus heavily on student leadership and responsibility for their trip experience.
Is there a minimum number of guests required for this trip?
There’s no minimum number of participants required, but please note that the fewer people in the group, the higher the price per person. Larger groups help keep individual costs lower by sharing fixed expenses like transportation and guides.
What information will be provided before the trip?
Each traveler will receive a complete, dynamic itinerary that includes travel logistics, hotel details, tours, entrance information, meeting points, and more—everything you need to feel fully prepared.
Will there be a group meeting before departure?
Yes! We’ll schedule a pre-trip meeting (either in person or via Google Meet) to go over final details, answer questions, and ensure everyone is ready and excited.
Does Kairos Tours provide a Tour Director?
A Tour Director can be arranged to accompany your group upon request. Please note this may affect the overall cost of the trip.
Will the itinerary change from what’s currently listed?
Kairos Tours will make every reasonable effort to provide this trip in accordance with the descriptions provided. Although it is unlikely that we will have to make any changes to your reservation or cancel confirmed reservations, we reserve the right to do so should it become necessary or advisable, in our sole discretion. We’ll always prioritize the best possible experience for your group!
Are trip prices guaranteed?
All pricing is based on current estimates and subject to change due to factors like group size, travel dates, currency exchange rates, and seasonal variations.
Are meals included in the trip price?
Lunches and dinners are typically not included in the trip price, allowing for flexibility and the opportunity to explore local dining options. Personal incidentals, such as snacks, souvenirs, and optional activities, are also the responsibility of each traveler.
What if there are unexpected delays or issues?
Kairos Tours is not responsible for costs or disruptions resulting from circumstances beyond our control, such as flight delays, changes or cancellations, injuries, weather, war, natural disasters, strikes, social discourse, pandemics, etc., and/or other unforeseeable matters.
My name is David Mebane and I am a lifelong traveler that experienced my first international trip as a 2nd grader, and I haven’t stopped since. I founded Fat Tire Tours in Paris, France in 1999 and love showing people around the City of Light. That passion has grown to include other incredible destinations around the globe, and is the genesis for Kairos Tours. I don't know every destination on the globe, but I do know several well, and I love to take people with me to create experiences and memories that last a lifetime.
I live in Austin, Texas with my wife Kelly and our son Weston and daughter Caroline. However, we spend as much time as we can elsewhere since there is nothing better than an adventure with family and friends.
Founded in 1630 by English Puritans, Boston, Massachusetts is one of the oldest cities in the United States, and a place where American ideals of liberty, education, and resistance first took root. The city was established on the Shawmut Peninsula by John Winthrop and his followers, who sought to build a "city upon a hill" - a shining example of moral society. Boston’s early years were shaped by religious discipline, tight-knit governance, and a fierce independence that would soon make it a catalyst for revolution.
From the beginning, Boston was a city of firsts: it opened the first public school in America (Boston Latin School, 1635) and the first university (Harvard College, 1636). It quickly grew into the intellectual and economic hub of New England, trading with Europe and the West Indies while anchoring a colonial population that would soon demand more than mercantile prosperity - it would demand freedom. The seeds of revolution were planted early in Boston’s cobbled streets, where colonial frustration over British taxation and military occupation began to boil.
The 18th century saw Boston at the heart of political resistance. Events such as the Boston Massacre (1770), where British troops killed five unarmed colonists, and the Boston Tea Party (1773), a bold protest against unjust taxation, positioned the city as the cradle of the American Revolution. Figures like Samuel Adams, Paul Revere, and John Hancock emerged as national icons, and local taverns became de facto revolutionary headquarters. When war broke out, the first major victory came here: in 1776, General George Washington forced British troops to evacuate the city after fortifying Dorchester Heights with captured cannons.
Following independence, Boston evolved from a revolutionary town to a booming urban center. The 19th century brought rapid industrialization, maritime commerce, and waves of immigration. The city became a hub of abolitionist activism, home to leaders like William Lloyd Garrison and Frederick Douglass, and a haven on the Underground Railroad. Meanwhile, Boston welcomed tens of thousands of Irish immigrants, especially during the Potato Famine, transforming the city’s demographics and politics. Later, Italian, Jewish, and Eastern European communities would also leave indelible marks on its cultural fabric.
Boston’s physical shape changed as much as its people. Vast land reclamation projects filled in the Back Bay and expanded neighborhoods like South Boston and Charlestown. The city modernized with new railways and bridges, and in 1897, Boston opened the country’s first subway. However, tensions remained: economic inequality, discrimination against immigrant groups, and clashes between old and new Bostonians sparked both progress and strife.
By the mid-20th century, Boston found itself grappling with both decline and transformation. The busing crisis of the 1970s, a court-mandated effort to desegregate schools, led to widespread unrest, especially in areas like South Boston, exposing deep racial divisions. Many residents moved to the suburbs, leaving inner-city neighborhoods in decline. But the city rebounded in later decades, buoyed by its unmatched concentration of colleges, hospitals, and research centers. Anchored by institutions like MIT, Harvard, and Mass General, Boston became a global leader in biotech, education, and healthcare.
The turn of the 21st century brought new challenges and opportunities. The ambitious Big Dig project buried the central highway beneath downtown, uniting neighborhoods long divided by asphalt. It also reshaped the urban landscape, giving rise to the Rose Kennedy Greenway and sparking a new era of civic pride. Meanwhile, neighborhoods like Seaport, Roxbury, and Jamaica Plain saw waves of gentrification, raising both property values and concerns about displacement.
Though not a capital city, Boston is in many ways the intellectual capital of America, a place where ideas are born, debated, and brought to life. Its residents - from students and scientists to longshoremen and artists - continue to push the boundaries of innovation and social change. It is a city proud of its layered identity: revolutionary birthplace, immigrant melting pot, academic mecca, and vibrant urban center.
Today, Boston is a place where you can walk the Freedom Trail through centuries of history, catch a game at Fenway Park, ride a streetcar through diverse neighborhoods, or dine in a high-tech lab-turned-restaurant. At once historic and forward-looking, Boston is a city that remembers where it came from - and never stops evolving.