Portugal · Early October 2026

This is
your time.

The life you designed in your thirties doesn't quite fit anymore. Not because something went wrong. Because something went right.

Eight days in Portugal — with the right women beside you — to design what comes next.

Send Me the Details

Small group · Good wine · One departure

Something is changing

Children growing up.
Careers evolving or no longer fitting in the same way.
Work that once energized you, now feeling like it needs to change.
Parents needing more.

And with that, a different kind of question emerges:

What do I actually want now?

Not what makes sense to the people around you. Not what looks right from the outside. Not the next obvious step.

What do I want this next chapter to feel like — and what would it look like if I actually designed it?

Not by default — but by design.

And the women you'll walk with are asking the same questions.

That's what makes this different — you're not figuring it out alone.

And this — this is the most interesting chapter yet.

On your own terms

You've given everything to every chapter so far. This one is yours.

What carried you here won't necessarily carry you forward. That voice telling you to wait — to let this moment pass, to circle back when things settle — it isn't protecting you. It's the same voice that's always asked you to wait your turn.

You don't have to know exactly what you want yet. You just have to be curious enough to find out.

Why walking

There's something about walking that loosens things.

When you move through a place at a human pace — along a coastal path, through a sun-warmed vineyard, into a village where time feels different — thoughts and ideas surface more honestly than they do at a desk or in a meeting room.

Walking is one of the oldest forms of healing. Natural movement has a way of flushing the body and the mind — releasing what's been held, making room for something quieter to come through.

And sometimes it isn't about figuring something out. Sometimes it's simply about allowing yourself a moment to be — to let go, in the company of women who get it.

This is where clarity begins.

Why this retreat exists

Why I created this

Because there comes a point when doing the same isn't enough anymore — when life shifts and you find yourself asking who am I now, and what matters to me at this stage of my life.

You can be surrounded by people, showing up for everyone else — and still feel a little disconnected from what you want.

Clarity doesn't come from pushing harder. It comes when you give yourself time and space — and when you're in the company of women asking the same questions.

That's what makes this different — you're not figuring it out on your own.

Not a fixed plan.
But the beginning of what's next.

A note from Jane

The idea had never once occurred to me — until someone showed me it was possible.

Taking a leap of faith is scary. In 2010, I was struggling with the demands of my career and trying to figure out summer camps for my boys. I wanted more flexibility, more time with them — and somewhere underneath all of it, I knew something had to change.

But wanting something different and believing you can have it are two very different things.

What shifted wasn't a plan. It was permission. I gave myself permission to want something different — and once I did, things began to move. We bought a cabin on Lake Okanagan. I left my employee job and became a contractor.

I have never looked back. It was the best thing I ever did for my family — and for myself.

None of it would have happened if someone hadn't shown me, quietly and without fanfare, that a different choice was simply an option.

— Jane Iannacone Retreat Founder

Send me the details

Leave your email and I'll send you everything you need to decide if this is for you — the full experience, the dates, the investment, and a few things I don't share anywhere else.

The team

This retreat is a collaboration between two people who each bring something essential — one designs what happens inside, the other designs everything that moves.

Jane Iannacone

Retreat Founder
Program Director

For more than twenty years, Jane has helped business owners and leadership teams step back, ask better questions, and find clarity when navigating change. Since 2014 she has designed and led retreats for women entrepreneurs and leadership teams — and she knows how to create the kind of room where people surprise themselves.

Over the course of the journey, Jane creates moments of reflection — a question shared over breakfast, a thought offered between landscapes. Nothing formal. Nothing required. Just the right question at the right moment.

Lystra Germaine Sam

Founder, Qmooniti Travel
In-Country Lead

Based in Vancouver and travelling with us in Portugal, Lystra designs and leads the entire travel experience — accommodations, routes, transfers, and local hosts, coordinated with calm precision.

Through Qmooniti, she curates travel grounded in cultural reciprocity — ensuring every encounter honours place, supports the local economy, and reflects Portugal as it actually lives. She isn't managing this from a distance. She travels with you.

