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

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.

Overall Trip Highlights

Freedom Trail Tour
Follow the famous 2.5-mile trail through 16 historic landmarks — from Boston Common to Paul Revere’s House and the Old North Church — and step back into the Revolutionary spirit that shaped America.

Fenway Park Tour
Go behind the scenes at America’s oldest Major League ballpark. Hear legendary stories of the Red Sox, walk in the footsteps of baseball greats, and see the iconic “Green Monster” up close.

Liberty Clipper Sunset Cruise
Set sail on a tall ship for a magical evening in Boston Harbor. Watch the city lights sparkle as the sun sets over the skyline — an unforgettable, picture-perfect moment.

Martha’s Vineyard Excursion
Escape to this world-famous island for the day. With a private guided tour, discover charming seaside villages, historic lighthouses, and breathtaking coastal views.

Hop-On Hop-Off Trolley Tour
See Boston from the comfort of a classic trolley. Explore vibrant neighborhoods and historic landmarks at your own pace with the freedom to hop on and off where you choose.

Itinerary Subject to Change 

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

Fly into BOS – Boston Logan International Airport by 3:00 PM – Our hosts will welcome you at the airport!

We will settle into our boutique accommodations in the heart of the city. Once everyone is checked in, we’ll kick things off with a Welcome Dinner, the perfect chance to meet your fellow travelers and start building friendships right away.

After dinner, we’ll take a relaxed evening stroll through Boston Common, the oldest public park in America, and soak in the atmosphere of this historic city under the twilight sky.

Highlights:

• 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 a leisurely breakfast at George Howell Coffee inside your hotel, your journey through revolutionary history begins. You’ll gather with your hosts and set off on foot to meet your expert guide for the Freedom Trail Tour, a 2.5-mile walk that immerses you in Boston’s pivotal role in the birth of a nation. With stops at legendary landmarks like Boston Common, the Old South Meeting House, Faneuil Hall, and Copp’s Hill Terrace, this tour brings the past vividly to life.

Lunch follows at a nearby French café, offering time to relax and refuel with a taste of European flair in the heart of Boston. After a midday break back at the hotel, the adventure continues with a guided private tour of Fenway Park, one of baseball’s most iconic stadiums and a symbol of Boston pride.

As the sun sets, your group will enjoy dinner nearby and reflect on a day filled with stories of revolution, resilience, and the enduring spirit of Boston.

Highlights

• Freedom Trail Experience:
  Walk the full 2.5-mile trail with a guide and explore all 16 historic landmarks, including Boston Common, the Old North Church, and Copp’s Hill Terrace—sites that define America’s revolutionary legacy.

• Why it matters:
  The Freedom Trail isn’t just a route—it’s a living thread through Boston’s role in sparking the American Revolution and shaping democratic ideals.

• Expert Historical Guide:
  A passionate local historian shares the drama and triumphs of the Revolution, bringing the people and places of the 18th century vividly into focus.

• Time to Reflect & Recharge:
  Enjoy a relaxed lunch and a chance to unwind back at the hotel before diving into the next chapter of your Boston experience.

• Fenway Park Tour:
  Go behind the scenes of “America’s Most Beloved Ballpark,” home to legends, lore, and the famous Green Monster.

Fun Fact:

The Freedom Trail is marked by a continuous red brick line—just follow it and you’re walking in the footsteps of history. It’s the only trail of its kind in the U.S. to unite so many revolutionary sites in one unforgettable walk.

Day Three: Trolleys, Treasures, and Tall Ships

Start your day with a delightful breakfast at Tatte Café, a Boston favorite known for its cozy charm and fresh morning fare. From there, you’ll set out to explore the city aboard a classic hop-on hop-off trolley tour, the perfect blend of comfort and discovery. With flexibility to stop and stroll, you’ll experience Boston’s most iconic neighborhoods and historic sites—each stop offering a new window into the city’s vibrant personality.

After a day of sightseeing, the group disembarks near the South Fish Pier for a peaceful waterfront walk, setting the stage for an early dinner along the harbor. Then, as the evening breeze rolls in, you’ll step aboard the Liberty Clipper, a majestic tall ship, for a sunset cruise around Boston Harbor. It’s the perfect finale to a day filled with movement, history, and stunning views.

The night wraps with a sweet treat stop at Ben & Jerry’s, a lighthearted way to end a day steeped in sights and stories.

Highlights

• Hop-On Hop-Off Trolley Tour:
  Experience Boston at your pace aboard an open-air trolley, with stops at landmarks like Beacon Hill, Boston Common, and the waterfront.

• Why it matters:
  This tour style combines freedom and guidance—giving you both structure and spontaneity to explore Boston’s iconic sites.

• Tatte Café Breakfast:
  Begin your day at a beloved local spot known for its artisanal offerings and beautiful interiors—a true taste of Boston mornings.

• Scenic Waterfront Walk:
  After sightseeing, enjoy a relaxing stroll along the historic South Fish Pier, soaking in views of the harbor and city skyline.

• Liberty Clipper Sunset Cruise:
  Board a historic-style schooner for a two-hour sunset sail, offering unforgettable views of Boston from the water and a sense of maritime adventure.

• Evening Treat at Ben & Jerry’s:
  Cap off the day with a scoop of something sweet and fun before making your way back to the hotel.

Fun Fact:

The Liberty Clipper is modeled after 19th-century schooners and offers an authentic sailing experience—no engines, just wind in the sails and Boston Harbor all around you.

Day Four: 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 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