Portugal
— IN GOOD COMPANY
The Next Chapter Retreat
A Twelve-Day Walking Journey Through Lisbon and Madeira
September 28 - October 9, 2026
An intentionally small group of women
The Moment Many Women Recognize
Many of us spent decades succeeding
in systems that were not built for us.
Now we have the opportunity
to define the next chapter ourselves.
We built careers.
We built families.
We carried responsibilities at work and at home.
And now, something begins to shift.
For the first time in many years, the question becomes:
What do I want this next chapter of life to be?
CLARITY
A chance to step back from daily demands and hear yourself think again.
FREEDOM
A stage of life where expectations loosen and new choices emerge.
CONNECTION
Time with thoughtful women navigating many of the same questions.
This stage of life brings new questions.
This stage of life brings new questions.
Children grow up.
Careers evolve.
Our bodies change.
Our priorities become clearer.
For many women, it is the first time in decades that space opens to ask:
What do I want more of now?
Clarity matters.
Connection is what stays.
This retreat was created to offer something more enduring than a single journey alone.
We believe meaningful connection develops gradually — through time spent walking side by side, through shared meals, through conversations that unfold naturally.
Not through performance or pressure, but through presence.
The structure of this journey is intentional.
Two beautiful hotel bases — one along the Lisbon coast and one on the island of Madeira — allow the experience to unfold at a thoughtful pace. Each day is designed to balance walking, discovery, rest, and conversation.
The journey begins before we arrive in Portugal, with opportunities to connect as a group and begin getting to know one another.
And it continues after we return home, as the relationships formed during the journey carry forward in ways that feel natural and meaningful.
Travel often brings remarkable encounters that fade once we return home.
We wanted to create something different.
Not simply a journey through beautiful places —
but a community that continues long after the journey ends.
Why We Created This Journey
Twelve Days. Fully Lived.
Long enough to settle into the rhythm of Portugal — and long enough for connection to deepen and clarity to emerge.
01
Arrival & Closing Days
Time to arrive fully.
Time to settle in.
Time to depart unhurried.
The journey is intentionally bookended with space — to land gently, to connect as a group, and to close the experience with clarity.
Private transfers welcome you on arrival and return you to the airport at the end, allowing the journey to begin and conclude with ease.
02
7 Days of Guided Walking
Seven days of beautiful walking unfold across two remarkable landscapes.
Along the Lisbon coast, paths wind through ocean air, quiet villages, and centuries of history.
Later, on the island of Madeira, dramatic cliffs, forested levadas, and sweeping Atlantic views create a different rhythm of discovery.
Private transfers and thoughtfully selected routes ensure your energy is spent on the experience — not the logistics.
03
Shared Meals & Cultural Experiences
Shared meals anchor the rhythm of the journey.
Some evenings unfold at our hotel base — relaxed gatherings shaped by seasonal ingredients, regional wines, and the pleasure of lingering at the table.
At times, a private chef prepares dinner, offering a deeper taste of the traditions and ingredients of the region. On other evenings, we venture out to local restaurants where the atmosphere of Portugal reveals itself slowly.
Along the way, cultural encounters are thoughtfully woven into the days — intimate moments with local makers, historians, and guides who bring the places we walk through to life.
04
Two Eco-Luxury Hotel Bases
We stay in two carefully selected properties — one near the Lisbon coast and one on the island of Madeira.
These may take the form of a farm stay, a shared villa, or a boutique eco-luxury property — places chosen for their character, comfort, and connection to the landscape.
Returning each evening to the same base allows the experience to unfold without constant packing or movement.
Comfort, stability, and restoration are woven into the journey.
05
Thoughtful Support
Private transfers move us seamlessly between locations and walking routes, allowing the focus to remain on the experience itself.
Local guides share the history, culture, and stories of the places we visit, grounding the journey in the living character of Portugal.
A short flight brings us to the island of Madeira, where the landscape shifts dramatically and the second half of the journey begins.
Behind the scenes, an experienced in-country travel partner oversees the logistics of each day.
Your retreat host holds the space for connection — offering thoughtful guidance so conversations deepen naturally.
Everything is quietly tended to.
The Rhythm of The Journey
Morning & Walking
Mornings begin unhurried.
Breakfast together. A considered route. A steady departure.
Early in the journey, local guides introduce the history and character of Portugal, offering context that deepens the landscapes and places we walk through in the days that follow.
Some days follow the Lisbon coast — ocean air, quiet villages, and paths shaped by centuries of passage.
Later, the landscape shifts to Madeira, where dramatic cliffs, forested levadas, and sweeping Atlantic views invite a different kind of discovery.
There is space to walk beside someone.
And space to walk alone.
The Day Unfolds
Along the way, thoughtfully chosen cultural encounters are woven into the days — moments with local makers, historians, and hosts who share the living culture of Portugal.
Each experience honours place, supports local communities, and reflects the spirit of the region.
Midday brings pause — sometimes a shared table, other days a simple grazing stop before continuing on.
The Evenings
Evenings return you to the comfort of your hotel base.
