Historic Boston and Martha's Vinyard

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

Walk the Freedom Trail – Follow the red-brick path to 16 Revolutionary sites like Paul Revere’s House and Old North Church.
Tour Fenway Park – Step inside the legendary home of the Red Sox and meet the iconic Green Monster.
Sail on the Liberty Clipper – Cruise Boston Harbor aboard a majestic tall ship with skyline and history all around.
Escape to Martha’s Vineyard – Relax on a storybook island dotted with lighthouses, beaches, and charm.
Stroll Boston Common – Explore the oldest public park in the U.S.—once a grazing field, now a landmark of liberty.
Visit the Boston Public Library – A stunning blend of history, art, and architecture—books optional!
Explore the North End – Savor Italian flavors, cobblestone streets, and the best cannolis in Boston.
Wander Beacon Hill – Picture-perfect streets, gaslit lamps, and timeless New England charm.

Multiple Departure Dates Available
September 22 – 26, 2025
May 11-15, 2026
August 29 – September 2, 2026

5 Days / 4 Nights

Group Size: 12 Guests
Your BB Hostesses: 2 Fabulous Hosts

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.

Single Occupancy	Double Occupancy
$3,950	$2,950
Private Room with Private Bath	Shared Room, Separate Beds, Shared Bath
Deposit Due at Time of Booking: $250 for Domestic/$500 for International	Deposit Due at Time of Booking: $250 for Domestic/$500 for International
Book Single Occupancy September 22 – 26, 2025 – SOLD OUT May 11-15, 2026 – Available August 29 – September 2, 2026 – Available Dates Sold Out? Join the Waitlist	Book Double Occupancy September 22 – 26, 2025 – SOLD OUT May 11-15, 2026 – Available August 29 – September 2, 2026 – Available Dates Sold Out? Join the Waitlist

Beatrice Bradley Experiences are All Inclusive. What does that mean?

Airport Group Transfers: Seamless airport pickups and drop-offs by our friendly hostesses, ensuring a smooth start and end to your adventure.
Dedicated BB Hostess: Travel with peace of mind knowing a dedicated Beatrice Bradley hostess will be with you throughout the trip, ensuring every aspect of your journey is unforgettable.
Full Dining: Enjoy 2-3 daily meals carefully selected to reflect the local cuisine, inclusive of all tips. Whether it’s a quick breakfast or a sumptuous dinner, we’ve got it all covered.
Unique Accommodations: Stay in boutique hotels or unique properties that are handpicked for their charm and comfort, providing an authentic and intimate experience.
Curated Activities: We find the BEST of the best tours. Making the absolute most out of our time.
Included Gratuities: Tips for tour guides, meals, and transportation are all taken care of. We ensure that those who make your trip special are rewarded, without you needing to worry about the details.
Transportation: All transportation is included throughout the experience, from airport pickup to your final drop-off.
You won’t see “Free Days” on our itineraries: Our trips are made for a balanced experience. We carve out time to bond, laugh, shop and explore but we will never just send you out on your own and say “good luck” we do everything together or smaller group breakouts.

With Beatrice Bradley, every detail is meticulously planned to ensure you have a memorable and carefree travel experience. Join us and discover the joy of true hassle-free travel!

We Offer Flex-Pay! What is that?

Flexible Payments at Your Fingertips: You can use your invoice to pay any amount you choose, as frequently as you wish, until the full payment deadline.

Want to make a payment? Click “Review and Pay” on your invoice whenever you’re ready.

Pay Your Way: You can adjust the payment amount by selecting “Edit Amount,” allowing you to manage your budget flexibly.

Final Countdown: Ensure everything is paid up 60 days prior to your trip for domestic and 90 days prior for international. Don’t worry, we’ll send you reminders! If there’s any remaining balance, we’ll automatically process it, allowing you to focus on the excitement of your upcoming adventure!

Arrival Information	Departing Information
BOS – Boston Logan Airport	BOS – Boston Logan Airport
Must arrive before 3:00 PM	Depart at your convenience

There will be taking walking tours, taking a Fenway Park tour so there may be walking and going up and down steps and we will be taking busses and going on a boat and also a ferry to Martha’s Vineyard. We encourage you to do as much activity as you are able. There is never any pressure nor requirement to participate in all activities. If you need to take a break, please let your hosts know.

Connie Hart, and Karen Schluchter are set to be your fabulous hosts—but stay tuned, as our dazzling hostess lineup is always subject to a little delightful change!

