Walking. Talking. Portugal. · October 1–8, 2026

The next chapter
is yours to design.

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

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Before you read further

Are your children becoming more independent — and wondering what comes next for you?

Have you caught yourself asking what you actually want for the next ten years?

Do you want concentrated time that's entirely your own — and the right women around you?

Are you ready to give yourself the space to find out?

If any of that sounds like you, keep reading.

Something is changing

Children growing up.
Careers evolving.
More space than there used to be.

And with that, a different kind of question emerges:

What do I actually want now?

Not what makes sense to the people around me.
Not what looks right from the outside.

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

That's the question we'll explore together.

Through beautiful places.

Unhurried conversations.

And the company of women who understand exactly why you're here.

Not by default — but by design.

And from where I'm standing, this might be the most interesting chapter yet.

Women from a previous retreat toasting together at golden hour

Sisterhood

The women you'll walk with

And now they're making space to ask a different question:

What do I want next?

Not because something is wrong.

Because this chapter matters too.

The women you'll walk with aren't looking for someone to tell them the answer. They're creating the space to discover it for themselves.

You're not figuring it out alone.

That's what makes this different.

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

Cliff paths where the Atlantic breaks white far below. October vineyard rows still heavy with fruit, the air carrying something warm and almost sweet. Stone villages where the fountain in the square has been running for five hundred years. Five days of guided walks that do something to you — woven with cultural encounters, local makers, and guides who open the places most visitors drive past.

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.

Dinner table set on the balcony at Canto do Sol, mountains beyond

It might be exactly what you need right now.

A note from Lystra

A moss-covered stream in the forest near Soajo, Northern Portugal

The experiences I'm designing for this week aren't activities. They're encounters.

Regenerative farming sessions that bring you into relationship with the medicine the land has to offer — and how it connects to your own wisdom and your current desire for a more restorative, rooted life.

Local crafts and storytelling that invite you into a more true and generous history, grounded in the care that women have always passed between generations.

Daily movement practices to slow-start your mornings and softly wrap your evenings. Sunset water rituals. Unexpected cultural encounters chosen for what they give you, not what they show you.

Every experience is an act of reciprocity — between you and this place, between this group of women and the people who call Portugal home. I'll be with you for all of it.

— Lystra

The fine print, made simple

What's included

Dinner at the retreat — food by Kat & Mel

Included

— Seven nights at Canto do Sol — a family-owned eco-lodge where valley views stretch from your bedroom window, the natural pool catches the afternoon light, and evenings smell of whatever is growing in the garden.
— All meals — unhurried breakfasts with local bread, cheese, and fruit. Long lunches outdoors. Dinners that begin at dusk and end when the conversation does — sometimes a private chef cooking regional seafood in the open kitchen, sometimes a local restaurant where the wine is poured generously and the bread arrives warm.
— Two massages — the kind that work through tension you didn't know you were carrying, in a quiet room that actually earns its silence. Scheduled when they suit you.
— Yoga and pilates — morning sessions that ease you into the day before the walk, and evening practices that bring it gently to a close. On the terrace when the light is right.
— Five guided walking days — cliff paths above the Atlantic, ancient pilgrimage routes through stone villages, October vineyards still heavy with fruit. Each route chosen by Lystra for what it gives you, not what it checks off.
— Cultural encounters curated by Qmooniti — a morning with a local maker whose craft has been passed between hands for generations, a guide who opens places most visitors drive past, a farmer who knows what this land has always known.
— Daily retreat programming — a question, offered over breakfast, to carry into the walk. Not an assignment. A lens. Drawn from twenty years of helping people think clearly about what matters most to them.
— All group transportation — you never have to think about getting anywhere. The road between places is often where the best conversations start.
— Pre-retreat virtual gathering — before you fly, you meet the women you'll be travelling with. By the time you land in Porto, you're meeting people you've been looking forward to seeing.
— Personalized travel support from Qmooniti — flights, transfers, and extended stay options arranged for you, with access to fares and connections most travellers can't reach independently.

Not included

— Airfare to and from Portugal
— Travel insurance (required)
— Airport transfers to and from the retreat location
— Personal purchases
— Alcohol beyond what's included in meals and hosted experiences
— Additional accommodation before or after the retreat
— Optional activities you arrange independently outside the retreat program

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

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

This retreat is built around walking. Not as exercise — as a way of moving through ideas. Northern Portugal is one of the world's great walking regions, and we chose it deliberately: the landscape does half the work.

There's something about walking that loosens things.

When you move through a place at a human pace — your feet on ancient stone, the smell of crushed grass or Atlantic salt depending on the day, a village appearing around a bend that couldn't have been planned — thoughts 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.

Porto's Ribeira waterfront along the Douro river

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

Where eight days begins · Portugal · October 1–8, 2026

The investment

Your room

Canto do Sol has 14 rooms across two houses and a neighbouring apartment — each one private, each one distinct. We're welcoming 16 women, with two rooms configured for double occupancy. Single occupancy rooms are available in three tiers.

Everything is included and everything is handled. What that's worth — in money and in the time you won't spend planning — is part of what you're investing in.

Single occupancy

Tier 1	Private room, ensuite bathroom	$7,100 + GST
Tier 2	Private room, private bathroom just outside the room (includes 2 apartment-style rooms)	$6,800 + GST
Tier 3	Private room, shared bathroom	$6,400 + GST

Double occupancy

Travelling with a friend? Or open to the one you haven't met yet? Two rooms are available for double occupancy — shared space has a way of creating the conditions for the conversations that matter most.

Shared room

Per person, for women travelling together or open to sharing

$6,200 + GST

Double occupancy room at Canto do Sol — Peneda

Founding Member Places — Now Filled

The five Founding Member places have all been claimed. Standard pricing, shown above, applies to remaining places.

