Rebels, Redcoats, and Remarkable Women—Boston Awaits

Boston is where America found its voice—and Paul Revere made sure it was heard. On the night of April 18, 1775, Revere rode through the darkened streets to warn the colonial militia that British troops were on the move. His midnight ride was more than a dash on horseback—it was a defining moment of courage, urgency, and American grit. Today, you can walk the very cobblestones he did, stand beside his modest home in the North End, and feel the pulse of a nation being born.

May 12 – 16, 2025
5 days / 4 nights

Overall Trip Highlights

• Freedom Trail Tour: Walk the iconic 2.5-mile path that tells the story of the American Revolution, featuring 16 historic sites including Paul Revere’s House and the Old North Church.
• Fenway Park Tour: Explore the oldest baseball stadium in MLB history, home to the Red Sox since 1912, and learn about its famous “Green Monster.”
• Liberty Clipper Cruise: Sail Boston Harbor on a tall ship, reminiscent of the 19th century, offering stunning views of the city skyline and historical sites.
• Martha’s Vineyard: Enjoy a day on this picturesque island known for its charming towns, lighthouses, and as a popular presidential vacation spot.
• Boston Common: Visit America’s oldest public park, established in 1634, and learn about its role in historical events such as the American Revolution.
• Boston Tea Party Ships & Museum: Participate in an interactive reenactment of the 1773 Boston Tea Party, a pivotal event leading to the American Revolution.
• Boston Public Library: Marvel at the grandeur of this historic library, established in 1848, featuring beautiful architecture and rare book collections.
• North End: Wander through Boston’s oldest residential community, known for its rich Italian heritage and delicious cuisine, including famous cannolis.
• Beacon Hill: Stroll through this historic neighborhood, famous for its narrow, gaslit streets and brick row houses, offering a glimpse into 19th-century Boston life.

Don’t just tour Boston & Martha’s Vineyard – Experience them!

This city isn’t just a backdrop—it is the story. From the Boston Tea Party to the first shots of the Revolutionary War, Boston is the cradle of American independence. The Freedom Trail winds through sites that shaped our democracy—Old North Church, Faneuil Hall, the Massachusetts State House—each corner whispering tales of rebellion, risk, and reslove.

When you visit Boston with Beatrice Bradley, you’re not just sightseeing—you’re stepping into the pages of history. The courage of Paul Revere and the brilliance of the Founding Fathers come alive in the lantern glow of Beacon Hill and the salt air of Boston Harbor. Come walk where liberty began—and write your own chapter in the spirit of those who dared to dream of freedom.

FUN FACT ABOUT THIS TRIP

Boston Common: Established in 1634, it is the oldest public park in the United States, originally used as a cow pasture and for public hangings.

First Public School: Boston is home to the nation’s first public school, Boston Latin School, founded in 1635. It still operates today and boasts famous alumni like Benjamin Franklin and John Hancock.

Martha’s Vineyard Island History: Martha’s Vineyard was named by the English explorer Bartholomew Gosnold in 1602 after his daughter Martha and the wild grapes (vineyards) he found growing there. The island is known for it’s rich maritime history and picturesque landscapes.

Itinerary Subject to Change 

Day One: Arrival Day: Echoes of the Past, Friendships of the Future

Welcome to Boston—a city where every brick and breeze holds a story. After arriving and checking into your boutique accommodations at the elegant Godfrey Hotel, take a moment to settle in and feel the city’s heartbeat. Step outside and you’ll find yourself surrounded by cobblestone charm, historic spires, and the quiet hum of a city that helped birth a nation.

As the day softens into evening, we’ll gather for a Welcome Dinner—a joyful celebration of new friendships and shared adventure. Laughter will rise over candlelight and clinking glasses as you begin to connect with your fellow travelers. The conversation flows easily—it always does when kindred spirits meet.

To close the evening, enjoy a gentle twilight stroll through Boston Common, the oldest public park in America. As gas lamps glow and shadows stretch across timeworn paths, you’ll feel the presence of the past walking beside you. This is more than a welcome—it’s a homecoming to history.

Highlights:

• The Godfrey Hotel Check-In: Relax in the stylish comfort of this centrally located, boutique gem.
• Welcome Dinner: A delicious, laughter-filled evening as you connect with your fellow adventurers.
• Evening Walk through Boston Common: Stroll beneath the twilight sky through the heart of historic Boston.