As your hostesses, we understand that traveling solo can be intimidating, but rest assured, making you feel welcomed and comfortable is our top priority. Our experiences are designed for building new and lasting friendships in a warm and welcoming environment.

From the moment you arrive until we bid you farewell, we’ll be right by your side. We meticulously handle all the details and manage the logistics seamlessly behind the scenes, ensuring your journey is truly unique and worry-free. While we aren’t local experts or tour guides, we work with a network of local professionals carefully selected for each location to enrich your experience.

Read more about our Hostesses Here

Thinking about joining us?

If you’re on the fence or have any questions, we’re here to help. Simply fill out this form to get in touch. We can’t wait to assist you in planning an unforgettable adventure!

If you have any immediate questions, please feel free to get in touch: 763-864-8291 | Lindsay@bbgage.com

Ready to book? We’re happy to have you!

Book Here

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:

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: Boston’s Bold Beginnings & Legendary Landmarks

Today begins with a relaxed, self-paced breakfast and a moment to enjoy the morning energy of Boston. Afterward, you’ll step into the city’s revolutionary past with a guided walking tour along the famous Freedom Trail—a 2.5-mile journey that connects 16 of Boston’s most iconic historic landmarks.

From Boston Common to the Old North Church, and Paul Revere’s House to the Granary Burying Ground, you’ll walk in the footsteps of the patriots who shaped a nation. With a passionate local guide leading the way, each site becomes a powerful story of courage, conviction, and transformation.

After your immersive dive into history, you’ll pause to enjoy a delicious lunch and a chance to reflect with your fellow travelers.

In the afternoon, you’ll have time to relax and recharge before heading out for one of Boston’s most iconic experiences—a guided tour of the legendary Fenway Park. From the Green Monster to the storied halls of this historic stadium, you’ll get a behind-the-scenes look at one of America’s favorite pastimes.

To close out the day, gather for a memorable dinner with great conversation, delicious food, and the kind of laughter that only happens when new friends become travel family.

Highlights:

Freedom Trail Walking Tour: A guided journey through all 16 official landmarks of Boston’s revolutionary story.
Historical Immersion: Walk the very streets that helped shape the founding of the United States.
Iconic Fenway Park Experience: A behind-the-scenes look at one of the most legendary ballparks in the world.
Shared Meals & New Friendships: Moments of connection that make the journey even more meaningful.

Why it matters:
Today blends history, culture, and connection, offering you the chance not only to explore Boston’s past but to create lasting memories with the women beside you

Old South Meeting House - Boston - Massachusetts

Sign on the fence of Granary Burying Ground in Boston

Day Three: Explore Martha’s Vineyard

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 to Martha’s Vineyard: 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.
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

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: A Colorful Cruise Through Boston’s Charm

Today is a full celebration of everything that makes Boston unforgettable—iconic sights, coastal beauty, and sweet surprises.

The day begins with breakfast at a beloved local café, where fresh pastries and warm coffee set the tone for a day of adventure. After fueling up, you’ll head out to explore the city aboard Boston’s Hop On/Hop Off Trolley Tour—a narrated journey through the heart of the city’s most historic and picturesque neighborhoods. With live storytelling and the freedom to explore at your own pace, this experience brings the soul of Boston to life.

Take in the charm of Beacon Hill, the energy of the North End, and the elegance of the Public Garden, all from the comfort of the trolley—with time to hop off, snap photos, and savor each stop.

In the afternoon, we’ll step off at the South Fish Pier for a scenic stroll along the waterfront before gathering for an early dinner. It’s the perfect chance to relax and reflect on the sights and stories of the day while enjoying a delicious meal in good company.

But the day isn’t over yet—just as the sun begins to set, you’ll board the stunning Liberty Clipper for a sunset sail around Boston Harbor. With the city skyline glowing in the background and the sea breeze on your face, it’s a moment of pure magic.

To top it all off, we’ll end the evening with a fun stop for ice cream at Ben & Jerry’s—a sweet and lighthearted way to close a picture-perfect Boston day.

Highlights:

Hop On/Hop Off Trolley Tour: Discover Boston’s most iconic neighborhoods with expert narration and endless charm.
Scenic Waterfront Walk: Take in the harbor views as you make your way to a relaxing early dinner.
Sunset Sail on the Liberty Clipper: Cruise the Boston Harbor aboard a classic tall ship as the sun dips below the skyline.
Evening Treat at Ben & Jerry’s: Because no great day should end without dessert!

Why it matters:
Today captures the essence of Boston—historic, scenic, and full of heart. From the city’s storied streets to its sparkling harbor, every step brings you closer to the magic that makes this city so unforgettable.