🎯Past to Present Pathways: A Boston Urban Adventure (October 16 - October 22, 2027)

Boston has a way of making history feel unusually close. It is there in the crooked streets, the harbor views, the old brick buildings, and the layers of stories that still shape the city today. Past to Present Pathways is designed as a chronological journey through that history, beginning with the deeper roots of the region and moving through early contact, the Salem trials, the American Revolution, and the people and places that helped shape what came next. Rather than racing from landmark to landmark, we will take the time to understand how each chapter connects to the next and why these stories still matter.

The week also leaves plenty of room to simply enjoy Boston and the surrounding region. We will take in Boston Harbor, spend a full day in Salem, walk the Freedom Trail from the heart of downtown into Charlestown, and step into the stories of Lexington and Concord before slowing things down at Orchard House and Walden Pond. Along the way, there will be time to browse, eat well, notice the details, and enjoy the city at a pace that feels thoughtful rather than rushed. By the end of the week, the goal is not just to have seen Boston, but to feel like you understand the story of the place a little differently — and to have shared that experience with a small group of women along the way.

✨This trip is built for easy to moderate walking with flexible pacing. We’ll cover a lot of ground, but we’ll do it in a way that feels human. Some days are bigger story days with more time on our feet, especially the Freedom Trail and Salem, while other moments are intentionally slower so the history has time to land. Expect brick sidewalks, cobblestones, a few stairs, and plenty of chances to pause, browse, and take it all in.

Please pack with layers and comfortable walking shoes in mind. Mid-October in Boston can bring crisp fall days, cooler evenings, wind, and the occasional damp stretch, so flexibility is key. A light rain jacket, small day bag, and a comfortable “city-walk” mindset will make the week much easier and more enjoyable. Christine will send detailed packing suggestions in the months and weeks leading up to the trip.

What’s Included: All meals and snacks during the core trip, including hotel breakfasts (or breakfast elsewhere if we choose), lunches, and dinners, plus non-alcoholic drinks throughout the week such as water, coffee/tea, and soft drinks. One choose-your-own lunch at Quincy Market is on your own so everyone can pick what sounds best. All admissions, tours, and experiences listed in the itinerary are included, along with required tickets and entrance fees. Airport transfers are included, with timing coordinated around arrivals and departures, plus private group transportation throughout the week. Full itinerary planning, hosted guiding

throughout the trip, and a shared photo gallery after we return home are also included.

Not included: Airfare to and from Boston, and any lodging or meals outside the official trip dates, including anything before group pickup on October 16 or after checkout on October 22, unless you have arranged an optional early arrival or post-trip add-on. Meals outside the official trip itinerary are on your own unless otherwise noted. Quincy Market lunch is on your own. Personal incidentals, alcoholic beverages, souvenirs, and any optional add-on experiences not listed in the itinerary are not included.

Note: This itinerary is subject to change based on weather, road conditions, ticket availability, and group needs. We will always prioritize safety, a smooth flow, and the best possible experience. Listed experiences and planned routing may shift slightly as needed.

About Your Host & Local Guides:

Christine Baldwin serves as your trip host and retreat-style facilitator, shaping the overall flow of the week, coordinating logistics, and creating space for connection and reflection while keeping the experience grounded and real. Local guides and licensed operators may be included where helpful or required for specific experiences and tours.

🪶✨SMALL GROUP EXPERIENCE - max 6 women ✨

This expedition is designed for women who want a meaningful, story-rich adventure at a human pace. With a group this small, the experience stays personal and flexible - we can linger when something lands, move efficiently when it matters, and stay connected without feeling swallowed up by the crowd. Both shared and private room options are available, so guests can choose the lodging style that works best for them.

A full itinerary and pre-arrival guide will be sent after booking, along with a waiver and guest preference form. All guests must return a signed waiver to finalize participation.

💰Payment Plan

To reserve your spot, a $100 deposit is collected through WeTravel at checkout. This deposit holds your spot on this small-group experience.

• $100 deposit due upon booking

• Equal monthly payments begin October 16, 2026

• Payments will continue monthly through September 16, 2027

• Beginning October 16, 2026, the standard deposit will change to 10% of the trip price

• Full payment terms will be included at checkout on the WeTravel site. 

