🧭 Past to Present Pathways: A Boston Urban Adventure (October 24 - October 30, 2026)

Boston is one of those places where the past does not sit politely behind glass. It lives in the street layout, the harbor wind, the brick under your feet - and in the way one story leads directly into the next. Past to Present Pathways is built as a chronological journey you can actually feel, beginning with the deeper roots of this land and moving forward through early contact, the Salem trials, the Revolution, and the quieter aftershocks that shaped American identity long after the fighting stopped. We will not be rushing past the “big” sites just to say we saw them. We will move with intention, with context, and with enough breathing room that the history can land.

This week is also designed to feel like Boston the way you hope it will - harbor views on the first night, an elevated skyline dinner, a full Salem day with time to shop and wander, and a Freedom Trail day that truly completes the loop all the way to Old North Church’s crypt tour, USS Constitution, and Bunker Hill. We will balance heavier moments with lighter ones, and we will end with the kind of places that naturally invite reflection - Orchard House and Walden Pond - before closing with departures that are smooth, supported, and simple. Come ready to walk, listen, laugh, and leave with more than photos - a story you can trace from beginning to end, and a sisterhood that makes it even better.

✨This trip is built for easy to moderate walking with flexible pacing - we will cover a lot of ground, but we will do it in a way that feels human. Some days are big story days with more time on our feet (Freedom Trail and Salem especially), and other moments are intentionally slower so the history can 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 - late October in Boston can shift quickly from crisp and sunny to breezy and damp. A light rain jacket, a small day bag, and a “city-walk” mindset will make everything feel easier and more enjoyable.  Christine will send packing suggestions in the months and weeks leading up to the trip.

What’s Included: All meals and snacks from first pickup to final drop-off, including hotel breakfasts (or elsewhere if we choose), lunches, and dinners, plus non-alcoholic drinks throughout the week (water, coffee/tea, and soft drinks). One choose-your-own lunch at Boston Public Market is on your own so everyone can eat 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 (timing may vary by arrival and departure), plus private group transportation throughout the week. Full itinerary planning, hosted guiding throughout the trip, and a shared photo gallery after we return home.

Not included: Airfare to and from Boston, and any lodging or meals outside the official trip dates (including anything before group pickup on October 24 or after checkout on October 30, unless you have arranged an early arrival add-on). Dinner on October 23 (early arrivals) and lunch on October 24 are on your own. Boston Public 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 holding space for connection and reflection while keeping the vibe 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, everything feels personal and flexible - we can linger when something lands, move efficiently when it matters, and stay connected as a group without getting lost in the crowd. Rooms are shared by default, with limited private upgrade options when available (final lodging assignments are based on the selected hotel room mix).

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 20% deposit is collected through WeTravel at checkout. This deposit holds your spot on this small-group experience.

• Deposit (20%) due upon booking (non-refundable after the grace period)

·         The remaining balance will be split into equal monthly payments, due on the 24th of each month, with final payment on August 24, 2026.

• Full terms will be included on your invoice, guest agreement, and waiver.

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 ensures you have time to fully review the experience and ask any questions before finalizing your commitment.

❗Cancellation Policy

• The 20% deposit is 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 is arrival and exhale—trip services begin with group arrivals into Boston Logan International Airport (BOS) (aiming for ~3:00 PM), with transfers coordinated around everyone’s flight times.

We’ll head to Residence Inn by Marriott Boston Harbor on Tudor Wharf to check in and settle in, and if rooms aren’t ready yet, Christine’s room becomes our “home base” for a quick reset.

Once we’ve landed, we’ll take an easy waterfront walk through the Charlestown Navy Yard, pausing at USS Constitution and continuing to Paul Revere Park for that first harbor-and-skyline moment. Dinner is a classic Boston welcome at Warren Tavern, cozy and historic in the best way.

We’ll end the night back at the hotel with a short Orientation Circle—just enough structure to feel grounded, without turning the week into a sprint.