Room selection is first come, first served. The four Tier 1 rooms — each with a private terrace — are the most limited. If you're travelling alone and would like to be matched with a roommate, we'll do our best to accommodate that; roommate matching can't be guaranteed.

Payment schedule

A deposit of $2,500 is due upon enrollment to secure your place. The remaining balance is due in two equal installments — 50% due July 10, 2026, and the final payment due July 24, 2026. All prices are per person in Canadian dollars, plus GST.

Apply Now

We respond within 24 hours.

Not yet ready? Get on the list for updates.

Have a question? Let's talk.

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.

This retreat is not the right fit if you're looking for a structured program, professional support, or therapeutic services. This is a well-designed experience that removes noise and creates space. What you do with that space is yours.

Will I have my own room?

Most women have their own room. If you'd like to share, you have two paths: register together with a friend at the double-occupancy rate, or book your single room and ask to be matched with a roommate. If we're able to pair you, you'll both move to the double-occupancy rate and we'll refund the difference. If we can't, you simply keep your single room at the rate you booked — there's never an extra charge. Roommate matching can't be guaranteed, but asking costs you nothing.

What if my kids haven't left home yet, or retirement is nowhere in sight?

This retreat isn't tied to a particular birthday or an empty house. Some women feel the pull to design their next chapter when the nest empties. Others feel it years earlier — with a full house, a full calendar, and a quiet sense that something needs to shift sooner than "normal."

If you're asking yourself what you actually want now, you're not early and you're not late. There's no schedule to be on. You're welcome here, whatever season you're actually in.

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 Porto. 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 Porto 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'll spend the week at Canto do Sol — a family-owned eco-lodge in the hills above the Lima River, near Ponte de Lima, one of Portugal's oldest villages. Two houses and a neighbouring apartment, sweeping valley views, a natural pool, and a garden you'll eat from. The owners call the style "ecological boho-chic" — comfortable, considered, and rooted in this place. Not a hotel. Not a resort. Somewhere clearly made with love and a point of view.

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 — 16 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.

Why October?

October was chosen deliberately. The summer crowds are gone, the light is extraordinary, and the temperatures are made for walking — warm days, cool evenings. It's harvest season too, so the vineyards and local markets are at their best. You'll encounter Portugal as the people who live there experience it — not as it's packaged for July.

The retreat runs October 1–8, 2026. The group will be home by October 8th — in plenty of time for Canadian Thanksgiving weekend.

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.

Most women will fly into Porto (OPO), the closest major airport to the retreat. Lisbon (LIS) is also an option and may offer more convenient connections depending on where you're travelling from.

Airport transfers aren't included in the retreat investment, which gives you the flexibility to arrive early or stay longer — but transfer coordination for everyone arriving from either airport is handled for you. Once you land, we've got you.

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 Porto, a coastal escape, or something further afield. Just let us know.

Do I need a visa or anything special to enter Portugal?

Canadian passport holders do not need a visa to visit Portugal for stays of up to 90 days. Your passport should be valid for at least three months beyond your planned departure date from Portugal. When you arrive, your biometric data will be registered through the EU's Entry/Exit System (EES) — a quick process at the airport. If you're travelling on a non-Canadian passport, we recommend checking current requirements with your government's travel advisory.

What should I pack?

October in northern Portugal means warm days (around 18–22°C), cool evenings, and the occasional shower. Comfortable walking shoes, light layers, and a packable rain jacket are the essentials. We'll send a full packing list once you're confirmed.

What if I need to cancel?

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

Cancel before July 1, 2026: full refund, less a $500 administration fee.
Cancel July 2 – August 1, 2026: 50% refund.
Cancel after August 1, 2026: no refund.

If your place can be filled from the waitlist, we will refund your retreat fees less the $500 administration fee.

If we cancel the retreat for reasons within our control, you'll receive a full refund within 14 days. This is exactly why travel insurance with trip cancellation coverage is required to attend.

The team

While Jane designs what happens inside the experience, Lystra Germaine Sam designs everything that moves. Two people, two complementary bodies of work — one retreat that holds both.

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 13 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.

"Since 2015, Jane has arranged and facilitated five annual retreats for our management team. Her facilitation style is terribly well planned — and she injects a lovely sense of humour and attention to detail into every aspect. What started as a group of individuals in their own silos has become a cohesive team with a common sense of purpose."
— Roy Lamont, Client

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.

"Lystra is THE BEST! Her attention to detail, insight into local experiences, and ability to anticipate my needs in real time is why I've been using and recommending her luxury concierge travel and lifestyle services for years."
— Judi L., on Qmooniti Travel

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.

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

Not ready to apply yet?

Leave your email and we'll keep you posted — remaining availability, new departures, and a few things we don't share anywhere else.

From women who've been in the room

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

Aside from the amazing content and the warmth of Jane and her team, it was the people that attended the retreat. They were phenomenal. I have found a new family of like-minded people — and it helps a lot.

Daria B.

Retreat participant

"It gives you downtime. It gives you space. When I arrived I felt open and ready — removed from my environment, into this calm space with a balance of learning, relaxing, good food, and good company."

Joan W.

Retreat participant

"Jane asks really, really good questions. It made me dig deep and think about 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

Apply Now

We respond within 24 hours.

Not yet ready? Get on the list for updates.

Have a question? Let's talk.

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.

"Giving yourself permission to take a break from the day-to-day to look at the big picture is so important. Until you experience it, I don't think you get how important it is."

Nicole · Retreat participant

Walking. Talking. Portugal. · October 1–8, 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.

Apply Now

Not yet ready? Get on the list for updates.

The next chapter
is yours to design.

Something is changing

The women you'll walk with

Not a tour. Not a workshop. Something better.