Fun Fact:
Boston Common was established in 1634, making it the oldest public park in America. It has hosted everything from British Redcoats to civil rights marches—and now, you.

Day Two: Walking in the Footsteps of Patriots

After breakfast, you’ll step out into the heartbeat of Boston and onto the legendary Freedom Trail—a 2.5-mile journey through the soul of the American Revolution. With a passionate guide leading the way, you’ll visit powerful landmarks like Paul Revere’s House, the Old North Church, Granary Burying Ground, and the bustling Faneuil Hall. Each stop reveals the grit and brilliance of the patriots who sparked a revolution and shaped a nation.

Lunch offers time to relax and reflect as you savor the flavors of the city, dining on fresh, local seafood. In the afternoon, take in the postcard charm of Beacon Hill, where gas lanterns still glow over cobblestone streets, before exploring the vibrant buzz of Quincy Market, filled with unique vendors and street performers.

By day’s end, you won’t just have seen history—you’ll have walked where it was made.

Highlights

• Freedom Trail Experience: Walk the full 2.5-mile trail and visit iconic sites such as Paul Revere’s House, Old North Church, Granary Burying Ground (resting place of Samuel Adams and John Hancock), Faneuil Hall, and the site of the Boston Massacre.

  • Why it matters: The Freedom Trail links 16 pivotal landmarks of the American Revolution. It’s not just a tour—it’s the backbone of Boston’s role in birthing a nation.

• Expert Historical Guide: A passionate local brings Boston’s revolutionary past to life, weaving storytelling with the spirit of liberty.

• Dining on Fresh Local Seafood: Savor a midday meal featuring classic New England flavors and coastal fare.

• Beacon Hill: Meander through one of Boston’s most picturesque neighborhoods, rich in colonial charm and timeless beauty.

• Quincy Market: Enjoy browsing artisan booths, sampling local specialties, and soaking in the energy of this 19th-century marketplace.

Fun Fact:
The Freedom Trail is a one-of-a-kind experience, blending architecture, artifacts, and true stories of rebellion into an unforgettable walk through America’s founding chapter.

Day Three: Island Whispers and Vineyard Breezes

This morning begins with a delicious breakfast at the George Howell Coffee Shop, where the aroma of roasted beans mingles with the soft hum of a city waking up. Soon after, you’ll board a private coach to the coast—passing through the scenic landscapes of Cape Cod en route to Falmouth. There, the Island Queen Ferry awaits, gliding you across the sparkling Atlantic toward the storied shores of Martha’s Vineyard.

The moment you step onto the island, time seems to slow. A private guided tour reveals the island’s layered beauty—from the dramatic sweep of Gay Head Cliffs to the whitewashed elegance of Edgartown Harbor Light. As you journey through the island’s beloved towns, you’ll feel the salty breeze, hear seagulls overhead, and understand why this place has captivated visitors for centuries.

In Oak Bluffs, enjoy a relaxed seaside lunch featuring fresh, local seafood before returning by ferry to the mainland. That evening, the adventure continues with a lively dinner at The French Quarter, where the spirit of New Orleans meets Boston’s hospitality in a celebration of bold flavors and new friendships.

Highlights

• Scenic Ferry Ride: Sail across Vineyard Sound aboard the Island Queen, soaking in the fresh salt air, glimmering ocean views, and anticipation of arriving on one of New England’s most iconic islands.
• Private Guided Tour of Martha’s Vineyard: Explore the island’s most treasured spots with a local expert. Marvel at the multicolored clay cliffs of Gay Head in Aquinnah, stroll through Edgartown’s cobblestone streets and elegant captain’s homes, visit the charming gingerbread cottages in Oak Bluffs, and take in sweeping views from the island’s picturesque lighthouses.
• Why Visitors Love It: With its natural beauty, unspoiled beaches, celebrity hideaways, and deeply rooted seafaring history, Martha’s Vineyard offers a unique blend of elegance, simplicity, and timeless charm that continues to inspire and enchant travelers from all walks of life.
• Lunch in Oak Bluffs: Savor coastal flavors at the Martha’s Vineyard Chowder Company, where fresh seafood and island atmosphere come together in a delicious, relaxed setting.
• Return to Boston: Unwind as the ferry carries you back across the water, the golden light of the afternoon casting reflections on the waves.
• Dinner at a Chef-Renowned Restaurant: Experience an unforgettable evening at one of Boston’s celebrated culinary destinations, where a visionary chef delivers an artful, locally inspired menu in a stunning setting.