Some nights gather around a table prepared by a private chef.
Other evenings unfold in local restaurants where conversation stretches and the atmosphere of Portugal reveals itself slowly.
Dinners linger. Laughter moves easily around the table.
The Change
The experience is thoughtfully supported — never over-directed.
Logistics are handled seamlessly. Dialogue is gently guided.
The days feel spacious, yet intentional.
And over twelve days, something steadies.
You listen differently.
You think more clearly.
You return changed — quietly, but unmistakably.
And somewhere along the way strangers become friends.
Who This Journey Is For
This journey is designed for women who have built full lives — and are now choosing more intentionally how they spend their time and energy.
You bring experience.
Perspective.
Stories earned through living.
You are no longer interested in collecting experiences for their own sake. You are drawn to depth — to conversations that matter, to places that stay with you, to people who expand your thinking.
A thoughtfully assembled group matters to you. You value being in the company of curious, capable women — women who bring something distinctive, and who are equally interested in what others bring.
You are drawn to walking not as a challenge, but as a rhythm. A way of moving through a place slowly enough for reflection to emerge and connection to form naturally.
You appreciate thoughtful design and expert curation. You understand that when logistics are handled well, your energy can be directed toward experience, conversation, and discovery.
You are open. Engaged. Willing to participate — not simply observe from the edges.
There will be laughter — because when thoughtful women gather without hurry, ease and humour tend to follow.
This journey is for women who want more than a trip.
It is for those who want to be part of a circle that forms during the journey and continues, in its own way, long after the days in Portugal have ended.
In the Right Hands
This experience is designed to feel effortless — because it is held by women who have guided journeys like this many times before.
From logistics on the ground to the quieter work of shaping connection, every element is supported with professionalism, discernment, and care.
Jane Iannacone
Retreat Host
Jane is the founder of Jigsaw Performance, a boutique advisory firm working with entrepreneurs and leadership teams across Canada.
She has hosted numerous retreats across British Columbia and the Pacific Northwest, specializing in small, thoughtfully assembled groups.
Her work centres on thoughtful conversation, genuine connection, and the formation of meaningful community among capable women.
Jane’s approach is light-touch and intentional.
The structure is quiet.
The conversations are real.
The atmosphere is steady, spacious, and unforced.
Lystra Germaine Sam
Founder, Qmooniti Travel & Lifestyle
In-Country Travel Lead
Based in Vancouver and traveling with us in Portugal, Lystra oversees the journey on the ground — coordinating accommodations, routes, transfers, and local hosts with calm precision.
She brings years of experience designing travel that feels immersive yet seamless, allowing guests to relax fully into the experience.
Through Qmooniti, she curates culturally rooted travel grounded in reciprocity and respect — ensuring each encounter honours place, supports the local economy, and reflects the living culture of Portugal.
Her presence ensures the journey moves smoothly, with contingency built in and every detail thoughtfully considered..
Together
Together, we bring complementary experience in leadership, community-building, and thoughtfully curated travel.
Jane brings decades of experience guiding entrepreneurs and leadership groups through conversations that create clarity, trust, and meaningful connection.
Lystra brings deep expertise designing and leading immersive travel experiences — creating journeys that feel seamless, culturally rooted, and beautifully held from beginning to end.
Together, we have guided many retreats and understand how powerful shared journeys can be when they are thoughtfully designed.
Our role is to hold the structure of the journey — so you are free to experience it.
So that you can simply arrive…
and be in it.
This is not a spontaneous trip.
There comes a point when stepping away is not indulgence —
but wisdom.
A chance to see clearly again.
To walk, to think, to connect.
And to return to your life with renewed clarity.
——————
Portugal — In Good Company
PORTUAL • LISBON TO MADEIRA
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Twelve Days. Fully Lived
A deeply curated twelve-day journey through Portugal — thoughtfully designed so you can simply arrive, walk, connect, and be fully present.
An intimate experience, intentionally limited to a small circle of women.
INVESTMENT
Because this experience is intentionally limited to a small group, full investment details are shared privately with those who request additional information.
This retreat is currently being shared with a small invitation circle before opening more broadly.
If you feel drawn to this journey, we invite you to request details and begin the conversation.
Final dates and accommodations will be confirmed with those who request additional details.
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What is Included
Twelve-day fully curated journey
Seven guided walking days at a considered pace
Accommodations in two distinctive Portugal bases — a countryside retreat and a coastal island stay
Thoughtfully prepared meals throughout the journey — including private chef dinners and exceptional local restaurants
Carefully curated, locally rooted cultural encounters
Experienced in-country travel leadership
Retreat host and lightly guided dialogue
Flights to/from Madeira and Lisbon
Private transfers and route support
What is Not Included
Flight to/from Portugal
Travel insurance (recommended)
Personal purchases and incidentals
PAYMENT
Once your participation is confirmed, a deposit will secure your place.
The remaining balance will be payable prior to departure. Payment plans will be available for those who prefer to spread the investment over several months.
If you have questions, you're welcome to reach out directly:
jane@jigsaw-performance.com