This is what I imagine winter in Portugal looks like.
Winter is a soft reminder that all things come to an end.
This desire for reflection brought me back to our three trips to Portugal. Those trips form a kind of story arc, a single metaphor for how our understanding evolves over time.. The first trip was all excitement, overwhelm, and possibility. It was new and a little scary, but we dove in anyway. The second trip was easier and far less planned. We left more open so we could be freer, and that openness felt like the white space in a painting or the silence between musical notes. White space matters. If you fill a vacation down to the minute, what is left to notice? Still, that trip could have used a little more structure. And then came the third trip, the one where I went alone to begin the process of buying the cottage in the Algarve. It was full of details and decisions, yet still held enough space for Bengil Caves, a couple of Algarve castles, and wandering with no agenda. There was less pushing to see everything and more letting Portugal reveal herself to me. Across the three trips, it became clear: the notes of the symphony matter, and so does the space between them. Finding the balance is its own kind of art.
Portugal Trips as a Story Arc
Benagil Cave, Photo by Wendy Stieg
Planning a trip is just one expression of something bigger: the deeper work of building a life. Build asks us to create structure, but not rigidity. To welcome possibility, but not chaos. To hold clarity and curiosity at the same time. Portugal taught me that building anything meaningful, be it a trip, a home, a future, requires both intention and openness. It isn’t about getting everything perfect; it’s about finding a balance that lets the experience breathe. There is something magic about letting go. Allowing life to just be what it is. Can you let yourself have more whitespace in your trip? It is something to think about as we end this year.
What We Build Beyond the Itinerary
Faro, Portugal. Photo by Wendy Stieg
December’s Blueprint
You are only free when you realize you belong no place—you belong every place—no place at all. — Maya Angelou
As we move toward the close of the year, I find myself thinking about everything behind us, the ups and downs, the surprises, the accomplishments, and the deep sense that we can overcome anything. December creates its own paradox: part of us looks back while another part feels ready to hit the ground running. Holding both at once isn’t uncomfortable, but it does create a pull in two directions. Learning to stay in that space, to let uncertainty exist without resisting it, takes practice. Yet I’m beginning to notice that something shifts when I do. On the other side of those opposing feelings, a workable plan often emerges. If you missed the reflection that started this month’s flow, you can read December’s Muse here. This month’s December Blueprint, the Build Phase in our Life Notes flow, explores that very paradox: how creating a plan is both active and deeply internal at the same time.
In Closing
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Castelo de São João do Arade, Ferragudo, PT
Photo by Wendy Stieg
So how does all of this connect to planning a trip? In every way. Most people try to pack in every minute, hoping to squeeze the most value out of their time, but that often means missing the subtleties that make travel unforgettable. The old version of planning fills every second; the newer version invites something different. It asks for intentional, flexible, intuitive planning. This means a curated trip rather than a crammed one. You will have uncomfortable moments. You will make mistakes. You won’t see everything. Let some of that be okay. A little letting go creates space for the unexpected, and that’s where the real magic happens. Planning a beautiful vacation is art: the plan is the image, and the freedom around it is the white space in the painting. When you allow both, the experience becomes beautiful, surprising, a little scary, deeply comforting. And yes, occasionally uncomfortable. But you return home changed, seeing life through new eyes. Spacious planning gave us some of our most unforgettable moments in Portugal, and now we can’t wait for the next journey.
A Curated Trip is Art
View of the Guadiana River, and Spain, Vila Real de Santo Antonio
Photo by Wendy Stieg
As we close the year, I’m reminded that building a meaningful life happens in the same way: a little structure, a little mystery, and enough whitespace to let the beauty in. December asks us to pause, reflect, and gently imagine what comes next, not with pressure, but with curiosity. My hope is that you carry this idea with you into the new year: create the shape of the journey, but leave room for the unexpected. Let your plans breathe. Let life reveal itself to you. That is where the art lives.
Life is either a daring adventure or nothing at all. —Helen Keller
November’s Blueprint
I remember watching Northern Exposure years ago, and there was this episode where Holling Vancoeur got incredible pleasure from paint-by-number paintings. He could whip them out and suddenly have a whole stack of finished work, and it made him so happy. In no time at all, he could skip the journey and arrive at the destination.
Enter Chris Stevens, the philosophical DJ from KBHR. He talks Holling into burning all the paintings because he believed Holling would be much happier slowing the process down and creating something of his own. If memory serves, Holling wasn’t having it. He wanted the joy of that quick finish, skip the messy stuff in the middle and jump right to the perfect painting. Chris wanted him to have a deeper experience, but Holling wanted none of it.