Fun Fact:
Martha’s Vineyard was once a thriving whaling port, drawing sailors from around the world. Today, it remains one of New England’s most beloved retreats—where time slows down and the sea tells stories of centuries past.

Day Four: Boston in Full Color – A City Revealed

Begin your morning with a cozy breakfast at Café Bon Jour before boarding Boston’s iconic Hop On/Hop Off Trolley Tour—a charming, narrated ride that brings the city’s rich history to life at every turn. As the trolley winds its way through Boston’s neighborhoods, you’ll hear captivating tales of revolution, resilience, and rebirth told by expert local guides with just the right touch of wit and wonder.

Step off to explore the North End, Boston’s beloved Italian district, where aromas of fresh cannoli fill the air and Paul Revere’s legacy lingers on every street corner. Marvel at the elegance of Beacon Hill, stroll through the Boston Public Garden, and snap a photo at the original Cheers Bar, where “everybody knows your name.” Whether you’re captivated by historic churches, colorful row houses, or waterfront vistas, each stop deepens your connection to this unforgettable city.

As the day winds down, we’ll come together for a wonderful dinner at one of Boston’s favorite local restaurants—a time to relax, reflect, and share stories from a day of discovery and delight.

Highlights

• Hop On/Hop Off Narrated Bus Tour: Enjoy live storytelling from expert guides as you ride through Boston’s historic neighborhoods, learning the tales behind the sites that shaped America.

• North End: Boston’s oldest residential neighborhood, rich in Italian-American culture and home to Paul Revere’s House and the Old North Church, where lanterns signaled the British advance.

• Beacon Hill: Known for its Federal-style row houses and gaslit streets, this elegant district has been home to writers, politicians, and revolutionaries since the 1700s.

• Boston Public Garden: America’s first public botanical garden, established in 1837. Ride a swan boat or stroll beside willow-shaded paths once favored by 19th-century Bostonians.

• USS Constitution & Boston Navy Yard: Step aboard “Old Ironsides,” the world’s oldest commissioned warship still afloat, a symbol of naval victory from the War of 1812.

• Cheers Bar: Visit the bar that inspired the classic television show, located near Boston Common. It’s a light-hearted photo op and a nostalgic nod to pop culture rooted in Boston’s charm.

Fun Fact:
Boston’s Hop On/Hop Off Trolley covers over 100 points of interest in a single loop, making it one of the most enjoyable and informative ways to discover the city’s revolutionary heart.

Founder’s Note:
“This wasn’t just a sightseeing tour—it was a true experience. Riding that trolley, I laughed, I learned, and I saw Boston in a whole new way. It was one of the best times I’ve had in years.”
—Kim Kalan, Founder of Beatrice Bradley

Day Five: Departure Day 

As your journey in Boston draws to a close, enjoy a morning filled with reflection and a bit more adventure. After checking out of The Godfrey Hotel, savor one last breakfast at Café Bon Jour. Take advantage of free time for some last-minute shopping or exploring iconic spots like Newbury Street or Quincy Market, perfect for finding souvenirs or simply soaking in the city’s charm. Then, head to the airport, saying goodbye to new friends and this beautiful city.

Highlights

• Farewell Breakfast: Share a final meal with your travel companions at Café Bon Jour, reflecting on your adventure.
• Last-Minute Shopping: Explore the chic boutiques of Newbury Street or grab unique gifts from Quincy Market.
• Check-Out: Depart from The Godfrey Hotel and prepare for your journey home.
• Departure: Enjoy a smooth airport transfer and bid farewell to Boston.

Fun Fact: Newbury Street is often referred to as Boston’s “Rodeo Drive” for its high-end shops and charming brownstones!

Note: This itinerary serves as a general guide to what we will be doing, seeing, and eating, with the final version provided approximately two weeks prior. The published itinerary is an example and may be adjusted to include accommodations, tours, or restaurants of comparable quality to ensure the best experience.

***Itinerary subject to change