You bring yourself — your appetite, and an openness to what unfolds. We take care of everything else.

So you can simply be part of it — with the right people around you.

This is not a trip you plan. It's one you surrender to.

What makes this different

What eight days looks like

Each day carries a simple theme — a lens drawn from the world of strategic thinking, shared over breakfast and carried into the walk. Nothing to complete. Nothing to get right. None of it requires anything of you except showing up. Just a question worth sitting with, and a conversation worth returning to over dinner.

Morning

Yours to shape

The gym, a yoga session, quiet meditation, or a long coffee with the view. Your morning rituals are honoured here. The day's lens — a simple idea to carry into the hours ahead — is shared over breakfast when you're ready.

Day

Walking somewhere worth going

Coastal paths with the Atlantic below. Vineyards at harvest. Villages where time moves differently. Five days of guided walks through landscapes that reward a slower pace — woven with cultural encounters, local makers, and guides who bring each place to life.

Evening

The kind you don't want to end

Fresh, seasonal food. Excellent local wine. Sometimes a private chef; sometimes a restaurant where Portugal reveals itself slowly. And always: good conversation, real laughter, and the unhurried ease of being somewhere with exactly the right people. Turns out, when no one needs anything from us, we're very good company.

Outdoor dining table set for the group with mountain views

It might be exactly what you need right now.

From women who've been in the room

You don't need to arrive with answers. Just a willingness to be part of it.

On the Methodology

Jane asks really, really good questions. It really made me dig deep and think about a lot of things — things that hadn't even crossed my mind, or that I hadn't been putting enough emphasis on. I found it really useful.

Lorena K.

Retreat participant

"The sense of community was the most powerful part for me. Being with other women who understood what I was experiencing made everything feel less overwhelming, and I left feeling more confident and clearer about what comes next."

Nicole N.

Retreat participant

"Being part of this experience reminded me I wasn't alone. The connection with other women, the perspective I gained, and the confidence I left with made it deeply meaningful."

Nicole P.

Retreat participant

Send Me the Details

Before you ask

Your questions, answered.

Here are the things most women want to know before they take the next step.

Is this retreat right for me?

The women who come on this retreat have built full lives. They're thoughtful, curious, and genuinely good company — drawn to depth, to conversations that go somewhere, and to people who expand their thinking.

They show up open and willing — quirks, contradictions, and all. Fair warning: there will be laughter. The unguarded, slightly-surprised-by-yourself kind. And they tend to find, somewhere over the eight days, that they're more themselves than they've been in a long time.

If any of that sounds like you — it probably is.

Will I have my own room?

Most women will have their own room. If you're attending with a friend and would prefer to share, a small number of double-occupancy rooms are available, with a cost saving. If you have a room preference, we recommend joining early. Either way, your accommodation is fully included.

Can I come on my own?

Most women do. The pre-trip gathering — held before departure — means you'll already know the women you're travelling with before you land in Lisbon. You arrive as part of a group, not as a stranger.

And the connection doesn't end in Portugal. Women who walk, think, and share like this together don't easily lose each other — after the retreat, the group stays connected in a shared space.

Is it just walking, or are there other experiences?

This isn't for women who want a tour. It's for those who want an experience — the kind where, when you try to explain it afterwards, you find yourself smiling, reaching for the moments that moved you. A conversation that cracked something open. A laugh you didn't see coming. The wide-eyed feeling of finally figuring out something that matters.

Walking is the spine of the experience — but the days are shaped by much more than that. We begin in Lisbon with a guided exploration of the city: its history, its neighbourhoods, its particular way of moving through time. Along the way, cultural encounters are woven into each day — with local makers, historians, and guides who bring the places we move through to life. Some evenings unfold over a private chef dinner featuring regional ingredients; others take us to local restaurants where Portugal reveals itself slowly.

Every experience is chosen to be immersive rather than touristic — encounters that leave you with a felt sense of Portugal, not just a photograph of it.

