Short Vacations Made Her Feel Worse; Monthlong Working Holidays Helped

For the past three years, I have nursed a growing hatred for the standard two-week vacation.

In 2023, I took an adult gap year with my husband, Nick. After a year filled with safaris in East Africa, learning to haggle in Morocco, and island hopping in Southeast Asia, we returned home to LA and feverishly rebuilt our lives.

I made reluctant peace with the fact that our future travel ambitions would have to fit into neat two-week sprints by obsessively planning.

Our first vacation after coming home

The itinerary was simple. We’d start by visiting two Greek islands: Syros, where we’d join a multi-day cooking school, and Paros, where we’d lounge around on the beach. Then we’d fly to Malta to explore historical sites before closing out the trip with a weekend layover in Dublin, one of our favorite places in the world.

At first, the trip seemed like a success. Our hard-earned travel skills were well-utilized. We breezed through the airport with one backpack each.

Syros, our first stop, was pleasantly calm — filled with pottery stores I loved to peruse. The cooking school was intimate and involved — ideal for experienced cooks like us.

But when cooking school was over, a few days into our trip, the two-week clock began to nag at me, instilling pressure to make the most of any free time.

Each subsequent activity that didn’t fill my soul felt like an incrementally larger catastrophe. Snorkeling in barren, over-fished waters was a waste of an afternoon. Beach days marred by clouds and chilly water were a disaster. And eating at a slew of disappointing restaurants in Malta was the tragedy of the century.

Returning home after vacation

When our plane home touched down in LA, I was filled with dread. The thought of opening my work laptop the next day was already taunting me. Worse, I realized that feeling of dread was familiar. I’d felt this way coming home from virtually every vacation I’d taken before. I’d always accepted it as a given.

I’d accepted that a vacation could leave me feeling worse than when I’d left. But what was the point of that?

There had to be something we could do to change this dynamic. This became a recurring late-night conversation between my husband and me. “Setting aside our adult gap year, did we ever take a trip where we came back happier than we left?” I asked him one night.

“Yeah, Alaska,” Nick said without hesitation. The answer didn’t surprise me; he’s an outdoorsman. “But that wasn’t really a vacation.”

Years earlier, we’d spent a month in Alaska during the summer. We were working remotely, but it didn’t feel like work. We used a long weekend to explore huge stretches of the state — camping beside a glacier on the Kenai Peninsula with no one else around, watching grizzly bears in Denali National Park, and listening to audiobooks together on long drives back to Anchorage.

Working during the trip wasn’t always convenient, but the slight time difference gave me more uninterrupted time to focus. And with the sun setting so late, our evenings felt expansive. We hiked local trails, tried many must-visit restaurants, and wandered through art galleries around Anchorage.

Having something to look forward to each night made it easier for me to log off at a reasonable hour — something I struggled with at home. Best of all, staying plugged into daily life meant I didn’t dread returning.

That’s when it hit me: We should do it again.

A monthlong working holiday instead

I pitched the idea to Nick — skip a typical two-week vacation so that we could explore more deeply without the pressure to maximize every moment. We’d still take time off, but spread it out. He was in.

In January of this year, we put the idea to the test and spent a month in the South of France. Nick got the arrangement approved at work without issue. I had since launched my own boutique travel company, Travelries, and dutifully approved my own working arrangement.

While working, we fell into a rhythm

In Nice, we woke up to the smell of fresh baguettes, shopped for groceries at picturesque local markets, and once a week picked a new seaside town in the French Riviera to visit for dinner.

On weekends, we took the train to other regions — bopping between villages in Provence, Monaco, and the Italian Riviera, admiring the glittering coastal views along the way.

We never felt rushed, but by the end of the month, we’d visited more than 20 towns. We wrapped the trip with a long weekend in Paris, where I’d once studied abroad and now got to play tourist.

This time, the trip home didn’t come with the usual dread. We were sad to leave Nice, but we felt full. And instead of bracing for reality, I was already thinking about where we’d go next.