Expedition Sisterhood will always do its best to resell unused spots and issue partial refunds, when possible, should plans change unexpectedly.

🌿 Grace Period

Guests may cancel within 7 calendar days of booking for a full refund, including the deposit, if the waiver and guest agreement have not yet been signed.

Once the waiver is signed or the 7-day window has passed, whichever comes first, the deposit becomes non-refundable, and the cancellation terms below apply.

This grace period gives you time to fully review the experience and ask any questions before finalizing your commitment.

❗ Cancellation Policy

• The deposit becomes non-refundable after the grace period

• Cancellations made more than 30 days before the trip may be eligible for a partial refund based on what has already been paid or reserved on your behalf

• Cancellations within 30 days of the trip are non-refundable unless your spot can be filled by another guest

We believe in transparency and fairness. If you need to cancel, we’ll work with you to resell your spot whenever possible and minimize your financial loss.

Today our Boston chapter begins, with arrivals into Boston Logan International Airport (BOS) and coordinated transportation to our hotel on the harbor. We’ll settle in at Residence Inn by Marriott Boston Harbor on Tudor Wharf, giving everyone a little time to unpack, breathe, and ease into the week.

Once we’re ready, we’ll head out for a relaxed waterfront walk through the Charlestown Navy Yard, pausing near USS Constitution and continuing toward Paul Revere Park for those first harbor and skyline views. It’s an easy introduction to the city and a place we’ll return to later in the week with much more of Boston’s story behind us.

Tonight, we’ll gather around the table at Warren Tavern for our Welcome Dinner, then return to the hotel for a short Orientation Circle. Nothing heavy — just a chance to settle in, get comfortable with the week ahead, and begin getting to know the women we’ll be sharing it with.

After breakfast, we’ll step into the energy of Harvard Square, beginning with a relaxed walk through Harvard Yard and a little time to take in one of the most recognizable university settings in the country.

Late morning brings a grounding visit to the Harvard Peabody Museum of Archaeology & Ethnology, helping place Boston’s story within a much longer human timeline before we move into the chapters ahead. We’ll pause for an easy lunch in Harvard Square, giving ourselves a genuine break without making the day feel rushed.

In the afternoon, we’ll slow down inside the Isabella Stewart Gardner Museum, where the art, architecture, gardens, and extraordinary central courtyard make the museum an experience all its own. If weather and energy cooperate, we’ll add a gentle stroll through the Public Garden and Back Bay before heading back to the hotel.

Tonight is one of those classic Boston moments: dinner at Beacon Bistro at View Boston, paired with time on the observation levels for sweeping views across the city — whether we catch the last light of day or watch Boston begin to glow after dark.

Today begins with a present-day perspective as we travel south for a meaningful chapter centered first on the living story of the Wampanoag people, before continuing into Plymouth and its early-contact history.

We’ll begin at the Mashpee Wampanoag Museum, grounding the day in the voices and experiences of a living community rather than treating Indigenous history as something that exists only in the past. From there, we’ll continue to Plimoth Patuxet Museums, giving ourselves time to explore with context and curiosity instead of simply moving from one stop to the next.

After a real lunch pause in the Plymouth area, we’ll visit Mayflower II and spend some time along the Plymouth waterfront, including a brief stop at Plymouth Rock. It’s a simple landmark, but after everything we’ve explored earlier in the day, it may land a little differently.

Back in Boston, we’ll have dinner at The Haven in Jamaica Plain, followed by Boston Lights at Franklin Park Zoo — a colorful, lighter ending to a day filled with much deeper stories.

We’ll head to Salem early for a full day where maritime history, coastal New England, and the heavier story of the witch trials all live side by side. We’ll begin along the waterfront at Salem Maritime National Historic Site, taking in the historic wharves and views toward the Friendship of Salem at Derby Wharf before moving deeper into town.

Guests who want another layer can choose the House of the Seven Gables tour, one of Salem’s most recognizable literary and coastal landmarks. A guided walking tour will then help connect the streets, buildings, people, and events so the day feels like one unfolding story rather than a checklist of stops.

We’ll build in time for a lighter lunch, browsing Salem’s shops and seasonal pop-ups, and simply enjoying the October atmosphere. Later, we’ll slow down at the Salem Witch Trials Memorial, Old Burying Point Cemetery, and The Witch House, giving these places enough time to be experienced rather than rushed through.

