In Good Company
A walking journey in Portugal
Clarity.
Connection.
Freedom.
You’ve spent a lifetime building.
Working. Carrying. Achieving.
Moving forward—often against the current.
And then, quietly, something begins to shift.
Not because anything is wrong.
But because you’ve changed.
This is a chance to step back.
To walk.
To reflect.
And to reconnect with what matters now.
Does this sound like you?
You’ve spent years building a life that works.
You’re capable. Independent.
Used to figuring things out on your own.
You’ve become very good at showing up for others—
less practiced at making space for yourself.
And lately, something feels different.
The pace no longer fits in the same way
Some relationships have shifted or faded
What once felt important doesn’t carry the same weight
You’re asking quieter, more personal questions about what comes next
Not because anything is wrong.
But because you’ve changed.
Why We Created This Journey
There comes a point when stepping away is no longer a luxury—
it becomes necessary.
Not to escape life,
but to see it more clearly.
We created this journey for women who feel that shift.
Women who have spent years building, leading, supporting—
and are now ready to ask a different question:
What do I want, now?
And what would it take to create a life that feels truly good to live?
Not just successful.
But meaningful, connected, and alive.
And while that work can be done alone,
there is something far more powerful about doing it together.
Why Portugal
Portugal is a country that understands transition.
Over time, something shifted.
The pace slowed.
The focus turned inward.
What once defined success
no longer held in the same way.
Today, there is a different rhythm here.
Slower.
More grounded.
More present.
In many ways, it mirrors a transition
many women experience.
A life once shaped by striving and responsibility—
now opening into something more intentional.
More personal.
More your own.
Portugal doesn’t rush you forward.
It invites you to slow down—
and experience things differently.
Why Walking
Walking creates a different kind of space.
We’ve built lives that remove friction.
Everything is faster, easier, more efficient.
But many of the most meaningful moments
don’t come from ease.
They come from slowing down.
From having the time to notice.
Walking brings that back.
You are away from your routines.
Away from constant input.
There is just enough movement
to settle the mind—
and just enough quiet
for something deeper to surface.
Thoughts begin to organize.
Questions become clearer.
What matters has a way of rising.
Not because walking changes everything—
but because it creates the conditions
for you to see more clearly.
CLARITY
Seeing your life as it is—and as it could be
There comes a point when adding more
doesn’t make the picture more beautiful.
It just makes it harder to see.
This chapter may not be about doing more.
It may be about noticing what no longer fits.
What you’ve outgrown.
What no longer feels like yours to carry.
What is ready to be set down.
Clarity comes from seeing clearly—
and having the space to do it.
CONNECTION
Being in the company of women
who understand this moment
Many of us are used to figuring things out on our own.
But we do not fully know ourselves in isolation.
There is something powerful about being with women
who are asking similar questions,
navigating similar shifts,
and open to honest conversation about what comes next.
We see ourselves differently
when we are mirrored well.
And in that reflection,
something begins to settle.
FREEDOM
Moving forward with intention —
not obligation
Freedom doesn’t always come from changing everything.
Sometimes it comes from seeing your life differently.
From loosening what no longer fits.
From letting go of what was never yours to carry.
From choosing what feels right now.
Not the freedom of escape.
The freedom of alignment.
The Journey Includes
A 12-day, thoughtfully curated experience across two regions of Portugal—designed to balance movement, reflection, and meaningful connection.
Structure of the Journey
12 days in Portugal
Two regions
Lisbon & the Coast, and Madeira
Seven guided walking days
A mix of shorter and longer routes
Two hotel bases
Settle in—no constant packing or moving
This is not a tour.
It’s a curated experience designed to create the conditions for clarity, connection, and forward movement.
Walking Experience
Guided walks designed for enjoyment, not endurance
A mix of coastal paths, historic routes, and natural landscapes
Time and flexibility to move at your own pace
Support throughout, with space for both conversation and quiet
Connection & Experience
Shared meals in beautiful, locally rooted settings
Natural, unstructured conversation throughout the journey
A small, intentionally curated group of women
Time for both connection and personal space
Before & After the Journey
A private group gathering prior to departure
Ongoing connection with the group after returning home
This Journey is for You if…
You have built a full life—
and are now choosing more intentionally how you spend your time and energy.
You are capable. Thoughtful.
Used to figuring things out on your own.
You’ve spent years showing up for others—
and are ready to create more space for yourself.
You are no longer drawn to 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 are equally interested in what others bring.
You are drawn to walking not as a challenge,
but as a rhythm.
A way of moving slowly enough
for reflection to emerge
and connection to form naturally.
You appreciate when things are thoughtfully designed and well held—
so your energy can be directed toward experience,
conversation,
and discovery.
You are open. Engaged.
Willing to participate—
not simply observe from the edges.
You’re not looking for more to do.
You’re looking for a different way to move forward.
This is not for everyone.
And that is part of what makes it meaningful.
In Thoughtful Hands
This experience is being created with care by women who understand both the practical side of retreat design and the deeper purpose behind gathering this way.
The journey will be beautifully held,
thoughtfully paced,
and designed to create both structure and space.
So that you can arrive, settle in,
and be present for what this experience is really here to offer.
Jane Iannacone
Jigsaw Performance
Retreat Host
Jane works closely with entrepreneurs and leadership teams, helping them navigate growth, change, and what comes next.
Her approach to this journey is grounded in thoughtful conversation, real connection, and creating space for what matters to emerge.
Lystra Germaine Sam
Qmooniti Travel & Lifestyle
In-Country Travel Lead
Lystra designs and leads thoughtfully curated travel experiences around the world.
Her work ensures that every detail is seamlessly handled—so the experience feels natural, unforced, and deeply considered.
A chance to return differently
Not to escape your life.
To return to it with more clarity,
more connection,
and a deeper sense of freedom in how you move forward.
This is not a spontaneous trip.
It is a considered choice—
to step back,
to pay attention,
and to engage with what this next phase of life is asking of you.
The group will be intentionally small.
Details will be shared with women who feel genuinely drawn to this experience.
PORTUGAL • LISBON TO MADEIRA
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
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?
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.
And somewhere along the way strangers become friends.
If you have questions, you're welcome to reach out directly:
jane@jigsaw-performance.com