Unconventional Rules for Traveling and Living Better (That I Wish I Knew Sooner)

If I could use a time machine to give my younger self a few life and travel rules, the first thing I'd say is simple: take a deep breath and slow down.

When I first started to travel and explore the world, I had my long lists of must-do, must-see attractions, restaurants, experiences. I was determined to check off every single tourist box. There's too much of the world to see. I have to make my visit to XYZ country count, right? And since I was going to be taking pictures, I needed to wear stylish clothes, pack for a variety of scenarios, and pack my schedule until midnight. How exhausting!

Now that I'm older, wiser, and significantly more relaxed, I've realized that the best experiences are the result of slowing down and setting boundaries. Here are some things I know now that I wish I understood when I was younger:

First, the return trip is always better. Revisiting a country that you’ve already been to means that the pressure of seeing the "city highlights" is totally gone. You can actually take your time and absorb the vibe and take it in at your own pace. I love seeking out local libraries and bookstores an immersing myself in a local community (even if that means that I'm buying more books than I can possibly read!) I’ve also learned to prioritize the things that elevate the experience. For me, that means building an entire day’s itinerary around a hard-to-get restaurant or speakeasy reservation. I LOVE a good speakeasy! The experience is always worth it.

When I visit a local bar or restaurant, I ask sometimes ask the bartender to surprise me with a custom cocktail (I give them one base ingredient, like pineapple juice or gin, and trust their art).

Another MUST DO when I travel is to splurge on the arrival transfer. After hours of flying, then getting through customs, then baggage claim, seeing your name on that sign is instant peace.

And above all, protect your peace. Fly in comfy clothes. Normalize making zero plans after 8:00 PM. Say yes to spontaneous excursions!

And no matter where you are in the world, find pieces of home. For me, hearing Tagalog when I’m in a foreign destination always makes me stop and eavesdrop. I promise I won't tell your secrets. For me, it's the fastest way to feel connected to my family, even a million miles away.

Grace A Cular Yee is the founder and lead travel strategist at Pineapple7, where she transforms the chaos of modern travel into seamless, intentional exploration. With a focus on bespoke curation and precision logistics, she helps high-achievers reclaim their time and reconnect with the world through meaningful, high-integrity journeys. Ready to plan your next chapter?