When I first started planning our family trip to Greece, I didn’t expect the planning process itself to become such a profound lesson in mindfulness and letting go. But somewhere between refreshing flight comparison sites for the hundredth time and debating whether business class legroom was worth sacrificing a sunset dinner in Santorini, I realized that how I approached the planning would set the tone for the entire journey.

The Flight Dilemma: A Exercise in Priorities
Let me be honest—I was stressed. Finding flights for four people to Greece that checked all the boxes felt impossible. Affordable? Check. Convenient times? Maybe. Reasonable number of stops? Pick two out of three, apparently. And then there was the seductive whisper of business class comfort calling to me across the aisle.
I spent days weighing the pros and cons, spreadsheets open on multiple tabs, calculating exactly how many experiences we’d sacrifice for those lie-flat seats. Here’s what helped me find clarity:

Get clear on your values. I had to ask myself: What will I remember five years from now? The extra legroom on an overnight flight, or the cooking class in Athens where my son learned to make spanakopita? The answer became obvious. We were going to Greece to experience Greece, not to experience premium cabin service.
Honor your needs without judgment. That said, there’s no nobility in suffering. We looked for the sweet spot—economy seats with slightly more legroom, a tolerable number of connections, departure times that wouldn’t leave us zombies upon arrival. Comfort matters, but it doesn’t have to break the bank.

Staying Centered When the Details Overwhelm
Travel planning has a sneaky way of pulling you out of the present moment. I’d catch myself spiraling about logistics while my daughter was trying to tell me about her day, or lying awake at night mentally calculating travel insurance costs instead of actually sleeping.
Here’s what brought me back:
Breathe through the decision fatigue. When I felt overwhelmed by choices, I’d literally stop and take five deep breaths. Sounds simple, maybe even silly, but it works. Our brains can’t make good decisions when we’re in fight-or-flight mode over flight times.

Set boundaries with planning time. I gave myself dedicated windows to research—usually an hour in the evening—and then I closed the laptop. The flights would still be there tomorrow. My family’s presence wouldn’t be if I spent every evening hunched over TripAdvisor reviews.

Remember your why. I kept coming back to the real reason for this trip: creating memories with my mom, my husband, and my son. Sharing Greece’s beauty with the people I love most. That emotional anchor made the logistical stress feel smaller.

The Joy of Discovery (Thanks, TourRadar!)
While flights stressed me out, finding optional tours became the fun part of planning. TourRadar made it surprisingly easy to browse experiences—from wine tasting in Nemea to sunset sailing around the caldera. Having options clearly laid out, with reviews and prices transparent, took the anxiety out of this piece of the puzzle.
Pro tip: When booking tours, I learned to leave breathing room in the schedule. Yes, you want to see and do everything, but exhaustion isn’t Instagram-worthy. We built in mornings with no agenda, afternoons for wandering without a map, evenings for spontaneous taverna discoveries.

Self-Care Starts Before You Board the Plane
The biggest lesson I learned? Self-care during travel begins during the planning phase. Here’s how I protected my wellbeing while coordinating a multi-person international trip:
• Asked for help. My husband took over restaurant research. My mom, who’s traveled extensively, offered to map out a realistic daily itinerary. My son? He made us a playlist for the trip. Delegating wasn’t weakness—it was wisdom.
• Celebrated small wins. Flights booked? That deserved a toast. Hotels confirmed? Time for a celebratory coffee. Breaking the planning into milestone moments kept the excitement alive and the stress manageable.
• Practiced gratitude for the opportunity. In moments of frustration, I’d pause and acknowledge the privilege of being able to take this trip at all. Not everyone gets to agonize over which Greek island to visit—that’s a remarkably fortunate problem to have.

Being Present… Even in the Planning
The irony of planning future travel is that it can rob you of present-moment joy. But I found that mindful planning actually enhanced my anticipation. Instead of anxiously ticking boxes, I’d let myself daydream about walking through the Plaka, imagining the smell of souvlaki, picturing my son’s face when he first sees the Acropolis.

Practice gratitude now, not just later. I started a simple practice: each time I completed a planning task, I’d write down one thing I was grateful for about this upcoming adventure. “Grateful we’ll get to show our son the place where democracy was born.” “Grateful for the chance to travel with three generations.” It shifted planning from a chore to a meditation on abundance.

Final Thoughts: The Journey to the Journey
Looking back now, the planning process taught me as much as the trip itself would. It taught me to make decisions aligned with my values. To stay present even while planning for the future. To practice self-compassion when I felt overwhelmed. To share both the burden and the joy with the people I love.

Yes, I was stressed about the flights. Yes, the decisions felt overwhelming at times. But I was also excited—genuinely, deeply excited to share this experience with my mom, my husband, and my son. And that excitement, that gratitude, that love? Those were worth holding onto more tightly than any perfectly optimized itinerary.

Greece was waiting. And we were ready—not just with confirmed reservations and printed boarding passes, but with open hearts and a commitment to be fully present for whatever adventures awaited us.

Kalo taxidi! Safe travels—to Greece, and through the beautiful chaos of planning to get there.

What travel planning lessons have you learned? How do you stay centered when the logistics feel overwhelming? I’d love to hear your stories in the comments.