A BEAUTIFUL PAUSE
In Good Company
A Beautiful Pause
Step away.
Walk together.
Return renewed.
A thoughtfully curated walking journey in Portugal for women who feel ready for something more — more space, more depth, and more meaningful connection with others and themselves.
Across twelve days and two remarkable regions — the Lisbon coast and the island of Madeira — we walk, share conversation, and experience Portugal at a pace that allows perspective to emerge.
You will return home clearer, grounded, and restored.
October 2026 • Early applications encouraged
Participation is intentionally limited to support meaningful connection and shared experience.
When You Choose Something Different
There comes a point when you choose something deliberately — not because you're overwhelmed, but because you value how you spend your time now.
You’ve built a full life. You carry responsibility with steadiness and care.
And now, perhaps, you feel ready to step away for a time.
This journey is a thoughtfully curated walking experience in Portugal, created for women who appreciate shared discovery, unhurried conversation, and exceptional attention to detail.
The days are intentionally designed.
Two beautiful hotel bases anchor the experience — one along the Lisbon coast and one on the island of Madeira — allowing you to settle into a place rather than move constantly. Each walking route is selected for both scenery and flow.
An experienced in-country host oversees each detail so you can remain fully present.
Nothing is rushed. Nothing is overlooked.
You are free to arrive fully and be immersed in the rhythm of the days.
To walk with intention.
To connect without agenda.
To return to your life clearer.
What makes that possible is how the journey is designed.
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
The Beginning of the Day
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 experience of the landscapes and places we walk through in the days that follow.
The Walking
Some days unfold along the Lisbon coast — ocean air, quiet villages, and paths shaped by centuries of passage.
Later, the landscape shifts to the island of 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, carefully curated cultural encounters are woven into the days — intimate moments with local makers, historians, and hosts who share the living culture of Portugal.
Nothing performative.
Nothing extractive.
Each experience chosen to honour place, support the local communities, and reflect the spirit of the region.
Midday brings pause — sometimes a long table and a shared meal, other days a simple grazing stop along the route before continuing on.
The Evenings
Evenings return you to the comfort of your hotel base — familiarity anchoring the rhythm of the journey.
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.
Stories unfold.
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 clarity, trust, and the formation of meaningful community among capable women.
Jane’s approach is light-touch and intentional — offering enough structure for the group to settle while ensuring the experience never feels managed.
Conversations unfold naturally.
The tone remains steady, spacious, and real.
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.
A Beautiful Pause
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.
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.
$XX,XXX
CAD
Per person.
What is Included
Twelve-day fully curated Camino 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
Private transfers and route support
What is Not Included
Flight to/from Portugal.
Travel insurance (recommended).
Places are limited in order to preserve the depth and quality of the experience.
Payment
A deposit secures your place once your participation is confirmed.
The remaining balance is payable prior to departure.
Payment plans are available.
The group is intentionally limited to preserve the quality of the experience.
Questions? Email Jane @Jigsaw-Performance.com