At that time in my life, I was definitely on Holling’s side. I was horrified by Chris’s suggestion for his bar-owning friend. I bring this story up because planning an incredible trip isn’t about skipping the messy middle. Most of us adventurers know that the middle is where the joy and the stories live. I’m always amazed at how fast trips go, and I want to savor every moment.
The joy of travel begins long before you leave home. When you plan by feel instead of pressure, the “messy middle” becomes where the magic lives.
So let’s rethink this. Instead of overwhelm, think like an adventurer. Allow whatever you feel to be there, and plan anyway. There is a place for traditional planning methods, but try planning by feel. This more intuitive approach lets you get not just what you think you want out of your trip, but so much more.
We took one of our trips to Portugal and did the whole thing by feel. We rented a VW California from Siesta Campers and did a combination of camping, renting camper space from locals, and sometimes just parking wherever for the night. I still needed periodic hotel time, showers and real beds were definitely appreciated!
There were times during that trip when we had more downtime than usual, but we found ourselves in some truly unusual places. We camped in Carlos’s yard outside Sintra, with sheep as our neighbors. We stayed outside Carmona in Spain with other travelers, in a spot definitely not designed for overnight stays, and waking up to the sunrise and a short walk to espresso and pastries in the town square was priceless. And deciding on a whim to drive up to Alcoutim and stay at the Hotel d’Alcoutim just because I wanted a shower turned out to be amazing.
This month I am focusing on staying positive. My monthly “Muse” article, November’s Muse, outlines simple ways to catch yourself and redirect your thoughts so you can stay grounded. Getting your mind right has to come first. Whether you’re planning a big life event, traveling to a faraway destination, or figuring out your next career or retirement move, planning is inherently stressful.
From the mindset of redirecting yourself toward positivity, start by just acknowledging that. Then let it go. Breathe. Allow the fun part of all of this to guide you. Approach life as an adventurer, knowing that the bumps along the way. Even challenges in the planning process, and those bumps along the way are what color the whole experience.
So let go. Allow your feelings to guide you instead of a whole bunch of “shoulds.”
I do have some simple steps, because for some people, having steps feels grounding. But keep in mind: the more you can allow and let go, the richer your experience will be.
How to Plan Your Trip by Feel
If you’re ready to plan your next trip without overwhelm, here’s the simplest way to do it — and it all comes back to feeling your way forward instead of forcing anything.
1. Notice what kind of energy you have today.
Are you in “dreaming” mode, where ideas come easily?
Or “doing” mode, where you can handle one small task?
There’s no right answer, just notice where you are.
2. Take the smallest step that matches your energy.
If you’re inspired: browse destinations, read blogs, save photos.
If you’re grounded: check a date, look at a flight, set one alert.
If you’re tired: pause. Planning from exhaustion never feels good.
3. Choose one “anchor idea” for your trip.
Not a full itinerary, just the thing that excites you most.
A city you love, a beach you want to try, a feeling you want the trip to have.
Let that be enough for now.
4. Let the rest unfold over time.
Your intuition will fill in the blanks.
You don’t need to know everything today.
Planning by feel means trusting the next step will show up when you’re ready.
5. Keep the process light, and stay curious.
The messy middle, the unexpected detours, the little surprises…
that’s usually where the real joy of travel lives.
Let yourself enjoy the journey of planning as much as the trip itself.
At the end of the day, planning isn’t about perfection, it’s about feeling your way toward the experiences that light you up. When you stop trying to control every detail and allow yourself to move at the pace of your own energy, the whole process becomes softer, more joyful, and so much more aligned. Whether you’re dreaming big or taking the tiniest step forward, trust that it all counts. And trust that your next adventure will unfold exactly the way it’s meant to.
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San Lucar, Spain
View of San Lucar, and the Guadiana River from Alcloutim, Portugal
"Start where you are. Use what you have. Do what you can" —Arthur Ashe
The map begins to unfold: a quiet plan taking form beneath the dreams that sparked it.
October’s Blueprint
It all began with a dream. Dreams do become reality, but as the architect of your life, it’s time to give that dream structure. Where is your dream destination? How will you get there? What steps do you need to take to turn it into a plan?
Start by checking flight options three to six months ahead for the best prices. Compare lodging types to find what fits your travel style and budget. Learn a few key phrases in the local language, enough to navigate restaurants and shops. Begin organizing important details such as your passport, transportation, and travel insurance. Research local customs and jot down ideas for must-see sights and hidden gems. Every small step builds confidence and brings your travel dream closer to reality. And remember, for any dream to become a reality, you keep moving toward it until you reach it!