What kind of place will we be staying?

Authentically Portuguese and eco-luxe — a property chosen for character and soul as much as beauty. Sweeping views, beautiful spaces, and the kind of considered comfort that means you never want to leave. Somewhere you can truly settle in.

We are finalising the property now, and it will be worth the wait. Full property details shared first with everyone on our list.

Selected through Lystra's Qmooniti lens — not just for beauty, but for the way it connects you to Portugal as it actually lives. Character, comfort, and a sense that this place was chosen specifically for you.

How much walking is involved? Do I need to be fit?

Five days include guided walks. These are not performance walks — the pace is unhurried and routes are chosen for atmosphere and landscape, not difficulty. If a particular day doesn't feel right for you, there's no obligation to join every walk. This experience is shaped around you, not the other way around.

How many women will be in the group?

The group is intentionally small — 15 to 20 women — enough to feel like a genuine circle, small enough that everyone knows everyone by the end of day one. It's the number where conversations go somewhere they can't in a larger group.

The group size isn't a capacity limit — it's a design choice.

What are the dates?

The retreat runs from the end of September into the first week of October 2026. The group will be home by October 8th at the latest — in plenty of time for Canadian Thanksgiving weekend.

Exact dates are confirmed and shared with everyone on our list once the itinerary is locked. If you're thinking about flights, October 8th is your planning anchor.

Do I need to book my own flights?

You're welcome to book your own flights, or have them arranged for you. Lystra can coordinate flights on your behalf, with access to industry tools and fare options not typically available to individual travellers. Where possible, she can also align flights so you're travelling with others in the group.

We'll share recommended timing once the retreat is confirmed, so you can book with confidence.

Through Qmooniti Travel, Lystra can also arrange extended stay options for those who'd like to spend more time in Portugal before or after the retreat — whether that's a few extra days in Lisbon, a coastal escape, or something further afield. Just let us know.

What if I need to cancel?

We know life happens. Here's how we handle it:

Cancel before June 1, 2026: full refund minus a $500 administration fee. Cancel June 1–August 1, 2026: 50% refund. Cancel after August 1, 2026: no refund — however, we will make every effort to transfer your spot to another woman, and if your spot is filled, you receive a full refund minus the $500 fee.

If we cancel the retreat: full refund within 14 days, no exceptions.

Travel insurance with trip cancellation and medical coverage is required to attend. We strongly recommend purchasing your policy within 14 days of paying your deposit, and suggest looking for a policy that includes Cancel For Any Reason (CFAR) coverage for maximum flexibility.

What is the investment?

This is a fully curated, all-inclusive experience — private rooms, chef-prepared meals, local expert guides, and private transfers throughout, with Lystra on the ground with you every step of the way. Airfare not included.

Leave your email and pricing comes to you first — before it's shared anywhere else.

Full investment details will be shared as soon as they're confirmed — and you'll receive them the moment they are.

The right place, at the right moment in your life.

Where eight days begins · Lisbon · Portugal · October 2026

What becomes possible

Clarity. Energy. Permission.

Three things that quietly return when women finally give themselves space to pause.

Clarity

Hearing your own thoughts again

The kind that comes when you step outside the noise. What matters becomes simpler — and often, more obvious than you expected.

Energy

Not from doing more

From being in a place that restores something in you — and in the company of women who expand your thinking. The kind of energy that comes from feeling lighter, freer, and fully present.

Permission

To want something for yourself

To choose what brings meaning, satisfaction, and joy — without needing to justify it to anyone, including yourself.

And somewhere in that space,
you begin to remember what feels like you.

One departure · Portugal · October 2026

You've been waiting for the right time. This is it.

More than a trip — something that happens when the right people come together.

Leave your email and I'll send you everything you need to decide if this is for you. No obligation. No pressure.

This is
your time.

Something is changing

Not a tour. Not a workshop. Something better.

You've given everything to every chapter so far. This one is yours.

Why walking

Why I created this