If timing and hours allow, late afternoon leaves room for one more Salem layer — perhaps a little more waterfront time, shopping, or another museum stop. We’ll finish with a casual dinner at Boston Burger Company before heading back to Boston, a lighter ending after a day carrying some much heavier stories.

This morning, we step straight into Boston’s revolutionary story at the Boston Tea Party Ships & Museum, where the history feels immediate, interactive, and surprisingly personal. From there, we’ll begin our Freedom Trail walk through the downtown core, connecting places like Old South Meeting House, Old State House, and Granary Burying Ground as the story builds around us.

We’ll pause for lunch at Quincy Market, where everyone can choose what sounds best and enjoy a little time to browse before we continue. After lunch, we’ll move into the North End for Old North Church and the crypt tour, adding another layer to one of Boston’s most familiar revolutionary stories.

From there, we’ll continue into Charlestown for the USS Constitution, then finish at Bunker Hill Monument, bringing the day full circle with one of the defining chapters of the Revolution. Tonight, we’ll gather for dinner at the historic Union Oyster House — a classic Boston finish after a full day of walking through the story itself.

Today we trade Boston’s brick streets for the quieter landscapes of Lexington and Concord, where the Revolution shifted from ideas into action. We’ll begin at Lexington Green, then continue to Concord and the Old North Bridge, one of those places that feels familiar from books and photographs but lands differently when you’re actually standing there.

We’ll make time for a Concord museum stop to add context and bring the morning’s history into sharper focus, followed by a relaxed lunch nearby. In the afternoon, we’ll tour Orchard House, stepping into the world of Louisa May Alcott and the home so closely tied to her writing and legacy.

Before returning to Boston, we’ll slow down at Walden Pond for a reflective walk, choosing our distance based on energy and weather. It’s a quieter, more spacious ending to a week filled with big stories.

Tonight, we’ll gather for our final dinner at Alcove, ending the core trip with something warm, celebratory, and unhurried.

This morning is intentionally gentle, with breakfast at the hotel and time to pack, breathe, and take one last look at Boston before we head our separate ways. For guests heading home, airport transportation will be coordinated in advance based on departure times, so the morning can stay smooth and low-stress.

For guests concluding the core Boston trip, hotel checkout is at 11:00 AM, and our main expedition officially comes to a close this morning. Before we scatter back into regular life, we’ll take a moment to look back on everything we’ve walked through together — from living Wampanoag voices and Salem’s difficult history to the Freedom Trail, Concord, and Walden Pond — and let the full arc of the week land.

Guests continuing on the optional Cape Cod extension will head out with Christine early this morning for one more New England adventure, returning to our Boston-area hotel that evening for a final night.

OPTIONAL ADD-ON — This extension is not included in the core Boston trip price and must be purchased separately.

For those continuing the adventure, we’ll leave Boston early and head toward Cape Cod for one more full day of New England exploring. Our first stop is Sandwich, where we’ll spend some time along the coast before visiting the Sandwich Glass Museum and watching one of its live glassblowing demonstrations.

From there, we’ll follow portions of scenic Route 6A / Old King’s Highway, leaving room for historic villages, beautiful roadside stops, and whatever catches our attention along the way. After lunch, we’ll continue toward Cape Cod National Seashore, with time for Atlantic views, Nauset Light, and a chance to stretch our legs by the water.

Later in the afternoon, we’ll make our way to Chatham for its working waterfront, lighthouse views, local shops, and one last dose of classic Cape Cod charm. We’ll finish with a relaxed dinner before returning to our same Boston-area hotel for one final night — no packing up and changing hotels just for the extension.

OPTIONAL ADD-ON — This extension is not included in the core Boston trip price and must be purchased separately.

Our Cape Cod Extension wraps up this morning with breakfast at the hotel and a little time to pack, settle in, and enjoy one last easy morning before heading home.

Airport transportation is included and will be coordinated around departing flights so everyone knows the plan in advance. Hotel checkout is at 11:00 AM, with departure timing arranged as smoothly as possible around the group’s travel schedules.

It’s a simple ending after one more day of New England exploring — breakfast, goodbyes, and one final ride toward Boston Logan International Airport (BOS) before everyone heads home.