After breakfast, we’ll step into the energy of Harvard Square, beginning with a relaxed walk through Harvard Yard—easy photo moments and that unmistakable campus atmosphere.

Late morning brings a grounding visit to the Harvard Peabody Museum of Archaeology & Ethnology, helping place Boston’s story inside a much longer human timeline.

Lunch stays simple in Harvard Square so we keep momentum without feeling rushed.

In the afternoon, we’ll slow down and take in the intimate beauty of the Isabella Stewart Gardner Museum, where the courtyard moment tends to stop people in their tracks.

Tonight is our “we might never be back” Boston moment: View Boston and dinner at Beacon Bistro, paired with sweeping city views as the skyline shifts from day to evening glow.

Today begins with a present-day lens, traveling south for a meaningful chapter that centers living Indigenous story before stepping into Plymouth’s early-contact sites.

We’ll start at the Mashpee Wampanoag Museum, holding space for the truth that these stories are still lived—not just remembered.

From there we continue to Plimoth Patuxet Museums, moving with context and intention rather than rushing from stop to stop.

After a real lunch pause in the Plymouth area, we’ll visit Mayflower II and take a brief waterfront moment where even quick landmarks land differently after the morning’s depth.

Back in Boston, dinner is at The Haven in Jamaica Plain, followed by an evening at Boston Lights at Franklin Park Zoo—a little magical, and a welcome exhale after a story-heavy day.

We’ll head to Salem early for a full day where waterfront beauty and heavier history live side by side.

We begin at Salem Maritime National Historic Site, taking in sea air, historic wharves, and harbor views—including a look toward the Friendship of Salem from Derby Wharf.

Those who want the extra layer can join the House of the Seven Gables tour—classic New England texture that adds depth to the day. A guided walking tour helps stitch Salem together into a story you can actually follow, not just a list of stops.

We’ll build in time for shops and seasonal October energy, then spend meaningful time at the Salem Witch Trials Memorial, Old Burying Point Cemetery, and The Witch House (with enough time so it doesn’t feel like a rushed photo stop).

Dinner is a fun exhale at Boston Burger Company before we return to Boston.

This morning we step straight into the revolutionary heartbeat at the Boston Tea Party Ships & Museum, where the story feels surprisingly hands-on and immediate.

Then we begin walking the Freedom Trail, taking time at core downtown sites like Old South Meeting House, Old State House, and Granary Burying Ground so the history actually lands. Lunch is at Boston Public Market—this is your choose-your-own moment, with time to wander and pick what sounds best.

After lunch we head into the North End for Old North Church and the crypt tour, adding a deeper layer that makes the day feel real, not just famous.

We’ll continue into Charlestown for USS Constitution, then finish with the climb to Bunker Hill Monument, closing the loop in the most satisfying way.

Dinner tonight is at the historic Union Oyster House—a classic Boston finish to a big, iconic day.

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 hits differently when you’re standing there yourself.

We’ll add a museum stop for context, then take lunch nearby before the afternoon turns more personal and literary.

We’ll tour Orchard House, stepping into the world of Louisa May Alcott and the home that shaped her legacy.

Before returning to Boston, we’ll slow down at Walden Pond for a reflective walk—distance chosen by energy and weather, with plenty of room to breathe.

Tonight we gather for our final dinner at Alcove, warm and celebratory without being rushed.

This morning is simple and gentle—breakfast at the hotel, time to pack, and one last look at Boston Harbor before we scatter back into regular life.

Airport transfers are coordinated based on flight times, with early transport available. For later flights, the JFK Presidential Library and Museum is a beautiful optional final chapter if timing allows.

Hotel checkout is 11:00 AM, and trip services conclude at checkout, with transfers available prior to 12:00 PM (unavailable after).

Before we go, we’ll take a final moment to look back on the full arc we walked together—from living Wampanoag voices to Salem’s lessons, from the Freedom Trail to Walden—and let it land.