Come February, Linley and I will be packing our bags and heading off to San Miguel de Allende, Mexico for a 15-day workcation. I plan to relax, re-energize, and face some lingering fears after our last trip to San Miguel. Below I also share outfit details and my current favorite Madewell picks.
Two years ago, Linley, Davida, and I traveled to San Miguel de Allende. That visit blended a press trip with Avocados from Mexico and a bit of a workcation: ten days away to soak up sun, clear our heads, and try something different. We ate well, visited hot springs, wandered the town at our own pace, and enjoyed plenty of tequila and sangria. It was restorative in many ways, but it wasn’t without hiccups.
All three of us caught a severe stomach flu that knocked us out for several days. On top of that, I managed to break my foot while trail running. Looking back, the trip was a wild mix of delight and chaos. If you missed the full story from that trip, it makes for a funny but honest read about how travel can shift plans in unexpected ways.
This February, Linley, Mark, and I booked flights for another 15-day return to San Miguel. I don’t have a fear of the town itself, but since that last trip I’ve been working through anxieties connected to trail running and fitness after breaking my foot. The injury forced me to slow down and reassess how I train. I’ve always joked that I’m “prone to injury,” and in recent months that’s felt true — most recently I pulled my left glute doing weighted lateral lunges. It’s a reminder that overdoing it or missing small cues can set you back.
These physical setbacks have changed the way I approach exercise. Instead of pushing for every extra rep or daily intense session, I’ve moved toward a more measured routine: moderate workouts four to five days a week, more rest, and rehabilitation when needed. Those shifts weren’t easy at first. I had to learn that stepping back isn’t failure — it’s essential for long-term progress and wellbeing. My broken foot and the pulled glute have been blunt, effective teachers in that regard.
That’s part of why returning to San Miguel feels so right. I’m intentionally setting a softer schedule for this trip. My goals are simple and restorative: practice yoga every other day, follow Healthy Glow Guide workouts on select days, journal, and allow myself to wake up naturally without an alarm. I want to savor slower mornings, explore local markets at an unhurried pace, and return to Minnesota with more calm and balance than I left with.
We will be working during much of the trip — it’s a workcation, after all — but I’m aiming for a healthier blend of productivity and presence. I’d love to disconnect from the internet more than usual, but I also plan to share highlights so friends and readers can follow along. Balancing deadlines with downtime is a skill I’m still honing, and this trip feels like a good opportunity to practice it.
And now — for my outfit details!
Below are the pieces I’m planning to pack. The exact shoes I wore before are out of stock, but I’ve linked similar options I’m excited about. Madewell is currently running a promotion that makes it easy to save: spend a threshold amount and get a percentage off — a good time to pick up transitional pieces that travel well. Lightweight layers, comfortable jeans, and versatile tops are my travel essentials for San Miguel. The town’s charming streets and cooler evenings make a light jacket or cozy knit indispensable.
Top // Jeans // Shoes (similar)
My packing checklist focuses on versatility: a few easy tops, one pair of jeans that can be dressed up or down, comfortable walking shoes, a lightweight jacket, yoga clothes, and simple accessories. For work, I’ll bring a compact laptop setup and a lightweight notebook for journaling. I also plan to bring a small first-aid kit and items that support recovery — a foam roller strap, kinesiology tape, and a travel ice pack — just in case my body needs extra care while I’m away.
I’d love to know if you’re traveling soon and where you’re headed. Have you ever done a workcation? How do you balance work and downtime while traveling?